Process for Preparing Diaryl Alkylphosphonates and Oligomeric/Polymeric Derivatives Thereof

• US 20080045673A1
• Filed: 08/29/2005
• Published: 02/21/2008
• Est. Priority Date: 08/31/2004
• Status: Active Grant

• Current Assignee: ICL-IP America Inc. (ICL Group Ltd.)
• Original Assignee: ICL-IP America Inc. (ICL Group Ltd.)
• Inventors: Piotrowski, Andrew, Weil, Edward, Levchik, Sergei, Yao, Qiang
• Granted Patent: US 7,541,415 B2
• Time in Patent Office: Days
• US Class Current: 525/538
• CPC Class Codes: C07F 9/4084 Esters with hydroxyaryl compounds

Abstract

A process is provided for the production of diaryl alkyl phosphonate by the reaction of triaryl phosphate with dialkyl alkyl phosphonate in the presence of alkali metal iodide catalyst; and, optionally, the diaryl alkyl phosphonate is reacted in situ with aromatic diol and, optionally, with at least one branching monomer, in the absence of other or further added catalyst to provide oligomeric and/or polymeric phosphonate products.

Claims

1. A process for preparing a diaryl alkylphosphonate which comprises reacting triaryl phosphite with dialkyl alkylphosphonate in the presence of a catalytically effective amount of catalyst of the formula MX_n in which M is an alkali metal or alkaline earth metal, X is iodine or bromine and n is equal to the valence of M, optionally in a closed reactor, to provide the diaryl alkyphosphonate.

2. The process of claim 1 wherein the triaryl phosphite is triphenyl phosphite.

3. The process of claim 1 wherein the dialkyl alkylphosphonate is dimethyl methylphosphonate.

4. The process of claim 1 wherein the triaryl phosphite is triphenyl phosphite and the dialkyl alkylphosphonate is dimethyl methylphosphonate.

5. The process of claim 1 wherein in catalyst MX_n, M is sodium or potassium, X is iodine and n is equal to 1.

6. The process of claim 4 wherein in catalyst MX_n, M is sodium or potassium, X is iodine and n is equal to 1.

7. The process of claim 1 wherein the catalyst is present at from about 0.01 to about 0.5% by weight.

8. The process of claim 1 wherein the catalyst is present at from about 0.02 to about 0.2% by weight.

9. The process of claim 4 wherein the catalyst is present at from about 0.01 to about 0.5% by weight.

10. The process of claim 4 wherein the catalyst is present at from about 0.02 to about 0.2% by weight.

11. The process of claim 5 wherein the catalyst is present at from about 0.01 to about 0.5% by weight.

12. The process of claim 5 wherein the catalyst is present at from about 0.02 to about 0.2% by weight.

13. The process of claim 6 wherein the catalyst is present at from about 0.01 to about 0.5% by weight.

14. The process of claim 6 wherein the catalyst is present at from about 0.02 to about 0.2% by weight.

15. The process for preparing arylene alkylphosphonate oligomer and/or polymer which comprises:

a) reacting triaryl phosphite with dialkyl alkylphosphonate in the presence of a catalytically effective amount of catalyst of the formula MX_n in which M is an alkali metal or alkaline earth metal, X is iodine or bromine and n is equal to the valence of M, optionally, in a closed reactor, to provide diaryl alkylphosphonate; and

,

b) reacting the diaryl alkylphosphonate with aromatic diol and, optionally, at least one branching monomer, in the substantial absence of other or further added catalyst to provide the arylene alkyphosphonate oligomer and/or polymer.

16. The process of claim 15 wherein the diaryl alkylphosphonate of step (a) is reacted without removal of catalyst therefrom with the aromatic diol.

17. The process of claim 15 wherein in step (a) the triaryl phosphate is triphenyl phosphite, the dialkyl alkylphosphonate is dimethyl methylphosphonate, in catalyst MX_n, M is sodium, X is iodine and n is equal to 1, the catalyst is present at from about 0.01 to about 0.5% by weight diaryl akylphosphonate is diphenyl methylphosphonate, and in step (b) the aromatic diol is resorcinol and the arylene alkylphosphonate oligomer and/or polymer is resorcinol methylphosphonate oligomer and/or polymer.

18. The process of claim 17 wherein the diaryl alkylphosphonate of step (a) is reacted without removal of catalyst therefrom with the aromatic diol.

19. The process of claim 15 in which the mole ratio of aromatic diol to diaryl alkyl phosphonate is greater than 1 and the arylene alkylphosphonate oligomer and/or polymer possesses at least one terminal hydroxyl group.

20. The process of claim 16 in which the mole ratio of aromatic diol to diaryl alkyl phosphonate is greater than 1 and the arylene alkylphosphonate oligomer and/or polymer possesses at least one terminal hydroxyl group.

21. The process of claim 17 in which the mole ratio of aromatic diol to diaryl alkyl phosphonate is greater than 1 and the arylene alkylphosphonate oligomer and/or polymer possesses at least one terminal hydroxyl group.

22. The process of claim 18 in which the mole ratio of aromatic diol to diaryl alkyl phosphonate is greater than 1 and the arylene alkylphosphonate oligomer and/or polymer possesses at least one terminal hydroxyl group.

23. The process of claim 19 which further comprises:

c) reacting the hydroxyl-terminated arylene alkylphosphonate oligomer and/or polymer with epoxy resin to provide a prepolymer.

24. The process of claim 20 which further comprises:

c) reacting the hydroxyl-terminated arylene alkylphosphonate oligomer and/or polymer with epoxy resin to provide a prepolymer.

25. The process of claim 21 which further comprises:

c) reacting the hydroxyl-terminated arylene alkylphosphonate oligomer and/or polymer with epoxy resin to provide a prepolymer.

26. The process of claim 22 which further comprises:

c) reacting the hydroxyl-terminated arylene alkylphosphonate oligomer and/or polymer with epoxy resin to provide a prepolymer.

27. The process of claim 15 wherein the arylene alkylphosphonate oligomer and/or polymer has a number average molecular weight of from about 800 to about 5,000.

28. The process of claim 15 wherein the arylene alkylphosphonate oligomer and/or polymer has a number average molecular weight of from about 1,000 to about 2,500.

29. The process of claim 17 wherein the arylene alkylphosphonate oligomer and/or polymer has a number average molecular weight of from about 800 to about 5,000.

30. The process of claim 17 wherein the arylene alkylphosphonate oligomer and/or polymer has a number average molecular weight of from about 1,000 to about 2,500.

31. The process of claim 19 wherein the arylene alkylphosphonate oligomer and/or polymer has a number average molecular weight of from about 800 to about 5,000.

32. The process of claim 19 wherein the arylene alkylphosphonate oligomer and/or polymer has a number average molecular weight of from about 1,000 to about 2,500.

33. The process of claim 21 wherein the arylene alkylphosphonate oligomer and/or polymer has a number average molecular weight of from about 800 to about 5,000.

34. The process of claim 21 wherein the arylene alkylphosphonate oligomer and/or polymer has a number average molecular weight of from about 1,000 to about 2,500.