Water-insoluble hydrophilic copolymers

• US 4,277,582 A
• Filed: 06/22/1979
• Issued: 07/07/1981
• Est. Priority Date: 03/03/1978
• Status: Expired due to Term

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Mueller, Karl F., Good, William R.
• Primary Examiner(s): Lieberman, Paul
• Application Number:
  US06/051,337
• Time in Patent Office: 746 Days
• Field of Search: 525/421, 525/422, 525/404, 525/411, 525/925, 526/262
• US Class Current: 525/421
• CPC Class Codes: C08G 18/671 Unsaturated compounds having only one group containing active hydrogen takes precedence on groups C08G18/675 - C08G18/69
• CPC Class Codes: C08G 2210/00 Compositions for preparing hydrogels
• CPC Class Codes: C08G 73/124 the unsaturated precursors containing oxygen in the form of ether bonds in the main chain
• CPC Class Codes: C08L 79/085 Unsaturated polyimide precursors
• CPC Class Codes: Y10S 525/925 Polymer from at least one nonethylenic monomer having terminal ethylenic unsaturation other than polyurethanes, polyesters, polyepoxides, aminoplasts, and phenoplasts

Abstract

A water-insoluble hydrophilic gel comprising: (A) about 30 to about 90% of a hydrophilic (a) polymer of identical or different watersoluble mono-olefinic monomers, or (b) copolymer of said watersoluble monomers with 1 to 70% of water-insoluble, identical or different mono-olefinic monomers, which polymer or copolymer is cross-linked with (B) about 10 to about 70% of a terminal diolefinic hydrophobic macromer having a molecular weight from about 400 to about 8000.

Claims

1. 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-insolulbe monomers, with

(B) about 10 to about 70% by weight of said gel of a terminal diolefinic hydrophilic macromer having a molecular weight from about 400 to about 8000, said monomer having the formula ##STR6## wherein R₁ 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.

2. A gel 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.

3. A gel 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.

4. A gel as claimed in claim 1, wherein said water-soluble monomers are acrylic or methacrylic acid esters derived from the alcohol of the formula

5. A gel 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.

6. A gel 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.

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

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

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

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

11. A gel 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.

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

13. A gel 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.

14. A gel as claimed in claim 1, wherein R₁ is a polypropyleneoxide or polytetramethyleneoxide chain with a molecular weight of about 600 to about 4000.

15. A gel as claimed in claim 1 wherein R₁ is a polypropylene oxide chain with a molecular weight of about 2200, and monomers are selected from the group consisting of 2-hydroxyethyl methacrylate, N-vinylpyrrolidone and a mixture of N-vinylpyrrolidone with ethyl acrylate.

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