Alkylated fluorochemical oligomers and use thereof

• US 6,288,157 B1
• Filed: 05/11/1999
• Issued: 09/11/2001
• Est. Priority Date: 05/11/1999
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Dams, Rudolf J., Klun, Thomas P., Jariwala, Chetan P., Jones, Marvin E.
• Primary Examiner(s): Cain, Edward J.
• Application Number:
  US09/309,836
• Time in Patent Office: 854 Days
• Field of Search: 526/242, 526/250, 526/253, 526/254, 526/255, 524/462, 524/463
• US Class Current: 524/462
• CPC Class Codes: C07C 323/52 the carbon skeleton being acyclic and saturated
• CPC Class Codes: C14C 9/00 Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
• CPC Class Codes: D06M 13/236 containing halogen atoms
• CPC Class Codes: D06M 13/256 Sulfonated compounds esters thereof, e.g. sultones
• CPC Class Codes: D06M 13/265 containing halogen atoms
• CPC Class Codes: D06M 15/277 containing fluorine
• CPC Class Codes: D06M 15/53 Polyethers polyacetals D06M15/39
• CPC Class Codes: D06M 2200/11 Oleophobic properties
• CPC Class Codes: D06M 2200/12 Hydrophobic properties

Abstract

This invention provides fluorochemical compounds comprising: a fluorochemical oligomeric portion comprising an aliphatic backbone with a plurality of pendant fluoroaliphatic groups, each fluoroaliphatic group having a fully fluorinated terminal group and each independently linked to a carbon atom of the aliphatic backbone through an organic linking group; an aliphatic moiety; and a linking group which links the fluorochemical oligomeric portion to the aliphatic moiety. The fluorochemical compounds are useful as topical treatments for fibrous substrates such as textiles and fabrics, and as polymer melt additives to provide desirable oil-, water and stain repellency to shaped articles such as fibers.

Claims

1. Fluorochemical oligomeric compounds of the formula:

wherein

each L independently comprises a linking group;

R is a linear, monovalent alkyl group of 12 to 75 carbon atoms;

a is an integer such that A is oligomeric and comprises a plurality of R_f groups;

each R₁ is independently a 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;

each Q is a covalent bond or an organic linking group;

R_f is a fluoroaliphatic group;

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

2. The compounds of claim 1 wherein a is 3 to 8.

3. The compounds of claim 2 wherein R_f has the structure C_oF_2o+1, where o is 4to 14.

4. The compounds of claim 1 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.

5. The compounds of claim 4 wherein L is chosen from the group consisting of

6. The compounds of claim 2 comprising oligomerized units of compounds of the formula

wherein R₁, R₂, R_f and Q are as defined in claim 2.

7. A synthetic organic polymer composition comprising one or more compounds of claim 2 and a synthetic organic polymer.

8. The polymer composition of claim 7 wherein the synthetic organic polymer is a thermoplastic polymer.

9. The composition of claim 8 wherein said thermoplastic polymers are selected from the group consisting of polyamides, polyesters, polyurethanes, and polyolefins.

10. The composition of claim 7 wherein said compounds comprises from 0.5 to 5 weight percent of said composition.

11. A shaped article comprising a melt-processible thermoplastic polymer and the compounds of claim 1.

12. The shaped article of claim 11 wherein said compounds provide from 100 to 10,000 ppm fluorine.

13. The shaped article of claim 11 selected from the group of films, sheets and fibers.

14. An oily mist resistant electret filter medium comprising polypropylene electret fibers and the compounds of claim 1.

15. The filter medium of claim 14 wherein said fibers have an effective fiber diameter of 2 to 30 micrometers.

16. The filter medium of claim 14 wherein said fibers have been annealed.

17. The filter medium of claim 14 wherein said filter media has a basis weight of 10 to 100 g/m².

18. The compounds of claim 1 wherein Q is selected from the group consisting of

19. The composition of claim 7 wherein the synthetic organic polymer is a thermoset polymer.

20. The composition of claim 19 wherein said thermoset polymer is selected from the group consisting of epoxy resins, urethanes and acrylates.

21. The compounds of claim 1 wherein R is an alkyl group of 18 to 60 carbon atoms,

a version marked up to show changes made to the claim(s) relative to the previous version of the claim(s) is attached.