Thermally stable biuret and isocyanurate based surface modifying macromolecules and uses thereof

• US 9,751,972 B2
• Filed: 02/24/2014
• Issued: 09/05/2017
• Est. Priority Date: 08/28/2008
• Status: Active Grant

• Current Assignee: Evonik Canada Inc. (Rag-Stiftung)
• Original Assignee: Interface Biologics, Inc.
• Inventors: Mullick, Sanjoy, Chang, Weilun, Piotrowicz, Alexandra, Ho, Jeannette, Witmeyer, Richard
• Primary Examiner(s): Dollinger, Mike M
• Application Number:
  US14/188,441
• Publication Number:
  US 20150025198A1
• Time in Patent Office: 1,289 Days
• Field of Search: 525453, 525460, 528 59, 528 83
• CPC Class Codes: C08G 18/227 of antimony, bismuth or arsenic
• CPC Class Codes: C08G 18/2885 containing halogen atoms
• CPC Class Codes: C08G 18/44 Polycarbonates
• CPC Class Codes: C08G 18/6208 Hydrogenated polymers of conjugated dienes
• CPC Class Codes: C08G 18/714 containing nitrogen in addition to isocyanate or isothiocyanate nitrogen
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/7831 containing biuret groups
• CPC Class Codes: C08G 18/791 containing isocyanurate groups
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08G 18/8087 containing halogen atoms
• CPC Class Codes: C08L 2205/025 containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
• CPC Class Codes: C08L 27/06 Homopolymers or copolymers of vinyl chloride
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 77/00 Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 81/06 Polysulfones; Polyethersulfones
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: Y10T 428/139 Open-ended, self-supporting conduit, cylinder, or tube-type article

Abstract

The invention relates to surface modifying macromolecules (SMMs) having high degradation temperatures and their use in the manufacture of articles made from base polymers which require high temperature processing. The surface modifier is admixed with the base polymer to impart alcohol and water repellency properties.

Claims

1. An admixture comprising a base polymer and a surface modifier of formula (I) or (II):

2. The admixture of claim 1, wherein said surface active group is selected from the group consisting of radicals of the general formula CH_mF_(3-m)(CF₂)_rCH₂CH₂—

and CH_mF_(3-m)(CF₂)_s(CH₂CH₂O)_χ

—

, wherein

m is 0, 1, 2, or 3;

χ

is an integer between 1-10;

r is an integer between 2-20; and

s is an integer between 1-20.

3. The admixture of claim 2, wherein m is 0 or 1.

4. The admixture of claim 2, wherein each surface active group is selected, independently, from the group consisting of (CF₃)(CF₂)₅CH₂CH₂O—

, (CF₃)(CF₂)₇CH₂CH₂O—

, (CF₃)(CF₂)₅CH₂CH₂O—

, CHF₂(CF₂)₃CH₂O—

, and (CF₃)(CF₂)₂CH₂O—

.

5. The admixture of claim 1, wherein A is diethylene glycol-orthophthalic anhydride polyester, and B is formed from isophorone diisocyanate (IPDI) trimer.

6. The admixture of claim 1, wherein A is polytetramethylene oxide, and B is formed from isophorone diisocyanate (IPDI) trimer.

7. The admixture of claim 1, wherein A is poly(diethylene glycol)adipate, and B is formed from isophorone diisocyanate (IPDI) trimer.

8. The admixture of claim 1, wherein A is poly(hexamethylene carbonate), and B is formed from isophorone diisocyanate (IPDI) trimer.

9. The admixture of claim 1, wherein A is poly(ethyleneglycol)-block-poly(propyleneglycol))-block-poly(ethylene glycol), and B is formed from isophorone diisocyanate (IPDI) trimer.

10. The admixture of claim 1, wherein A is hydrogenated polybutadiene, and B is formed from isophorone diisocyanate (IPDI) trimer.

11. The admixture of claim 1, wherein A is hydrogenated polybutadiene, and B is formed from hexamethylene diisocyanate (HDI) trimer.

12. The admixture of claim 1, wherein A is hydrogenated polyisoprene, and B is formed from isophorone diisocyanate (IPDI) trimer.

14. The admixture of claim 1, wherein said base polymer is selected from polypropylenes, polyethylenes, polyesters, polyurethanes, nylons, polysilicones, polystyrene, poly(methyl methacrylates), polyvinylacetates, polycarbonates, polyacrylonitrile-butadiene), polyvinylchloride (PVC), polysulfones, and polyethersulfones, and blends thereof.

15. The admixture of claim 14, wherein said base polymer is selected from polyesters.

16. The admixture of claim 1, wherein said admixture is formed by (i) mixing said base polymer with a surface modifier of claim 1 to form a mixture;

and (ii) heating said mixture above 220°

C.

17. An article comprising the admixture of claim 1.

18. The article of claim 17, wherein said admixture is molded, melt blown, melt spun, or melt extruded.

13. A surface modifier of formula (I) or (II):