POLYMERS AND METHODS OF PRODUCING THEREOF
Provided herein are methods of producing polymers from furan and optionally diol compounds, using an organocatalyst. A polymer composition comprising a polymer prepared by the method is contemplated. Provided herein are also polymer compositions, such as poly(alkylene-2,5-furandicarboxylate). In some embodiments, polymer compositions have any one of the characteristics discussed herein, or any combinations thereof.
1 . A composition comprising a polymer with a polymer backbone,
wherein the polymer backbone comprises an optionally substituted furandicarboxylate moiety or an optionally substituted tetrahydrofurandicarboxylate moiety,
wherein the composition is free from metal catalysts or residues thereof;
wherein the composition has an number average molecular weight of at least 10,000 Da; and
wherein a solution of 5 mg/mL of the composition has an absorbance of less than 0.05 at 400 nm.
2 . A composition comprising a polymer with a polymer backbone,
wherein the polymer backbone comprises an optionally substituted furandicarboxylate moiety or an optionally substituted tetrahydrofurandicarboxylate moiety,
wherein the composition has a metal content that does not come from metal catalysts used to produce the polymer or precursors thereof, and wherein a solution of 5 mg/mL of the composition has an absorbance of less than 0.05 at 400 nm.
3 . The composition of claim 1 , wherein the metal catalysts are transesterification catalysts.
4 . The composition of claim 1 ,
wherein the composition has a total metal content of less than 0.1 wt %.
5 . The composition of claim 4 , wherein the total metal content includes the content of transition metals, post-transition metals, metalloids, or lanthanoid metals, or any combinations thereof.
6 . The composition of claim 4 , wherein the total metal content excludes the content of alkali metals, alkaline earth metals, and silicon.
7 . The composition of claim 1 , wherein the optionally substituted furandicarboxylate moiety is an optionally substituted 2,5-furandicarboxylate moiety, and the optionally substituted tetrahydrofurandicarboxylate moiety is an optionally substituted 2,5-tetrahydrofurandicarboxylate moiety.
8 . The composition of claim 1 , wherein the optionally substituted furandicarboxylate moiety is:
9 . The composition of claim 1 , wherein the polymer is poly(alkylene-2,5-furandicarboxylate) or poly(alkylene-2,5-tetrahydrofurandicarboxylate).
10 . The composition of claim 9 , wherein the polymer is poly(ethylene-2,5-furandicarboxylate) or poly(ethylene-2,5-tetrahydrofurandicarboxylate).
11 . A method, comprising polymerizing a furan or tetrahydrofuran in the presence of an organocatalyst to produce a polymer composition,
wherein the furan or tetrahydrofuran is a compound of formula (G):
wherein:
is a double bond or a single bond;
j is 2 when is a double bond, or j is 6 when is a single bond j;
each R n is independently H or alkyl; and
each R g is independently alkyl, and
wherein
a) the furan or tetrahydrofuran is polymerized in the presence of an organocatalyst and an antioxidant; or
b) the furan or tetrahydrofuran is polymerized at a temperature of less than 200° C.;
or a combination of a) and b); and
wherein the polymer composition comprises a polymer with a polymer backbone, wherein the polymer backbone comprises a moiety of formula (Q′):
wherein , j is 2, R n and R g are as defined above for formula (G); and
wherein a solution of 5 mg/mL of the composition has an absorbance of less than 0.05 at 400 nm.
12 . The method of claim 11 , wherein the organocatalyst is generated in situ.
13 . The method of claim 11 , wherein the organocatalyst is a non-transition metal catalyst, a non-post-transition metal catalyst, a non-metalloid catalyst, or a non-lanthanoid catalyst, or any combinations thereof.
14 . The method of claim 11 , wherein the organocatalyst is an N-heterocyclic carbene.
15 - 21 . (canceled)
22 . A polymer composition produced according to the method of claim 11 , wherein a solution of 5 mg/mL of the composition has an absorbance of less than 0.05 at 400 nm.
23 . The polymer composition of claim 1 , wherein the solution is in hexafluoroisopropanol.
24 . The method of claim 11 , wherein the solution is in hexafluoroisopropanol.
25 . A composition comprising a poly(ethylene-2,5-furandicarboxylate) (PEF) and a N-heterocyclic carbene residue.
26 . The composition of claim 25 , wherein the composition further comprises an antioxidant residue.
27 . The composition of claim 25 , wherein the composition has an average molecular weight of at least 10,000 Da.
28 - 30 . (canceled)