Phenylene ether copolymer and compositions comprising same
View Patent ↗A copolymer having the structure (I) wherein Q 1 , Q 2 , Q 3 , Q 4 , m, and n are defined herein. The copolymer can be formed by oxidative copolymerization of 2,4,6-trimethyIresorcinoI with a monohydric phenol. Also describes are a composition comprising the copolymer and a solvent, and a composition comprising the copolymer and a thermosetting resin.
1. A copolymer having the structure
wherein each occurrence of Q 1 and Q 2 is independently selected from the group consisting of halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided 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 provided 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; and m and n are independently 0 to 50, provided that, the sum of m and n is at least 3.
2. The copolymer of claim 1 , wherein the sum of m and n is 3 to 15.
3. The polymer of claim 1 , wherein each occurrence of Q 1 and Q 2 is independently methyl, N,N-diethylaminomethyl, N-ethylaminomethyl, or phenyl; each occurrence of Q 3 is hydrogen; and each occurrence of Q 4 is hydrogen, methyl, or phenyl.
4. The copolymer of claim 1 , wherein each occurrence of Q 1 and Q 2 is independently methyl or N,N-diethylaminomethyl or N-ethylaminomethyl; and each occurrence of Q 3 and Q 4 is hydrogen.
5. The copolymer of claim 1 , wherein m and n are each greater than zero.
6. The copolymer of claim 1 , wherein
the sum of m and n is 3 to 15;
each occurrence of Q 1 and Q 2 is methyl or N,N-diethylaminomethyl or N-ethylaminomethyl; and
each occurrence of Q 3 and Q 4 is hydrogen.
7. A composition comprising:
the copolymer of claim 1 ; and
a solvent selected from the group consisting of C 3 -C 8 ketones, C 3 -C 8 N,N-dialkylamides, C 4 -C 16 dialkyl ethers, C 6 -C 12 aromatic hydrocarbons, C 1 -C 3 chlorinated hydrocarbons, C 3 -C 6 alkyl alkanoates, C 2 -C 6 alkyl cyanides, C 2 -C 6 dialkyl sulfoxides, and mixtures thereof.
8. The composition of claim 7 comprising, based on the total weight of the composition,
10 to 50 weight percent of the copolymer; and
50 to 90 weight percent of the solvent.
9. The composition of claim 7 comprising, based on the total weight of the composition,
10 to 50 weight percent of the copolymer; and
50 to 90 weight percent of the solvent, wherein the solvent is selected from the group consisting of N-methyl-2-pyrrolidone, methyl ethyl ketone, and combinations thereof.
10. A composition comprising:
the copolymer of claim 1 ; and
a thermosetting resin.
11. The composition of claim 10 , wherein the thermosetting resin is selected from the group consisting of epoxy resins, unsaturated polyester resins, polyimide resins, bismaleimide resins, bismaleimide triazine resins, cyanate ester resins, vinyl resins, benzoxazine resins, benzocyclobutene resins, acrylics, alkyds, phenol-formaldehyde resins, novolac resins, resole resins, melamine-formaldehyde resins, urea-formaldehyde resins, unsaturated polyesterimides, and combinations thereof.
12. The composition of claim 10 , wherein the thermosetting resin comprises an epoxy resin.
13. The composition of claim 10 comprising, based on the total weight of the composition,
5 to 80 weight percent of claim 1 ; and
20 to 95 weight percent of the thermosetting resin.
14. The composition of claim 10 comprising, based on the total weight of the composition,
20 to 80 weight percent of the copolymer of claim 1 , wherein the sum of m and n is 3 to 15; each occurrence of Q 1 and Q 2 is methyl or N,N-diethylaminomethyl or M-ethylaminomethyl; and each occurrence of Q 3 and Q 4 is hydrogen; and
20 to 80 weight percent of an epoxy resin.