Water-insoluble hydrophilic copolymers used as carriers for medicaments and pesticides

Claim 2

A controlled, sustained release composition comprising (a) a pharmaceutically, insecticidally or herbicidally effective agent in an amount at least sufficient for the total dosage during a treatment period, and (b) a water-insoluble hydrophilic gel comprising the crosslinked copolymerization product of (A) about 30 to about 90% by weight of said gel of (a) a water-soluble monoolefinic monomer, or mixture of said monomers, or (b) a water-soluble monomer, or mixture of said monomers, with 1 to 50% by weight of total monomers of a water-insoluble monoolefinic monomer, or mixture of said water-insoluble monomers, with (B) about 10 to about 70% by weight of said gel of a terminal diolefinic hydrophobic macromer having a molecular weight from about 400 to about 8000, said macromer having the formula ##STR6## wherein R 1 is a polycondensate chain having a molecular weight from about 200 to about 8000, which is the residue of a poly(propylene oxide) or poly(tetramethylene oxide) glycol having ether linkages.

Claim 3

A composition as claimed in claim 1, wherein said water-soluble monomers are (a) acrylic or methacrylic acid, or water-soluble esters, amides or imides thereof, or (b) monoolefinic salts thereof or (c) polymers of a monoolefinic, monocyclic azacyclic monomer.

Claim 4

A composition as claimed in claim 1, wherein said water-soluble monomers are acrylic or methacrylic acid, hydroxyalkyl or dialkylaminoalkyl esters thereof, in which alkyl has 2 to 4 carbon atoms.

Claim 5

A composition as claimed in claim 1, wherein said water-soluble monomers are acrylic or methacrylic acid esters derived from the alcohol of the formula HO--C.sub.m H.sub.2m --O--(CH.sub.2 --CH.sub.2 --O).sub.n --R wherein R is hydrogen or methyl, m is 2 to 5 and n is 1 to 20.

Claim 6

A composition as claimed in claim 1, wherein said water-soluble monomers are amides or imides of acrylic or methacrylic acid, in which the N-substituent is hydroxyalkyl, oxaalkyl or dialkylaminoalkyl, wherein alkyl has 2 to 4 carbon atoms.

Claim 7

A composition as claimed in claim 1, wherein said water-soluble monomers are acrylic acid, methacrylic acid, 2-hydroxyethyl or 2- or 3-hydroxypropyl acrylate or methacrylate, N-vinylpyrrolidone, or tert. amino-methacrylimide.

Claim 8

A composition as claimed in claim 1, wherein said water-soluble monomer is 2-hydroxyethyl methacrylate.

Claim 9

A composition as claimed in claim 1, wherein said water-soluble monomer is N-vinyl-2-pyrrolidone.

Claim 10

A composition as claimed in claim 1, wherein said water-soluble monomers are hydroxyalkyl maleates or fumarates, wherein alkyl has 2 to 4 carbon atoms.

Claim 11

A composition as claimed in claim 1, wherein said water-soluble monomers are hydroxyalkyl vinyl ethers, wherein alkyl has 2 to 4 carbon atoms.

Claim 12

A composition as claimed in claim 1, wherein said water-insoluble monomers are acrylonitrile or an alkyl acrylate or methacrylate, wherein alkyl has up to 18 carbon atoms.

Claim 13

A composition as claimed in claim 1, wherein said water-insoluble monomers are vinyl esters derived from an alkanecarboxylic acid having up to 5 carbon atoms.

Claim 14

A composition as claimed in claim 1, wherein said water-insoluble monomers are styrene or a vinyl alkyl ether, wherein alkyl has up to 5 carbon atoms.

Claim 15

A composition as claimed in claim 1, wherein R 1 is a polypropylene oxide or polytetramethylene oxide chain with a molecular weight of about 600 to about 4000.

Claim 16

A composition as claimed in claim 1, wherein about 15 to about 50% of said macromer is used.

Claim 17

A composition according to claim 1 containing a pharmaceutically effective agent.

Claim 18

A composition according to claim 1 containing a insecticidally effective agent.

Claim 19

A composition according to claim 1 containing a herbicidally effective agent.

Claim 20

A controlled, sustained release composition comprising (a) a pharmaceutically, insecticidally or herbicidally effective agent in an amount at least sufficient for the total dosage during a treatment period, and (b) a water-insoluble hydrophilic gel comprising the crosslinked copolymerization product of (A) about 30 to about 90% by weight of said gel of (a) a water-soluble monoolefinic monomer, or mixture of said monomers, or (b) a water-soluble monomer, or mixture of said monomers, with 1 to 50% by weight of total monomers of a water-insoluble monoolefinic monomer, or mixture of said water-insoluble monomers, with (B) about 10 to about 70% by weight of said gel of a terminal diolefinic hydrophobic macromer having a molecular weight from about 400 to about 8000, said macromer having the formula ##STR7## wherein R 1 is a polycondensate chain having a molecular weight from about 200 to about 8000 and which has ester linkages between hydrocarbon residues; R 2 is hydrogen, methyl or --CH 2 COOR 4 , wherein R 4 is hydrogen or an alkyl group with up to 10 carbon atoms; R 3 is hydrogen or COOR 4 , with the proviso that at least one of R 2 and R 3 is hydrogen; X is oxa, --COO--, or --CONR 5 -- wherein R 5 is hydrogen or alkyl with up to 5 carbon atoms and Y is a direct bond or the radical --R 6 --Z 1 --CO--NH--R 7 --NH--CO--Z 2 --, wherein R 6 is linked to X and represents branched or linear alkylene with up to 7 carbon atoms; Z 1 and Z 2 is oxa or NR 5 and R 7 is the diradical of aliphatic or aromatic diisocyanate, with the proviso that in case X is oxa, Y is different from a direct bond, and R 2 and R 3 are hydrogen.

