Recyclable and reconfigurable high-performance polymer networks and uses thereof
AssigneeThe Regents of the University of California
InventorsBrett A. Helms, Peter R. Christensen
Life of this patent
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Abstract
The present invention relates to a composition of polymers comprising dynamic covalent diketoenamine bonds. This composition allows the formulation of polymeric materials with a wide range of architectures and properties, and further allows these materials to be recycled using thermal, chemical, or mechanical processes.
Claims6
A composition comprising a polymer, or polymer network, having at least one unit of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), and/or (XX), or a mixture thereof;
- wherein said polymer, or polymer network, is obtained by connecting one compound Y comprising at least two functional groups selected from the group (A), (B), (C), (D), (E), (F), (G), (H), (I), (J), (K), (L), (M), (N), (O), (P), (Q), (R), (S), (T), (U), (V), and/or (W), or a mixture thereof;
- with at least one compound Z comprising at least two amine functional groups of the type —NH2, —NHR4, —NH3+ and/or —NHR4R5+ groups, or at least two functional groups that generates —NH2, —NHR4, —NH3+ and/or —NHR4R5+ in situ, or a mixture thereof;
- wherein said amine is optionally (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero (C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- or heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl, moiety, said heteroatoms being each independently a C, Si, chalcogenide, or a pnictide;
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero (C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and
- heteroaryl(C1-20)alkyl, can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero (C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, can be unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero (C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- —NO2;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4, and
- wherein the ratio R is less than, or equal to 1 (R≤1), where R=(sum (functionality of compound Y (FY)×number of moles of compound Y (NY))/(sum (functionality of compound Z (FZ)×number of moles of all molecules of compound Z (NZ)):
- R
- =
- ∑
- F
- Y
-
- N
- Y
- ∑
- F
- Z
-
- N
- Z
- ≤
- 1
- ;
- wherein R1 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictid);
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-2)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4, —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein R2 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenid), or a pnictid);
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-2)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein R2 and R3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R2 and R3 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein each said heterocyclyl;
- or heteroaryl is independently optionally substituted with one or more Z2 wherein each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4, —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4, —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- wherein R2 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R2 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein X1 and R2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;
- wherein X1 and R3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-2)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NRSS(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4,
- wherein R3 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- wherein each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4, and
- wherein R3 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R3 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5, —SR5;
- —S(O)R4, —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4
- wherein R3 is linked to R1 with a linker X1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4, —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O);
- R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- each R4 is independently selected from the group consisting of hydrogen, C(1-20)alkyl, C(2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)akyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- each R5 is independently selected from the group consisting of hydrogen, (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- each R6 and R7 is independently selected from the group consisting of hydrogen;
- (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- or wherein R6 and R7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.
A method for synthesizing a polymer from one or more precursors in one or more solvents, said method comprising:
- (a) dissolving, dispersing, or suspending one or more precursors individually in the same solvent, or individually in different and/or separate solvents, optionally with one or more surfactants;
- (b) optionally heating the solvent or one or more solvents of the different and/or separate solvents;
- (c) mixed the solvent comprising the one or more precursors together to form a polymer;
- wherein said polymer has at least one unit of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), and/or (XX), or a mixture thereof;
- wherein said polymer, or polymer network, is obtained by connecting one compound Y comprising at least two functional groups selected from the group (A), (B), (C), (D), (E), (F), (G), (H), (I), (J), (K), (L), (M), (N), (O), (P), (Q), (R), (S), (T), (U), (V), and/or (W), or a mixture thereof;
- with at least one compound Z comprising at least two amine functional groups of the type —NH2, —NHR4, —NH3+ and/or —NHR4R5+ groups, or at least two functional groups that generates —NH2, —NHR4, —NH3+ and/or —NHR4R5+ in situ, or a mixture thereof;
- wherein said amine is optionally (C1-20)alkyl, (C2-20)alkenyl), (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C2-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- or heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl, moiety, said heteroatoms being each independently a C, Si, chalcogenide, or a pnictide;
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O);
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- can be unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen:
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2R6R7;
- —NO2;
- —NR5C(O)R4;
- —NR5S(O)R4;
- NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein the ratio R is less than, or equal to 1 (R≤1), where R=(sum (functionality of compound Y (FY)×number of moles of compound Y (NY))/(sum (functionality of compound Z (FZ)×number of moles of all molecules of compound Z (NZ)):
- R
- =
- ∑
- F
- Y
-
- N
- Y
- ∑
- F
- Z
-
- N
- Z
- ≤
- 1
- ;
- wherein R1 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictid);
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-2)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4, —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —COR5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein R2 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenid), or a pnictid);
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O);
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- NR5C(O)2NR6R7;
- NR6R7;
- cyano;
- —COR5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein R2 and R3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R2 and R3 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein each said heterocyclyl;
- or heteroaryl is independently optionally substituted with one or more Z2 wherein each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl(C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)R4, —NR5C(O)NR6R7, NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- wherein R2 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R2 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein X1 and R2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;
- wherein X1 and R3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R3;
- —C(O)NR6R7;
- and —C(O)R4;
- wherein R3 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alky);
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O);
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- wherein each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and C(O)R4;
- and
- wherein R3 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R3 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5, —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4, —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- wherein R3 is linked to R1 with a linker X1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- each R4 is independently selected from the group consisting of hydrogen, C(1-20)alkyl, C(2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- each R5 is independently selected from the group consisting of hydrogen, (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- each R6 and R7 is independently selected from the group consisting of hydrogen;
- (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S—O or S(O)2;
- or wherein R6 and R7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.
