Branched polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto

• US 6,861,499 B2
• Filed: 02/24/2003
• Issued: 03/01/2005
• Est. Priority Date: 02/24/2003
• Status: Expired due to Term

• Current Assignee: FRX Polymers, Inc.
• Original Assignee: Triton Systems, Inc.
• Inventors: Freitag, Dieter, Rice, Norman, Lusignea, Richard, Vinciguerra, Michael
• Primary Examiner(s): Truong, Duc
• Application Number:
  US10/374,829
• Publication Number:
  US 20040167284A1
• Time in Patent Office: 736 Days
• Field of Search: 528/167, 528/487, 528/561, 528/502.R, 528/503, 528/398, 528/484
• US Class Current: 528/398
• CPC Class Codes: C08G 79/04 Phosphorus linked to oxygen or to oxygen and carbon
• CPC Class Codes: C08L 2666/22 Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
• CPC Class Codes: C08L 67/00 Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 85/02 containing phosphorus

Abstract

Disclosed are branched polyphosphonates produced via a superior transesterification process, and methods related thereto. These branched polyphosphonates exhibit a unique and advantageous combination of properties, such as outstanding fire resistance, improved heat stability, improved toughness, and superior processing characteristics. Also disclosed are polymer compositions that comprise these branched polyphosphonates and at least one other polymer, wherein the resulting polymer compositions exhibit flame retardant properties. Further disclosed are articles of manufacture produced from these polymers, such as fibers, films, coated substrates, moldings, foams, fiber-reinforced articles, or any combination thereof; these articles may be coated with a moisture barrier to enhance their moisture resistance properties.

Claims

1. A method for producing branched polyphosphonates, comprising:

placing a molar excess of a phosphonic acid diaryl ester, one or more bisphenols including 2,2-bis(4-hydroxyphenyl)propane, a branching agent, and a phosphonium catalyst into a reaction vessel;

heating the mixture in the vessel under vacuum to a temperature where phenol beings to distill from the vessel; and

heating the reaction mixture until the evolution of phenol has stopped.

2. A method for producing branched polyphosphonates according to claim 1, wherein the amount of molar excess of phosphonic acid diaryl ester is at least about 2 mole percent.

3. A method for producing branched polyphosphonates according to claim 1, wherein the amount of branching agent is at least 0.001 moles per one mole of bisphenol.

4. A method for producing branched polyphosphonates according to claim 1, wherein the amount of phosphonium catalyst is at least about 0.00004 moles per one mole of bisphenol.

5. A method for producing branched polyphosphonates according to claim 1, wherein the phosphonic acid diaryl ester is represented by the following chemical structure.

6. A method for producing branched polyphosphonates according to claim 1, wherein the other bisphenol is 4,4′

-dihydroxybiphenyl, 1,1,-bis(4-hydroxyphenyl)-3,3-dimethyl-5-methyl cyclohexane, or any combination thereof.

7. A method for producing branched polyphosphonates according to claim 1, wherein the phosphonium catalyst is tetraphenylphosphonium phenolate.

8. A method for producing branched polyphosphonates according to claim 1, wherein the branching agent is 1,1,1-tris(4-hydroxyphenyl)ethane.

9. A composition comprising:

the branched polyphosphonate produced in accordance to the method of claim 1.

10. A composition comprising:

a molar excess of phosphonic acid diaryl ester relative to the amount of 2,2-bis(4-hydroxyphenyl) propane, a branching agent, and a phosphonium catalyst having a substituted or unsubstituted phenolate anion combined in a reaction vessel and heated under reduced pressure to a temperature where phenol distills from a melt in the vessel; and

heating the melt until the viscosity of the melt increases.

11. The composition of claim 10 the phosphonic acid diaryl ester has a purity of less than 98%.

12. The composition of claim 10, wherein the amount of molar excess of phosphonic acid diaryl ester is at least about 2 mole percent.

13. The composition of claim 10, wherein the amount of branching agent is at least 0.001 moles per one mole of bisphenol.

14. The composition of claim 10, wherein the amount of phosphonium catalyst is at least about 0.00004 moles per one mole of bisphenol.

15. The composition of claim 10 blended, mixed, or compounded with another polymer, said composition having a limiting oxygen index of at least 27.

16. The composition of claim 10 further comprising:

one or more polymers chosen from the group consisting of a polycarbonate, polyacrylate, polyacrylonitrile, polyester, polyamide, polystyrene, polyurethane, polyepoxy, poly(acrylonitrile butadiene styrene), polyimide, polyarylate, poly(arylene ether), polyethylene, polypropylene, polyphenylene sulfide, poly(vinyl ester), polyvinyl chloride, bismaleimide polymer, polyanhydride, liquid crystalling polymer, polyether, polyphenylene oxide, cellulose polymer, or any combination these wherein the composition has a limiting oxygen index of at least 27.

17. The composition of claim 10 further comprising polycarbonate.

18. The composition of claim 10 further comprising a solvent, said branched polyphosphonate dissolved in said solvent.

19. A composition comprising:

a molar excess of phosphonic acid diaryl ester relative to the amount of 2,2-bis(4-hydroxyphenyl) propane and another bisphenol, a branching agent, and a phosphonium catalyst having a substituted or unsubstituted phenolate anion combined in a reaction vessel and heated under reduced pressure to a temperature where phenol distills from a melt in the vessel; and

heating the melt until the viscosity of the melt increases.

20. The composition of claim 19 wherein the phosphonic acid diaryl ester has a purity of less than 98%.

21. The composition of claim 19, wherein the amount of molar excess of phosphonic acid diaryl ester is at least about 2 mole percent.

22. The composition of claim 19, wherein the amount of branching agent is at least 0.001 moles per one mole of the amount of bisphenol.

23. The composition of claim 19, wherein the amount of phosphonium catalyst is at least about 0.00004 moles per one mole of bisphenol.

24. The composition of claim 19 blended, mixed, or compounded with another polymer, said composition having a limiting oxygen index of at least 27.

25. The composition of claim 19 further comprising:

one or more polymers chosen from the group consisting of a polycarbonate, polyacrylate, polyacrylonitrile, polyester, polyamide, polystyrene, polyurethane, polyepoxy, poly(acrylonitrile butadiene styrene), polyimide, polyarylate, poly(arylene ether), polyethylene, polypropylene, polyphenylene sulfide, poly(vinyl ester), polyvinyl chloride, bismaleimide polymer, polyanhydride, liquid crystalling polymer, polyether, polyphenylene oxide, cellulose polymer, or any combination these wherein the composition has a limiting oxygen index of at least 27.

26. The composition of claim 19 further comprising polycarbonate.

27. The composition of claim 19 further comprising a solvent, said branched polyphosphonate dissolved in said solvent.