High molecular weight stereoregular head-tail poly(glucaramides)
AssigneeThe University of Montana
InventorsDonald E. Kiely, Kylie Kramer
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Abstract
A method of producing high molecular weight stereoregular head, tail-poly(alkylene D-glucaramides) is described. Amidoamino acids are esterified in cold alcohol and then polymerized in a protic solvent to form steroregular prepolymers. The prepolymers are then further polymerized by dissolving them in a solvent to form larger, purer postpolymers. Compositions of matter prepared using the subject method are also described.
Claims15
A method of producing a stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer, the method comprising the steps of:
- a) esterifying an amidoamino acid in an alcohol, wherein the amidoamino acid is derived from D-glucaric acid and an alkylene diamine, the amide bond between C-6 of the glucaryl unit and one nitrogen from one of the amine units of the alkylene diamine. the amidoamino acid having a single amine unit at the alkylene terminus and a carboxylic acid unit at the C-1, D-glucaryl terminus;
- b) polymerizing the esterified amidoamino acid in a protic solvent in the presence of a tertiary amine to form a stereoregular prepolymer;
- and
- c) polymerizing the stereoregular prepolymer in a solvent that is different from the solvent of step b) to form the stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer.
A stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer produced by a method comprising the steps of:
- a) esterifying an 6-[N-(4′-aminobutyl)]-D-glucaramide in an alcohol;
- b) polymerizing the esterified 6-[N-(4′-aminobutyl)]-D-glucaramide in a protic solvent in the presence of a tertiary amine to form a stereoregular prepolymer;
- and
- c) polymerizing the stereoregular prepolymer in a solvent that is different from the solvent in step b) to form the stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer;
- wherein said stereoregular head,tail-poly(alkylene D-glucaramide) postpolymer has a repeating unit C10H18O6N2, a degree of polymerization of about 30.0, a number average molecular weight of about 7,868 and an estimated weight average molecular weight of about 16,129.
A stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer produced by a method comprising the steps of:
- a) esterifying an 6-[N-(6′-aminohexyl)]-D-glucaramide in an alcohol;
- b) polymerizing the esterified 6-[N-(6′-aminohexyl)]-D-glucaramide in a protic solvent in the presence of a tertiary amine to form a stereoregular prepolymer;
- and
- c) polymerizing the stereoregular prepolymer in a solvent that is different from the solvent in step b) to form the stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer;
- wherein said stereoregular head,tail-poly(alkylene D-glucaramide) postpolymer has a repeating unit C12H22O6N2, a degree of polymerization of about 42.7, a number average molecular weight of about 12,400 and an estimated weight average molecular weight of about 25,410.
A stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer produced by a method comprising the steps of:
- a) esterifying an 6-[N-(12′-aminododecyl)]-D-glucaramide in an alcohol;
- b) polymerizing the esterified 6-[N-(12′-aminododecyl)]-D-glucaramide in a protic solvent in the presence of a tertiary amine to form a stereoregular prepolymer;
- and
- c) polymerizing the stereoregular prepolymer in a solvent that is different from the solvent in step b) to form the stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer;
- wherein said stereoregular head, tail-poly(alkylene D-glucaramide) postpolymer has a repeating unit C18H34,O6N2, a degree of polymerization of about 17.6, a number average molecular weight of about 6,590 and an estimated weight average molecular weight of about 16,477.
Dependencies are inferred from the claim text.