Poly(arylene ether) compositions
View Patent ↗A composition includes at least 15 weight percent of a low intrinsic viscosity, bifunctional poly(arylene ether) and at least 20 weight percent of a nonhalogenated solvent. The bifunctional poly(arylene ether)s are substantially and unexpectedly more soluble than their monofunctional analogs. The compositions are useful as concentrates to add bifunctional poly(arylene ether)s to thermosets.
1. A composition, comprising:
at least 15 weight percent of a bifunctional poly(arylene ether) having an intrinsic viscosity of about 0.03 to 0.12 deciliter per gram measured in chloroform at 25° C.; wherein the bifunctional poly(arylene ether) has the structure
wherein Q 1 and Q 2 are identical within each phenylene ether unit and selected from the group consisting of halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Q 3 and Q 4 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Q 5 and Q 6 is independently selected from the group consisting of halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; x and y are independently 0 to about 30 with the proviso that the sum of x and y is at least 2; and L has the structure
wherein each occurrence of R 1 and R 2 and R 3 and R 4 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; z is 0 or 1; and Y has a structure selected from the group consisting of
wherein each occurrence of R 5 is independently selected from the group consisting of hydrogen and C 1 -C 12 hydrocarbyl, and each occurrence of R 6 and R 7 is independently selected from the group consisting of hydrogen, C 1 -C 12 hydrocarbyl, and C 1 -C 6 hydrocarbylene wherein R 6 and R 7 collectively form a C 4 -C 12 alkylene group; and
at least 20 weight percent of a solvent selected from the group consisting of C 3 -C 8 ketones, C 4 -C 8 N,N-dialkylamides, C 4 -C 16 dialkyl ethers, C 3 -C 6 alkyl alkanoates, C 2 -C 6 alkyl cyanides, and mixtures thereof;
wherein the bifunctional poly(arylene ether) has a solubility in the composition of at least 100 grams per kilogram of composition at 23° C.;
wherein the composition is substantially free of C 1 -C 6 alkanols, alkali metal ions, and metal ions effective for the catalysis of oxidative polymerization of phenols; and
wherein all weight percents are based on the total weight of the composition.
2. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a solubility in the composition of 100 to about 700 grams per kilogram of composition at 23° C.
3. The composition of claim 1 , wherein the bifunctional poly(arylene ether) is soluble in the composition for one day at 23° C.
4. The composition of claim 1 , wherein the bifunctional poly(arylene ether) is soluble in the composition for two days at 23° C.
5. The composition of claim 1 , wherein the bifunctional poly(arylene ether) is soluble in the composition for seven days at 23° C.
6. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a 23° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
7. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a one-day 23° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
8. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a two-day 23° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
9. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a seven-day 23° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
10. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a 2° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
11. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a one-day 2° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
12. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a two-day 2° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
13. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a seven-day 2° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
14. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a −10° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
15. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a one-day −10° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
16. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a two-day −10° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
17. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has a seven-day −10° C. solubility in the solvent of at least 15 weight percent based on the total weight of the bifunctional poly(arylene ether) and the solvent.
18. The composition of claim 1 , having a viscosity less than or equal to 2000 centipoise at 23° C.
19. The composition of claim 1 , comprising about 40 to about 80 weight percent of the bifunctional poly(arylene ether) and about 20 to about 60 weight percent of the solvent.
20. The composition of claim 1 , consisting of about 40 to about 80 weight percent of the bifunctional poly(arylene ether) and about 20 to about 60 weight percent of the solvent.
21. The composition of claim 1 , wherein the bifunctional poly(arylene ether) has the structure
wherein each occurrence of Q 7 and Q 8 is independently methyl or di-n-butylaminomethyl; and each occurrence of a and b is independently 1 to about 20, with the proviso that the sum of a and b is at least 2.
22. The composition of claim 1 , wherein the solvent is a C 3 -C 8 ketone.
23. The composition of claim 1 , wherein the solvent is methyl ethyl ketone.
24. The composition of claim 1 , wherein the solvent is methyl ethyl ketone and the a bifunctional poly(arylene ether) is a copolymer of 2,6-dimethylphenol and 2,2-bis(3,5-dimethyl-4-hydroxyphenol)propane having an intrinsic viscosity of 0.05 to 0.07 deciliter per gram measured in chloroform at 25° C.
