Hydrophilic silicone-organic copolymer elastomers containing bioactine agent

• US 4,833,218 A
• Filed: 03/06/1987
• Issued: 05/23/1989
• Est. Priority Date: 12/18/1984
• Status: Expired due to Fees

• Current Assignee: Dow, Inc.
• Original Assignee: Dow, Inc.
• Inventors: Lee, Chi-Long
• Primary Examiner(s): BRIGGS SR, WILBERT
• Application Number:
  US07/020,216
• Time in Patent Office: 809 Days
• Field of Search: 525/455, 525/479, 528/26, 528/28, 424/78
• US Class Current: 525/455
• CPC Class Codes: C08F 290/148 Polysiloxanes

Abstract

This invention provides compositions which are curable to hydrophilic, water-absorbing silicone-organic copolymer elastomers via free radical polymerization such as by the use of free radical precursors, ultraviolet light or electron beam radiation. The compositions are mixtures of (A) from 50 to 95 parts by weight of block copolymers containing polydiorganosiloxane segments and polyalkyleneoxy segments which block copolymers contain terminal aliphatically unsaturated groups such as those derived from the reaction of isocyanoethyl methacrylate with terminal free hydroxyl groups present on the polyalkyleneoxy segments and the polyalkyleneoxy segments are ultimately attached to the silicon atoms by means of a linkage formed by reaction with a diisocyanate compound and (B) from 5 to 50 parts by weight of at least one substantially water insoluble aliphatically unsaturated organic monomer which is compatible with (A) such as methyl methacrylate. The cured elastomers, some of which are optically clear, are useful as membranes for gas or fluid separations or for the controlled release of bioactive agents such as insecticides, herbicides, or drugs.

Claims

1. A water-absorbing hydrophilic silicone-organic elastomer for the controlled delivery of a bioactive agent comprising a polymerization product formed from a composition consisting essentially of

(A) from 50 to 95 parts by weight of at least one block copolymer of the formula ##STR15## wherein Z is CH₂ ═

CR"COOR"'"'"'NHCO--, E is ##STR16## Q is a divalent radical obtained by removing the NCO radicals from a diisocyanate selected from the group consisting of aliphatic, cycloaliphatic and aromatic diisocyanates, T is a divalent radical selected from the group consisting of --NR"-- and --O-- wherein said T is attached to a carbon atom on --C_c H_2c -- which is at least the third carbon atom away from the silicon atom to which the --C_c H_2c -- radical is attached, a is an integer of from 4 to 49, inclusive, b is an integer of from 0 to 15, inclusive, c is an integer having a value of 3 or 4, d is an integer of from 0 to 25, inclusive, e is an integer of from 5 to 50 inclusive, d+e is no greater than 50 and e is greater than or equal to d, f is 0 or 1, f'"'"' is 0 or 1, f+f'"'"'+b is at least 2, R is a monovalent hydrocarbon or halohydrocarbon radical of from 1 to 6 inclusive carbon atoms which is free of aliphatic unsaturation, R'"'"' is a methyl or a phenyl radical, R" is an alkyl radical of from 1 to 4 inclusive carbon atoms or hydrogen, and R'"'"'" is a divalent hydrocarbon radical of from 2 to 6 inclusive carbon atoms,

(B) from 5 to 50 parts by weight of at least one substantially water insoluble aliphatically unsaturated organic monomer which is compatible with said (A), and

(C) a bioactive agent

cured by maintaining the composition under free radical polymerization conditions for a sufficient amount of time to obtain said polymerization product, said polymerization product being capable of absorbing at least 3% by weight of water based upon the total weight of said polymerization product before exposure to water.

2. The elastomer as claimed in claim 1 which is suitable for use in contact with a patient'"'"'s body and said bioactive agent is a drug.

7. The elastomer as claimed in claim 1 wherein said bioactive agent is selected from the group consisting of insecticides, larvicides, acaricides, herbicides, fertilizers, and drugs.

10. The elastomer as claimed in claim 2 wherein the drug is a hydrophilic drug.

11. The elastomer as claimed in claim 2 wherein the drug is a human drug.

3. The elastomer as claimed in claim wherein said (B) is at least one monomer of the formula ##STR17## wherein W is selected from the group consisting of --COOR"", --OOCCH₃ and --C₆ H₅ wherein R"" is an alkyl radical of from 1 to 6 inclusive carbon atoms and a is an integer of from 8 to 14, inclusive, d is 0, e is an integer of from 10 to 20, inclusive, R is a methyl, phenyl or 3,3,3-trifluoropropyl radical, T is --NR""-- and Z is CH₂ ═

CR"COO(CH₂)₂ NHCO--.

4. The elastomer as claimed in claim 3 which is suitable for use in contact with a patient'"'"'s body and said bioactive agent is a drug.

8. The elastomer as claimed in claim 3 wherein said bioactive agent is selected from the group consisting of insecticides, larvicides, acaricides, herbicides, fertilizers, and drugs.

12. The elastomer as claimed in claim 4 wherein the drug is a hydrophilic drug.

13. The elastomer as claimed in claim 4 wherein the drug is a human drug.

5. The elastomer as claimed in claim wherein R and R'"'"' are each methyl radicals, b is 0, c is 4, R" is --CH₃ and Q is selected from the group consisting of ##STR18##

6. The elastomer as claimed in claim 5 which is suitable for use in contact with a patient'"'"'s body and said bioactive agent is a drug.

9. The elastomer as claimed in claim 5 wherein said bioactive agent is selected from the group consisting of insecticides, larvicides, acaricides, herbicides, fertilizers, and drugs.

14. The elastomer as claimed in claim 6 wherein the drug is a hydrophilic drug.

15. The elastomer as claimed in claim 6 wherein the drug is a human drug.