Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups

• US 7,087,710 B2
• Filed: 06/30/2004
• Issued: 08/08/2006
• Est. Priority Date: 05/14/2001
• Status: Expired due to Term

• Current Assignee: OMNOVA Solutions Incorporated
• Original Assignee: OMNOVA Solutions Incorporated
• Inventors: Woodland, Daniel D., Leising, Jane E., Weinert, Raymond J., Kim, Yongsin, Medsker, Robert E., Thomas, Richard R., Kausch, Charles M.
• Primary Examiner(s): Moore, Margaret G.
• Application Number:
  US10/882,738
• Publication Number:
  US 20040242804A1
• Time in Patent Office: 769 Days
• Field of Search: 528/402
• US Class Current: 528/402
• CPC Class Codes: C08G 65/18 Oxetanes
• CPC Class Codes: C08G 65/226 containing fluorine
• CPC Class Codes: C08L 2205/05 containing polymer components which can react with one another
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 71/02 Polyalkylene oxides

Abstract

A fluorine containing polymer which acts as a wetting, flow or leveling agent, and has at least one polar group. The polymer has at least one pendant or ether side chain containing from about 1 to about 20 carbon atoms with at least 25% of the hydrogen atoms being replaced by fluorine atoms. The fluorinated polymers unexpectedly impart wetting, flow or leveling properties to a variety of coatings while producing little foam.

Claims

1. A block copolymer composition, comprising:

at least one polyfluorooxetane block bonded to a polyether block via an ether linkage,

said polyfluorooxetane block having a repeat unit of the formula

2. A block copolymer composition according to claim 1, wherein said DP is from 2 to about 30, and wherein said polyfluorooxetane block is an oligomer, a polymer, or a copolymer.

3. A block copolymer composition according to claim 2, wherein said R_f contains a minimum of 75 percent of said hydrogen atoms being replaced by F.

4. A block copolymer composition according to claim 3, wherein the number average molecular weight of said polyether block is from about 300 to about 5,000, and wherein said polyfluorooxetane block includes one or more repeat units that derive from tetrahydrofuran.

5. A block copolymer composition according to claim 4, wherein said DP is from about 4 to about 20.

6. A block copolymer composition according to claim 5, wherein n is from 1 to about 3, R is methyl or ethyl, wherein said R_f is from 1 to about 7 carbon atoms and contains a minimum of 95% of said hydrogen atoms being replaced by F.

7. A block copolymer composition according to claim 6, wherein said block copolymer is an AB, or a BAB, or a BA, or an ABA block copolymer, wherein said A block is said polyether block and said B block is said polyfluorooxetane block.

8. A flow, or wetting, or leveling agent, comprising the composition of claim 1.

9. A flow, or wetting, or leveling agent, comprising the composition of claim 3.

10. A flow, or wetting, or leveling agent, comprising the composition of claim 5.

11. A flow, or wetting, or leveling agent, comprising the composition of claim 7.

12. A solution comprising a flow, or leveling, or wetting agent comprising the composition of claim 1.

13. A polymer solution containing a flow, or leveling, or wetting agent comprising the composition of claim 1, wherein the block copolymer is an aqueous soluble, dispersible, or an emulsifiable polymer.

14. A polymeric solution containing a flow, or leveling, or wetting agent comprising the composition of claim 1, wherein the block copolymer is a solvent soluble polymer.

15. A polymeric solution containing a flow, or leveling, or wetting agent comprising the composition of claim 6, wherein the block copolymer is a solvent soluble polymer.

16. A composition comprising:

the reaction product of a polyether initiator and a fluorooxetane monomer having the formula

17. A composition according to claim 16, wherein R_f has from 1 to 7 carbon atoms and a minimum of 90 percent of said hydrogen atoms being replaced by F, and wherein said polyether initiator has a molecular weight of from about 300 to about 5,000.

18. A composition according to claim 17, further including the reaction product of said polyether initiator, said fluoroxetane monomer, and a tetrahydrofuran monomer, and wherein said polyether initiator has 2 reactive hydroxyl end groups.

19. A composition according to claim 18, wherein said reaction product is an AB or a BAB block copolymer wherein said A block derives from said polyether initiator and said B block is derived from said fluorooxetane monomers and said tetrahydrofuran monomer.

20. A composition comprising:

the reaction product of a polyfluorooxetane initiator and an alkylene oxide monomer comprising ethylene oxide, propylene oxide, or mixtures thereof, wherein said polyfluorooxetane initiator is an oligomer, a polymer, or a copolymer having 1 or 2 hydroxyl end groups, and having a repeat unit of the formula

21. A composition according to claim 20, wherein R_f has from 1 to 7 carbon atoms and a minimum of 90 percent of said hydrogen atoms being replaced by F.

22. A composition according to claim 21, wherein said polyfluorooxetane copolymer contains repeat groups derived from tetrahydrofuran, and wherein said polyfluorooxetane initiator has two hydroxyl end groups.

23. A composition according to claim 22, wherein n is 1 to about 3, wherein R is methyl or ethyl, and wherein DP is from about 4 to about 20.

24. A composition according to claim 23, wherein said reaction product is a BA or an ABA block copolymer wherein said A block is a polyether block and said B block is a polyfluorooxetane oligomer, polymer, or copolymer.