A method for synthesizing a polymer by melting one or more solid precursors, said method comprising:
- (c) melting one or more precursors together to form a polymer, wherein at least one precursor is solid prior to melting;
- (d) optionally mixing the one or more precursors are solids prior to, during, and/or subsequent to the melting step, or melting the precursors which are solid are optionally first melted individually then mixed together to form a polymer;
- wherein optionally the melting of the one or more precursors is in a single or twin screw compound extrusion device;
- wherein said polymer has at least one unit of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), and/or (XX), or a mixture thereof;
- wherein said polymer, or polymer network, is obtained by connecting one compound Y comprising at least two functional groups selected from the group (A), (B), (C), (D), (E), (F), (G), (H), (I), (J), (K), (L), (M), (N), (O), (P), (Q), (R), (S), (T), (U), (V), and/or (W), or a mixture thereof;
- with at least one compound Z comprising at least two amine functional groups of the type —NH2, —NHR4, —NH3+ and/or —NHR4R5+ groups, or at least two functional groups that generates —NH2, —NHR4, —NH3+ and/or —NHR4R5+ in situ, or a mixture thereof;
- wherein said amine is optionally (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- or heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl, moiety, said heteroatoms being each independently a C, Si, chalcogenide, or a pnictide;
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- can be unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen:
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)R4;
- —SO2NR6R7;
- —NO2;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein the ratio R is less than, or equal to 1 (R≤1), where R=(sum (functionality of compound Y (FY)×number of moles of compound Y (NY))/(sum (functionality of compound Z (FZ)×number of moles of all molecules of compound Z (NZ)):
- R
- =
- ∑
- F
- Y
-
- N
- Y
- ∑
- F
- Z
-
- N
- Z
- ≤
- 1
- ;
- wherein R1 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictid);
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-2)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4, —NR5S(O)2R4;
- —NR5C(O)NR6R7, NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein R2 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenid), or a pnictid);
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-2)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen:
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein R2 and R3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R2 and R3 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein each said heterocyclyl;
- or heteroaryl is independently optionally substituted with one or more Z2 wherein each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8) cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4, —NR5C(O) NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- wherein R2 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R2 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein X1 and R2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;
- wherein X1 and R3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4, —NR5C(O)NR6R7, NR6R7;
- cyano;
- —CO2R5;
- C(O)NR6R7;
- and —C(O)R4;
- wherein R3 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero (C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and
- heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- wherein each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)R4;
- —SO2NR6R7;
- nitro;
- NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7, NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O) R4;
- and
- wherein R3 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R3 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5, —SR5, —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7, NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4
- wherein R3 is linked to R1 with a linker X1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl(C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5, —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- each R4 is independently selected from the group consisting of hydrogen, C(1-20)alkyl, C(2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- each R5 is independently selected from the group consisting of hydrogen, (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- each R6 and R7 is independently selected from the group consisting of hydrogen;
- (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl(C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- or wherein R6 and R7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.
