Fluorochemical oligomer and use thereof

• US 6,174,964 B1
• Filed: 09/24/1999
• Issued: 01/16/2001
• Est. Priority Date: 09/24/1999
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Klun, Thomas P., Jariwala, Chetan P.
• Primary Examiner(s): Seidleck, James J.
• Assistant Examiner(s): Asinovsky, Olga
• Application Number:
  US09/404,747
• Time in Patent Office: 480 Days
• Field of Search: 525/276, 525/199, 525/200, 526/243, 526/227, 526/232.1, 526/245, 526/253, 524/462, 524/544, 524/560, 428/421, 428/903, 264/10, 264/235, 264/211.22, 264/176.1, 264/210.8, 264/147
• US Class Current: 525/276
• CPC Class Codes: C07C 323/52 the carbon skeleton being acyclic and saturated
• CPC Class Codes: C08K 5/435 Sulfonamides
• CPC Class Codes: C08L 101/00 Compositions of unspecified macromolecular compounds
• CPC Class Codes: C08L 2666/04 Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
• CPC Class Codes: Y10T 428/3154 Of fluorinated addition polymer from unsaturated monomers

Abstract

The present invention provides a novel fluorochemical oligomer, and polymer composition comprising the fluorochemical oligomeric compound and a thermoplastic or thermoset polymer. The polymer composition is useful in preparing shaped articles such as fibers and films which have desirable oil- and water repellency properties.

Claims

1. A fluorochemical oligomeric compound comprising:

(i) an oligomeric portion having both fluoroaliphatic and fluorine-free aliphatic pendent groups;

(ii) an aliphatic moiety; and

(iii) a linking group which links the oligomeric portion to the aliphatic moiety, wherein at least one of said fluorine-free aliphatic pendent groups or said aliphatic moiety has 22 or more carbon atoms.

2. The fluorochemical oligomeric compound of claim 1 wherein the ratio of fluoroaliphatic pendent groups to fluorine-free aliphatic pendent groups is greater than or equal to 4.

3. The fluorochemical oligomer of claim 1 having the structure:

wherein the sum of a+b is an number such that the compound is oligomeric;

R₁ is hydrogen, halogen, or straight chain or branched chain alkyl containing 1 to about 4 carbon atoms;

each R₂ is independently hydrogen or straight chain or branched chain alkyl containing 1 to about 4 carbon atoms;

Q and Q′

are each independently a covalent bond or an organic linking group,

R_f is a fluoroaliphatic group that comprises a fully fluorinated terminal group;

R_h is a fluorine-free aliphatic group; and

X is a hydrogen atom or a group derived from a free radical initiator;

L is a non-polymeric linking group;

wherein at least one of said R_h and R groups has 22 or more carbon atoms.

4. The fluorochemical oligomer of claim 3 wherein the ratio of Rf groups to Rh groups is at least 4:

1.

5. The fluorochemical oligomer of claim 3 wherein R_f has the structure C_oF_2o+1, where o is 4 to 14.

6. The compounds of claim 3 wherein L is selected from the group of a covalent bond, straight chain, branched chain, or cyclic alkylene, arylene, aralkylene, oxy, oxo, hydroxy, thio, sulfonyl, sulfoxy, amino, imino, sulfonamido, carboxamido, carbonyloxy, urethanylene, ureylene, and combinations thereof.

7. The compounds of claim 3 wherein L is chosen from the group consisting of a covalent bond,

8. The compounds of claim 3 comprising oligomerized units of compounds of the formula

9. A polymer composition comprising the fluorochemical oligomeric compound of claim 1 and a thermoplastic or thermoset polymer.

10. The composition of claim 9 wherein said thermoplastic polymers are selected from the group consisting of polyamides, acrylates, polyesters, polyurethanes, and polyolefins.

11. The composition of claim 10 wherein said fluorinated oligomeric compound comprises from 0.5 to 5 weight percent of said composition.

12. A shaped article comprising the composition of claim 10.

13. The shaped article of claim 12 wherein said fluorinated oligomeric compound comprises from 10 to 10,000 ppm fluorine.

14. The shaped article of claim 12 selected from the group of films, sheets and fibers.

15. An oily mist resistant electret filter medium comprising polypropylene electret fibers comprising the composition of claim 9.

16. The filter medium of claim 15 wherein said fibers have an effective fiber diameter of 2 to 30 micrometers.

17. The filter medium of claim 15 wherein said fibers have been annealed.

18. The filter medium of claim 15 wherein said filter media has a basis weight of 10 to 100 g/m².

19. A fabric comprising the fibers of claim 14.

20. A medical gown comprising the fabric of claim 17.

21. The composition of claim 9 wherein said thermoset polymer is selected from the group consiting of polyurethanes, epoxy resins, epoxides and acrylates.