Claim 21

A controlled, sustained release composition comprising (a) a pharmaceutically, insecticidally or herbicidally effective agent in an amount at least sufficient for the total dosage during a treatment period, and (b) a water-insoluble hydrophilic gel comprising the crosslinked copolymerization product of (A) about 30 to about 90% by weight of said gel of (a) a water-soluble monoolefinic monomer, or mixture of said monomers, or (b) a water-soluble monomer, or mixture of said monomers, with 1 to 50% by weight of total monomers of a water-insoluble monoolefinic monomer, or mixture of said water-insoluble monomers, with (B) about 10 to about 70% by weight of said gel of a terminal diolefinic hydrophobic macromer having a molecular weight from about 400 to about 8000, said macromer having the formula ##STR7## wherein R 1 is a polycondensate chain having a molecular weight from about 200 to about 8000 and which has ester linkages between hydrocarbon residues; R 2 is hydrogen, methyl or --CH 2 COOR 4 , wherein R 4 is hydrogen or an alkyl group with up to 10 carbon atoms; R 3 is hydrogen or COOR 4 , with the proviso that at least one of R 2 and R 3 is hydrogen; X is oxa, --COO--, or --CONR 5 -- wherein R 5 is hydrogen or alkyl with up to 5 carbon atoms and Y is a direct bond or the radical --R 6 --Z 1 --CO--NH--R 7 --NH--CO--Z 2 --, wherein R 6 is linked to X and represents branched or linear alkylene with up to 7 carbon atoms; Z 1 and Z 2 is oxa or NR 5 and R 7 is the diradical of aliphatic or aromatic diisocyanate, with the proviso that in case X is oxa, Y is different from a direct bond, and R 2 and R 3 are hydrogen.

Claim 22

A composition as claimed in claim 19, wherein said water-soluble monomers are (a) acrylic or methacrylic acid, or water-soluble esters, amides or imides thereof, or (b) monoolefinic salts thereof or (c) polymers of a monoolefinic, monocyclic azacyclic monomer.

Claim 23

A composition as claimed in claim 19, wherein said water-soluble monomers are acrylic or methacrylic acid, hydroxyalkyl or dialkylaminoalkyl esters thereof, in which alkyl has 2 to 4 carbon atoms.

Claim 24

A composition as claimed in claim 19, wherein said water-soluble monomers are acrylic or methacrylic acid esters derived from the alcohol of the formula HO--C.sub.m H.sub.2m --O--(CH.sub.2 --CH.sub.2 --O).sub.n --R wherein R is hydrogen or methyl, m is 2 to 5 and n is 1 to 20.

Claim 25

A composition as claimed in claim 19, wherein said water-soluble monomers are amides or imides of acrylic or methacrylic acid, in which the N-substituent is hydroxyalkyl, oxaalkyl or dialkylaminoalkyl, wherein alkyl has 2 to 4 carbon atoms.

Claim 26

A composition as claimed in claim 19, wherein said water-soluble monomers are acrylic acid, methacrylic acid, 2-hydroxyethyl or 2- or 3-hydroxypropyl acrylate or methacrylate, N-vinylpyrrolidone, or tert. amino-methacrylimide.

Claim 27

A composition as claimed in claim 19, wherein said water-soluble monomer is 2-hydroxyethyl methacrylate.

Claim 28

A composition as claimed in claim 19, wherein said water-soluble monomer is N-vinyl-2-pyrrolidone.

Claim 29

A composition as claimed in claim 19, wherein said water-soluble monomers are hydroxyalkyl maleates or fumarates, wherein alkyl has 2 to 4 carbon atoms.

Claim 30

A composition as claimed in claim 19, wherein said water-soluble monomers are hydroxyalkyl vinyl ethers, wherein alkyl has 2 to 4 carbon atoms.

Claim 31

A composition as claimed in claim 19, wherein said water-insoluble monomers are acrylonitrile or an alkyl acrylate or methacrylate, wherein alkyl has up to 18 carbon atoms.

Claim 32

A composition as claimed in claim 19, wherein said water-insoluble monomers are vinyl esters derived from an alkanecarboxylic acid having up to 5 carbon atoms.

Claim 33

A composition as claimed in claim 19, wherein said water-insoluble monomers are styrene or a vinyl alkyl ether, wherein alkyl has up to 5 carbon atoms.

Claim 34

A composition as claimed in claim 19, wherein about 15 to about 50% of said macromer is used.

Claim 35

A composition according to claim 19 containing a pharmaceutically effective agent.

Claim 36

A composition according to claim 19 containing a insectidally effective agent.

Claim 37

A composition according to claim 19 containing a herbicidally effective agent.