Biorenewable, water-degradable polymers and co-polymers
View Patent ↗Various embodiments relate to biorenewable and water-degradable co-polymers and methods of producing co-polymers that include a plurality of first monomeric units and a plurality of second monomeric units joined by a plurality of hydrolytically-sensitive ester linkages. Each of the plurality of first monomeric units may be derived from a first monomer. The first monomer may be the product of a reaction between itaconic acid and a first amino acid. Each of the plurality of second monomeric units may be derived from a second monomer. The second monomer may be the product of a reaction between itaconic acid and a second amino acid. The co-polymers may be a product of the reaction of the first monomer and the second monomer in the presence of a diol. The co-polymers may have a glass transition temperature of about 50° C. or greater.
1. A co-polymer, having a glass transition temperature of about 50° C. or greater, the co-polymer comprising: a plurality of first monomeric units and a plurality of second monomeric units joined by a plurality of hydrolytically-sensitive ester linkages,
wherein each of the plurality of first monomeric units is derived from a first monomer,
wherein the first monomer is the product of a reaction between itaconic acid and a first amino acid,
wherein each of the plurality of second monomeric units is derived from a second monomer,
wherein the second monomer is the product of a reaction between itaconic acid and a second amino acid, and
wherein the co-polymer is a product of the reaction of the first monomer and the second monomer in the presence of a diol.
2. The co-polymer of claim 1 , wherein the first amino acid is substituted or unsubstituted para-aminobenzoic acid.
3. The co-polymer of claim 1 , wherein the second amino acid is a natural or non-natural substituted or unsubstituted aliphatic amino acid.
4. The co-polymer of claim 1 , wherein the second amino acid is glycine.
5. The co-polymer of claim 1 , wherein the diol is a 1,3-diol, a 1,4-diol, or a-1,5 diol.
6. The co-polymer of claim 1 , wherein the diol is 1,3-propanediol.
7. The co-polymer of claim 1 , wherein 94% or more of the plurality of hydrolytically-sensitive ester linkages are hydrolyzed after one year of exposure to water.
8. The co-polymer of claim 1 , wherein the first monomeric unit and the second monomeric unit are present in a 1:1 ratio.
9. The co-polymer of claim 1 , wherein the first monomeric unit and the second monomeric unit are present in a ratio that is not 1:1.
10. The co-polymer of claim 1 , wherein the first amino acid is para-aminobenzoic acid and the second amino acid is glycine.
11. The co-polymer of claim 1 , wherein the first amino acid is para-aminobenzoic acid, the second amino acid is glycine, and the diol is 1,3-propanediol.
12. A co-polymer, comprising a first repeating unit having a structure according to formula I:
and a second repeating unit, having a structure according to formula II:
wherein R is a C 1 to C 6 aliphatic group;
wherein the co-polymer has a glass transition temperature of about 50° C. or greater.
13. The co-polymer of claim 12 , wherein the first repeating unit and second repeating unit are present in a 1:1 ratio.
14. The co-polymer of claim 12 , wherein the first repeating unit and second repeating unit are present in a ratio that is not 1:1.
15. The co-polymer of claim 12 , wherein the first repeating unit and the second repeating unit are joined by a hydrolytically-sensitive ester linkage.
16. The co-polymer of claim 15 , wherein 94% or more of the hydrolytically-sensitive ester linkages are hydrolyzed after one year of exposure to water.
17. A method of producing a co-polymer, having a glass transition temperature of about 50° C. or greater, the method comprising: reacting a first monomer and a second monomer in the presence of a diol,
wherein the first monomer is the product of a reaction between itaconic acid and a first amino acid;
wherein the second monomer is the product of a reaction between itaconic acid and a second amino acid; and
wherein, in the co-polymer, the first monomer and second monomer are joined by a hydrolytically-sensitive ester linkage.
18. The method of claim 17 , wherein 94% or more of the hydrolytically-sensitive ester linkages are hydrolyzed after one year of exposure to water.