Claims
- 1. A glycoside derivative-containing polymer having at least one of repeated units (I) represented by the formula ##STR15## wherein G--O-- is a saccharide residue having no protective group, R is a hydrogen atom or a methyl group, m is 1 or 2, n is an integer of 1 to 4, and l is an integer of 1 or more provided that l.ltoreq.n.
- 2. A polymer according to claim 1 which is a homopolymer having repeated units (I) or a copolymer having at least two different repeated units (I).
- 3. A polymer according to claim 2 which is a copolymer having repeated units (I) and repeated units copolymerizable therewith.
- 4. A polymer according to claim 3 wherein the copolymerizable repeated units are olefin-type repeated units.
- 5. A polymer according to claim 4 wherein the olefin-type repeated units are those represented by the formula ##STR16## wherein R.sup.2, R.sup.3 and R.sup.4 are the same or different and each represent a hydrogen atom or a methyl group, and R.sup.5 is a group ##STR17## (wherein R.sup.6 is a hydrogen atom, an alkyl group, a hydroxyalkyl group, a cycloalkyl group, an aminoalkyl group, a dialkylaminoalkyl group, a glycidyl group, a tetrahydrofuranyl group, a benzyl group, a group --(CH.sub.2 CH.sub.2 O).sub.a CH.sub.2 CH.sub.2 OH (wherein a is an integer of 1 to 10), a group ##STR18## (wherein R.sup.7 is a hydrogen atom or a lower alkyl group, provided that two groups R.sup.7 are the same or different), a cyano group, a hydroxy group, a group ##STR19## (wherein R.sup.8 is a lower alkyl group), a phenyl group which may have at least one substituent selected from the group consisting of chlorine atom, lower alkyl group, cyano group, amino group, hydroxy group and lower alkoxy group, a pyridyl group optionally substituted with a lower alkyl group, a 2-oxypyrrolyl group optionally substituted with an alkyl group, or a carbazole group.
- 6. A polymer according to claim 3 wherein the copolymer has 1 to 99 mole % of repeated units (I) and 99 to 1 mole % of repeated units copolymerizable therewith.
- 7. A material compatible with blood which contains the glycoside derivative-containing polymer of claim 1.
- 8. A non-fogging drip-proof composition which contains the glycoside derivative-containing polymer of claim 1.
Priority Claims (2)
| Number |
Date |
Country |
Kind |
| 63-272168 |
Oct 1988 |
JPX |
|
| 63-332116 |
Dec 1988 |
JPX |
|
DISCLOSURE OF THE INVENTION
This is a division of application Ser. No. 07/499,459 filed Jun 26, 1990, which is now pending.
1. Field of the Invention
The present invention relates to glycoside derivatives, polymers containing the glycoside derivatives, a process for their preparation and the use of said polymers.
2. Prior Art
Polymers having saccharide residues at side chains are increasingly used for various applications utilizing their hydrophilic property and compatibility with organisms, for example, as medical materials including those compatible with blood, surface-treating agents, etc.
The heretofore proposed polymers having saccharide residues at side chains are generally classified into the following two types.
(i) Polymers having saccharide residues obtained by the reaction of known polymers with sugar derivatives.
For example, Japanese Unexamined Patent Publications No. 106802/1985 and No. 192704/1985 disclose the preparation of such polymers by reacting a hydroxymethylated polystyrene with a sugar having hydroxyl groups protected with protective groups such as acetyl groups, halogen atoms or the like, followed by saponification of protective groups of the sugar with an alkali. These polymers, however, have a poor hydrophilic property and a low compatibility with organisms because the protective groups on saccharide residues are not completely removed and the saccharide residues are not uniformly added to the polymers. Further this process can not regulate as desired the amount of the sugar to be added and entails difficulties in removing the reagent used and purifying the polymer thus formed.
(ii) Polymers formed by reacting a vinyl monomer with a saccharide having hydroxyl groups protected with protective groups such as acetyl groups, isopropylidene groups or the like and removing the protective groups after polymerization
For example, U.S. Pat. No. 3,225,012 discloses a polymer represented by the formula ##STR2## the polymer being one prepared by polymerizing 1,2: 5,6-di-O-isopropylidene-3-O-methacryloy-D-glucose and removing the isopropylidene groups from the glucose by acid hydrolysis.
U.S. Pat. No. 3,356,652 describes a polymer having structural units represented by the formula ##STR3##
As further example, Japanese Examined Patent Publication No. 42641/1982 discloses a homopolymer represented by the formula ##STR4## wherein R is a hydrogen atom or a methyl group, R' is a sugar residue attached with the acyl linkage at the 1- position and n is 10 to 1000, the homopolymer being one formed from a monomer which is a sugar derivative having a monosaccharide or disaccharide and an acrylate or methacrylate directly attached to each other with the glycoside linkage.
These publications set forth techniques intended to remove the protective groups with an alkali or acid from the hydroxyl groups of the sugar in the obtained polymer. However, the currently available art can not completely remove the protective groups in polymers. Actually U.S. Pat. No. 3,356,652 teaches that it is impossible to completely remove the acetyl groups in a copolymer containing a hydrophobic monomer. Thus the obtained polymer contains a substantial number of protected hydroxyl groups and is unsatisfactory in hydrophilic property and compatibility with organisms. The treatment of polymers with an alkali or acid impairs the properties of the resulting polymer. Moreover such methods necessitate the neutralization of alkali or acid after removal of protective groups from hydroxyl groups and the washing by water of the salt resulting from neutralization for elimination. The removal of protective groups renders the polymer hydrophilic to give an aqueous viscous solution or water-swollen gel, resulting in incomplete neutralization and desalting. Consequently the polymers formed by the methods are not suitable for use as medical materials.
As described above, polymers with saccharide residues at side chains having no protective group have not been heretofore obtained.
It is an object of the present invention to provide a monomeric compound useful for synthesis of a polymer having as side chains saccharide residues free of the protective group and a process for preparing the same.
It is another object of the invention to provide a polymer having as side chains saccharide residues free of the protective group and a process for preparing the same.
According to the invention, there are provided glycoside derivatives, a polymer containing said glycoside derivatives and a process for their preparation, as described below.
(1) A glycoside derivative represented by the formula ##STR5## wherein G--O-- is a sugar residue free of the protective group, R is a hydrogen atom or a methyl group, m is 1 or 2, n is an integer of 1 to 4, and l is an integer of 1 or more provided that l .ltoreq. n.
The glycoside derivative (1) is a novel compound undisclosed in literature and useful as a monomer for synthesis of a polymer with sugar residues at side chains having no protective group.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
| 3989656 |
Kamiya et al. |
Nov 1976 |
|
Foreign Referenced Citations (1)
| Number |
Date |
Country |
| 59-45306 |
Mar 1984 |
JPX |
Divisions (1)
|
Number |
Date |
Country |
| Parent |
499459 |
Jun 1990 |
|
Patent Grant
5173554
