Title: Hydrophilic, hydrophobic, and thermoreversible saccharide gels and forms, and methods for producing same
United States Patent: 6,018,033Inventors: Chen; Jun (Hatfield, PA); BongJo; Seong (West Lafayette, IN); Park; Kinam (West Lafayette, IN)
Assignee: Purdue Research Foundation (West Lafayette, IN)Appl. No.: 855588
Filed: May 13, 1997
Polymerizable saccharide monomers are made by the reaction of a saccharose and a (meth)acrylate. Hydrophilic, hydrophobic and thermoreversible gels and foams are formed upon polymerization of the saccharide monomers. Hydrophilic sucrose monomers are synthesized by reaction of sucrose with an epoxy acrylate. Hydrophobic sucrose monomers are synthesized by reaction of sucrose with methacrylol chloride followed by acetyl chloride. Thermoreversible sucrose monomers are obtained by modifying sucrose with polymerizable substituents prepared from methacryloyl chloride and aminocarboxylic acids. The modified sucrose monomers are copolymerized with hydrophobic poly(alkyleneoxide) (meth)acrylates to produce hydrogels exhibiting inverse thermoreversible properties. The thermosensitive hydrogels are biodegradable and can be used in the area of controlled drug delivery.
SUMMARY OF THE INVENTION
The present invention is for novel unsaturated saccharide compounds that are polymerizable to form gels and foams. These saccharide compounds are represented hereinbelow by formulas (I-VII) as follows:
In each of the above formulas, S represents a saccharide
residue, R is hydrogen or a lower alkyl group, e.g., methyl, and n is an
integer from 1 to 8. In formula (II), R' represents an alkyl, aryl or
alkaryl group, and m is an integer from 0 to 7. In formula (III), R"
represents an alkylene, arylene or alkarylene diradical. In formula (IV),
R1 represents a lower alkyl group. In formula (V), R2
represents a lower alkyl group. In formula (VI), R3 is hydrogen
or methyl, and x is an integer from 1 to 10,000. In formula (VII), R4
represents a diradical, which can be an alkylene chain, and aromatic
group, or an alkaryl group, and R5 represents hydrogen or a
lower alkyl group.
Claim 1 of 41 Claims
1. A gel or foam formed by polymerizing a saccharide having a formula selected from formulas (I)-(VII) as follows:
where S is a saccharide residue, R is hydrogen or a lower
alkyl group, and n is an integer from 1 to 8; R' is an alkyl, aryl or
alkaryl group, and m is an integer from 0 to 7; R" is an alkylene,
arylene, or alkarylene diradical; R1 is a lower alkyl group; R2
is a lower alkyl group; R3 is hydrogen or methyl, and x is an
integer from 1 to 10,000; R4 is an alkylene, arylene, or
alkarylene diradical, and R5 is hydrogen or lower alkyl.