Block polymer having functional groups at both ends

Details Block polymer having functional groups at both ends Block polymer having functional groups at both ends

1998-02-05

1999-07-27

Seidleck, James J.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

525258, 424 7817, 424 7831, 424 7837, 424501, 528409, C08L 7102, C08G 6532, A61K 31765

Patent

active

059291770

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a block polymer which has functional groups on its both ends, a method for the production thereof and its application to polymeric micelle. More detailedly, this invention discloses a polymer which has functional groups on its both ends while having, in its main chain, a polyethylene oxide chain as a hydrophilic segment and another chain derived from polyester or (meth)acrylic acid derivative as a hydrophobic segment.
In this invention, the term "polymer" includes oligomer.


BACKGROUND ART

A polymeric micelle or nanosphere composed of a hydrophilic/hydrophobic type block polymer wherein a hydrophilic polymer like polyethylene oxide is combined with a hydrophobic polymer at the molecular level is now attracting attention as a carrier for drug delivery or the like. Said polymeric micelle and nanosphere have been prepared from a hydrophilic/hydrophobic type block polymer wherein a hydrophilic polymer is combined with a hydrophobic polymer at the molecular level.
In conventional processes to produce a hydrophilic/hydrophobic type block polymer, however, there is a limitation on the species of terminal functional groups to be introduced, and there have only been proposed block polymers whose functional groups are restricted to methoxy or hydroxyl group. If optional functional groups were successfully introduced onto the micelle surface at an optional proportion, it would become possible to provide a functional polymeric micelle which could be useful for drug delivery to certain organs.
Thus, the object of this invention is to provide a block polymer, which has functional groups on both ends of its main chain, as a polyfunctional polymer which is capable of forming a polymeric micelle.


Disclosure of Invention

The inventors of this invention have found out that there can easily be produced a block polymer which has a protected or non-protected amino group, carboxyl group or mercapto group on one end of molecule and various functional groups on the other end, when an alkylene, phenylene or phenylalkylene derivative having a certain kind of protected amino group, carboxyl group or mercapto group and a hydroxyl group is utilized as a living polymerization initiator and when ethylene oxide and lactide or lactone or (meth)acrylic acid ester are polymerized as monomers, and further when electrophilic agent is made to react if necessary.
They have also confirmed that a block polymer obtained in this manner forms a polymeric micelle which is quite stable in an aqueous solvent.
This invention thus provides a block polymer which has functional groups on both ends of molecule and which is represented by formula (I) below: open-st.Y.paren close-st..sub.n Z (I)
wherein X denotes an alkyl group having 1 to 10 carbon atoms which has one or two substituents selected from the group consisting of amino group blocked with amino-protecting group, carboxyl group blocked with carboxyl-protecting group and mercapto group blocked with mercapto-protecting group, or phenyl or phenyl-alkyl group which has the above-mentioned substituents on benzene ring;
Y denotes a group selected from the group consisting of the following recurring units ##STR1##
wherein R.sup.1 and R.sup.2 independently denote hydrogen atom or alkyl group having 1 to 5 carbon atoms; R.sup.3 denotes hydrogen atom or methyl group; R.sup.4 denotes alkyl group having 1 to 5 carbon atoms which is substituted with hydroxyl group under circumstances; q denotes an integer of 2-5;
Z denotes functional group selected from the group consisting of hydrogen atom, acryloyl group (CH.sub.2 .dbd.CH--CO--), methacryloyl group (CH.sub.2 .dbd.C(CH.sub.3)--CO--), vinylbenzyl group ##STR2## allyl group (CH.sub.2 .dbd.CH--CH.sub.2 --), p-toluenesulfonyl group ##STR3## mercapto group, alkyl group having amino group which is mono- or di-substituted under circumstances with alkyl group having 1 to 5 carbon atoms, alkyl group having carboxyl group or its ester group, alkyl group having acetal group, and halogen atom; and
m and n independently

REFERENCES:
patent: 5008109 (1991-04-01), Tin
patent: 5410016 (1995-04-01), Hubbell et al.
patent: 5449513 (1995-09-01), Yokoyama et al.
patent: 5548035 (1996-08-01), Kim et al.

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