Coupling of polyorganophosphazenes to carboxylic acid

Claim 2

A carboxylated phosphazene polymer, comprising a phosphazene polymer backbone covalently coupled to a carboxylate-containing compound through a linking group attached at one end to said carboxylate-containing compound by an amide bond formed at a primary aliphatic amino group of said linking group and at the other end of said linking group to a phosphorous of said backbone.

Claim 3

The carboxylated phosphazene polymer of claim 1, wherein said linking group comprises a divalent organic radical of the formula --AL-- or --AM--, wherein A represents --O-- or --NH--, L represents a divalent C 2 -C 12 alkylene group or a divalent C 2 -C 12 alkylene group substituted by a halogen atom or --CN or said alkylene group having a divalent organic functional group of the formula --O--, --COO--, --CONR--, --RC═CR--, --C═C--, ##STR22## or --CO--, in the chain wherein each R independently represents hydrogen or a C 1 -C 4 alkyl group, m is an integer from 0 to 4, and each E independently represents a halogen atom, --NO 2 , --CN, or --R, and M represents a divalent aryl radical of the formula ##STR23## wherein n is 1 or 2, or ##STR24## wherein L 1 is L or --CH 2 --, and A is directly bonded to a phosphorous atom of said backbone, while L or M is bonded to the nitrogen that forms said amide bond through an aliphatic carbon of group L or M.

Claim 4

The carboxylated phosphazene polymer of claim 2, wherein said linking group has the formula ##STR25## wherein A is O or NH; m is an integer from 0 to 4; and each R 1 independently represents an alkyl group containing 1 to 4 carbon atoms, a nitro group, a cyano group, or a halogen atom.

Claim 5

The carboxylated phosphazene polymer of claim 3, wherein said linking group has the formula ##STR26##

Claim 6

The carboxylated phosphazene polymer of claim 4, wherein A is O.

Claim 7

The carboxylated phosphazene polymer of claim 2, wherein organic groups of the formula --QJ are attached to phosphorous atoms of said backbone, wherein Q represent --NR 1 -- wherein R 1 represents hydrogen or methyl, --O--, or a covalent bond and J represents L 1 H, MH, or ##STR27##

Claim 8

The carboxylated phosphazene polymer of claim 6, wherein the ratio of linking groups to organic groups is from 1:100 to 3:1.

Claim 9

The carboxylated phosphazene polymer of claim 7, wherein said ratio is from 1:10 to 1:1.

Claim 10

The carboxylated phosphazene polymer of claim 7, wherein said ratio is about 1:3.

Claim 11

The carboxylated phosphazene polymer of claim 6, wherein said linking group has the formula ##STR28##

Claim 12

The carboxylated phosphazene polymer of claim 10, wherein A is O.

Claim 13

The carboxylated phosphazene polymer of claim 11, wherein the ratio of linking groups to organic groups is from 1:100 to 2:1.

Claim 14

The carboxylated phosphazene polymer of claim 6, wherein said organic groups --QJ impart water solubility to said complex.

Claim 15

The carboxylated phosphazene polymer of claim 13, wherein --QJ represent --N(CH 3 ) 2 or ##STR29## wherein R 2 represents a side chain of a naturally occurring amino acid.

Claim 16

The carboxylated phosphazene polymer of claim 14, wherein R 2 represents hydrogen.

Claim 17

The carboxylated phosphazene polymer of claim 6, wherein said organic groups --QJ impart biodegradability to said complex.

Claim 18

The carboxylated phosphazene polymer of claim 16, wherein --QJ represents ##STR30## wherein R 2 represents a side chain of a naturally occurring amino acid.

Claim 19

The carboxylated phosphazene polymer of claim 6, wherein said organic group --QJ imparts biochemical stability to said complex.

Claim 20

The carboxylated phosphazene polymer of claim 18, wherein --QJ represents ##STR31## or a fluorinated C 2 -C 4 alkoxyl.

Claim 21

The carboxylated phosphazene polymer of claim 19, wherein --QJ represents --OCH 2 CF 3 .

Claim 22

The carboxylated phosphazene polymer of claim 1, wherein said polymeric phosphazene backbone is a cyclic trimer.

Claim 23

The carboxylated phosphazene polymer of claim 1, wherein said polymeric phosphazene backbone is a linear chain containing from 3 to 30,000 ##STR32## repeating units.

Claim 24

The carboxylated phosphazene polymer of claim 22, wherein said backbone contains from 100 to 20,000 repeating units.

Claim 25

The carboxylated phosphazene polymer of claim 23, wherein said backbone contains about 15,000 repeating units.

Claim 26

A phosphazene polymer, comprising a phosphazene polymer backbone covalently coupled to a radical of the formula ##STR33## wherein A is O or NH; m is an integer from 0 to 4; each R 1 independently represents an alkyl group containing 1 to 4 carbon atoms, a nitro group, a cyano group, or a halogen atom; and Y is --CH 2 NH 2 or --CN, wherein A is covalently attached to a phosphorous of said phosphazene polymer backbone.

Claim 27

A phosphazene polymer, comprising a phosphazene polymer backbone covalently coupled to a radical of the formula ##STR33## wherein A is O or NH; m is an integer from 0 to 4; each R 1 independently represents an alkyl group containing 1 to 4 carbon atoms, a nitro group, a cyano group, or a halogen atom; and Y is --CH 2 NH 2 or --CN, wherein A is covalently attached to a phosphorous of said phosphazene polymer backbone.

Claim 28

The phosphazene polymer of claim 25, wherein said radical has the formula ##STR34##

Claim 31

The method of claim 27, wherein said radical has the formula --ALNH 2 or --AMNH 2 , wherein A represents --O-- or --NH--, L represents a divalent C 2 -C 12 alkylene group or a divalent C 2 -C 12 alkylene group substituted by a halogen atom or --CN or said alkylene group having a divalent organic functional group of the formula --O--, --COO--, --CONR--, --RC═CR--, --C═C--, ##STR35## or --CO--, in the chain wherein each R independently represents hydrogen or a C 1 -C 4 alkyl group, m is an integer from 0 to 4, and each E independently represents a halogen atom, --NO 2 , --CN, or --R, and M represents a divalent aryl radical of the formula ##STR36## wherein n is 1 or 2, or ##STR37## wherein L 1 is L or --CH 2 --, and A is directly bonded to a phosphorous atom of said backbone, while L or M is bonded to the nitrogen that forms said amide bond through an aliphatic carbon of group L or M.

Claim 32

The method of claim 27, wherein said radical has the formula ##STR38##

Claim 33

The method of claim 29, wherein m is zero.

Claim 34

The method of claim 29, wherein A is O.

Claim 35

The carboxylated phosphazene polymer of claim 11, wherein QJ represents ##STR39## or a flourinated C 2 -C 4 alkoxyl.