25. The composition of claim 1 , wherein the solvent is methyl isobutyl ketone.
26. The composition of claim 1 , wherein the solvent is a C 4 -C 8 N,N-dialkylamide.
27. The composition of claim 1 , wherein the solvent comprises N-methyl-2-pyrrolidone.
28. The composition of claim 1 , wherein the solvent comprises a C 4 -C 16 dialkyl ether.
29. The composition of claim 1 , wherein the solvent is ethylene glycol monomethyl ether.
30. The composition of claim 1 , wherein the solvent comprises a C 3 -C 6 alkyl alkanoate.
31. The composition of claim 1 , wherein the solvent is ethyl acetate.
32. The composition of claim 1 , wherein the solvent comprises a C 2 -C 6 alkyl cyanide.
33. The composition of claim 1 , wherein the solvent is acetonitrile.
34. The composition of claim 1 , wherein the composition is substantially free of any polymer other than a poly(arylene ether).
35. The composition of claim 1 , wherein the composition is substantially free of halide ions.
36. The composition of claim 1 , wherein the composition is substantially free of nitrogen-containing ligands effective for the oxidative polymerization of phenols.
37. The composition of claim 1 , wherein the composition is substantially free of thermoset resin.
38. A composition, consisting of:
15 to about 80 weight percent of a bifunctional poly(arylene ether) having an intrinsic viscosity of about 0.03 to 0.12 deciliter per gram measured in chloroform at 25° C.; wherein the bifunctional poly(arylene ether) has the structure
wherein Q 1 and Q 2 are identical within each phenylene ether unit and selected from the group consisting of halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Q 3 and Q 4 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Q 5 and Q 6 is independently selected from the group consisting of halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; x and y are independently 0 to about 30 with the proviso that the sum of x and y is at least 2; and L has the structure
wherein each occurrence of R 1 and R 2 and R 3 and R 4 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl with the proviso that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; z is 0 or 1; and Y has a structure selected from the group consisting of
wherein each occurrence of R 5 is independently selected from the group consisting of hydrogen and C 1 -C 12 hydrocarbyl, and each occurrence of R 6 and R 7 is independently selected from the group consisting of hydrogen, C 1 -C 12 hydrocarbyl, and C 1 -C 6 hydrocarbylene wherein R 6 and R 7 collectively form a C 4 -C 12 alkylene group; and
about 20 to 85 weight percent of a solvent selected from the group consisting of C 3 -C 8 ketones, C 4 -C 8 N,N-dialkylamides, C 4 -C 16 dialkyl ethers, C 3 -C 6 alkyl alkanoates, C 2 -C 6 alkyl cyanides, and mixtures thereof;
wherein the bifunctional poly(arylene ether) has a solubility in the composition of at least 100 grams per kilogram of composition at 23° C.;
wherein the composition is substantially free of C 1 -C 6 alkanols, alkali metal ions, and metal ions effective for the catalysis of oxidative polymerization of phenols; and
wherein all weight percents are based on the total weight of the composition.
39. A composition, comprising:
about 30 to about 60 weight percent of a bifunctional poly(arylene ether) having an intrinsic viscosity of about 0.03 to about 0.09 deciliter per gram measured in chloroform at 25° C., wherein the bifunctional poly(arylene ether) has the structure
wherein each occurrence of Q 7 and Q 8 is independently methyl or di-n-butylaminomethyl; and each occurrence of a and b is independently 1 to about 20, with the proviso that the sum of a and b is at least 2; and
about 40 to about 70 weight percent of a solvent selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, N,N-dimethylformamide, N-methylpyrrolidone, and mixtures thereof;
wherein the bifunctional poly(arylene ether) is soluble in the composition at 23° C. for seven days; and
wherein all weight percents are based on the total weight of the composition.
40. The composition of claim 39 , wherein the solvent is methyl isobutyl ketone.
41. A composition, consisting of:
about 30 to about 60 weight percent of a bifunctional poly(arylene ether) having an intrinsic viscosity of about 0.03 to about 0.09 deciliter per gram measured in chloroform at 25° C., wherein the bifunctional poly(arylene ether) has the structure
wherein each occurrence of Q 7 and Q 8 is independently methyl or di-n-butylaminomethyl; and each occurrence of a and b is independently 1 to about 20, with the proviso that the sum of a and b is at least 2; and
about 40 to about 70 weight percent of a solvent selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, N,N-dimethylformamide, N-methylpyrrolidone, and mixtures thereof;
wherein the bifunctional poly(arylene ether) is soluble in the composition at 23° C. for seven days; and
wherein all weight percents are based on the total weight of the composition.
42. The composition of claim 41 , wherein the solvent is methyl isobutyl ketone.