A method for synthesizing a polymer from one or more precursors using mechanical grinding, said method comprising:
- mixing one or more said precursors together in a shaking or rotating chamber to form a polymer;
- wherein said shaking or rotating chamber is optionally a ball mill,
- wherein optionally said shaking or rotating chamber contains a grinding medium;
- wherein said grinding medium optionally comprises of one or several sizes of spheres or rods made of metallic, composite, ceramic, or polymer materials;
- wherein said precursors are optionally dissolved in a solvent prior to mechanical grinding in said rotating chamber, also optionally called a ball mill;
- wherein said precursors are optionally mixed together in a solvent during mechanical grinding;
- wherein if one or more precursors are solids, precursors are optionally melted together before mixing;
- wherein the duration of mixing of precursors within said shaking or rotating chamber, optionally with said grinding medium, is used to control the extent of polymerization;
- wherein the duration of mixing of said precursors within said shaking or rotating chamber is used to control polymer properties;
- wherein said polymer properties may optionally include the glass transition temperature (Tg), polymer solubility, modulus, tensile strength, polymer color, polymer toughness, polymer rigidity;
- wherein said polymer has at least one unit of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), and/or (XX), or a mixture thereof;
- wherein said polymer, or polymer network, is obtained by connecting one compound Y comprising at least two functional groups selected from the group (A), (B), (C), (D), (E), (F), (G), (H), (I), (J), (K), (L), (M), (N), (O), (P), (Q), (R), (S), (T), (U), (V), and/or (W), or a mixture thereof;
- with at least one compound Z comprising at least two amine functional groups of the type —NH2, —NHR4, —NH3+ and/or —NHR4R5+ groups, or at least two functional groups that generates —NH2, —NHR4, —NH3+ and/or —NHR4R5+ in situ, or a mixture thereof;
- wherein said amine is optionally (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- or heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl, moiety, said heteroatoms being each independently a C, Si, chalcogenide, or a pnictide;
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- can be unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen:
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- —NO2;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4, and
- wherein the ratio R is less than, or equal to 1 (R≤1), where R=(sum (functionality of compound Y (FY)×number of moles of compound Y (NY))/(sum (functionality of compound Z (FZ)×number of moles of all molecules of compound Z (NZ)):
- R
- =
- ∑
- F
- Y
-
- N
- Y
- ∑
- F
- Z
-
- N
- Z
- ≤
- 1
- ;
- wherein Riis selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictid);
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-2)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O) NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein R2 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety each heteroatom is independently a C, Si, chalcogenid), or a pnictid);
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and/or heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- each Z1 is independently selected from the group consisting of halogen:
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- and
- wherein R2 and R3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R2 and R3 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein each said heterocyclyl;
- or heteroaryl is independently optionally substituted with one or more Z2 wherein each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8) cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8) cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O)NR6R7, NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- wherein R2 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R2 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein X1 and R2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;
- wherein X1 and R3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- NR5C(O)R4;
- —NR5(O)2R4, —NR5C(O)NR6R7, NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and C(O)R4;
- wherein R3 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
- (C2-20)alkynyl;
- (C6-12)aryl, (C3-8)cycloalkyl;
- (C6-12)aryl(C1-20)alkyl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- hetero(C1-20)alkyl;
- heterocyclyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;
- wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and
- heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is unsubstituted or substituted with one or more Z1;
- wherein each Z1 is independently selected from the group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR6R7;
- nitro;
- —NR5C(O)R4:—NR5S(O)2R4;
- —NR5C(O) NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)2NR6R7;
- and C(O)R4;
- and
- wherein R3 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein R3 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5, —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- NR5C(O)R4;
- —NR5S(O)2R4, —NR5C(O) NR6R7;
- NR6R7;
- cyano;
- —CO2R7;
- —C(O)NR6R7;
- and —C(O)R4
- wherein R3 is linked to R1 with a linker X1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;
- wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;
- wherein each said heterocyclyl;
- or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
- (C1-20)alkyl;
- (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl(C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- (C3-8)cycloalkyl(C1-20)alkyl;
- heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl;
- halo(C1-20)alkyl;
- halo(C1-20)alkyloxy;
- —OR5;
- —SR5;
- —S(O)R4;
- —S(O)2R4;
- —SO2NR5R6;
- nitro;
- —NR5C(O)R4;
- —NR5S(O)2R4;
- —NR5C(O) NR6R7;
- NR6R7;
- cyano;
- —CO2R5;
- —C(O)NR6R7;
- and —C(O)R4;
- each R4 is independently selected from the group consisting of hydrogen, C(1-20)alkyl, C(2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- each R5 is independently selected from the group consisting of hydrogen, (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- each R6 and R7 is independently selected from the group consisting of hydrogen;
- (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
- (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;
- and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
- heterocyclyl;
- heteroaryl;
- heterocyclyl(C1-20)alkyl;
- and heteroaryl(C1-20)alkyl;
- is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
- or wherein R6 and R7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.
Dependencies are inferred from the claim text.