Thermoset composition, method for the preparation thereof, and articles prepared therefrom

1. A curable composition, comprising:

a poly(arylene ether); and

a fused alicyclic (meth)acrylate monomer selected from 3α-(meth)acryloyloxyperhydroindene, 3α-(meth)acryloyloxy-7α-hydroxyperhydroindene, 3α,7α-bis[(meth)acryloyloxy]perhydroindene, 4α-(meth)acryloyloxydecalin, 4α,8α-bis[(meth)acryloyloxy]decalin, 4α-(meth)acryloyloxyperhydrofluorene, 4α-(meth)acryloyloxy-9α-hydroxyperhydrofluorene, 4α,9α-bis[(meth)acryloyloxy]perhydrofluorene, 4α-(meth)acryloyloxyperhydroanthracene, 4α-(meth)acryloyloxy-9α-hydroxyperhydroanthracene, 4α,9α-bis[(meth)acryloyloxy]perhydroanthracene, 10α-(meth)acryloyloxyperhydrophenanthrene, 10α-(meth)acryloyloxy-4α-hydroxyperhydrophenanthrene, 4α,10α-bis[(meth)acryloyloxy]perhydrophenanthrene, 2-(meth)acryloyloxytricyclo[5.2.1.0 2,6 ]decane, 2-(meth)acryloyloxy-6-hydroxytricyclo[5.2.1.0 2,6 ]decane, 2,6-bis[(meth)acryloyloxy]tricyclo[5.2.1.0 2,6 ]decane, 2,5-bis[(meth)acryloyloxy]tricyclo[5.2.1.0 2,6 ]decane, 2α-(meth)acryloyloxyperhydroacenaphthene, 2α-(meth)acryloyloxy-8α-hydroxyperhydroacenaphthene, 2α,8α-bis[(meth)acryloyloxy]perhydroacenaphthene, 3α-[(meth)acryloyloxy]perhydroacenaphthene, 3α-(meth)acryloyloxy-9α-hydroxyperhydroacenaphthene, 3α,9α-bis[(meth)acryloyloxy]perhydroacenaphthene, and combinations of the foregoing fused alicyclic (meth)acrylate monomers.

2. The curable composition of claim 1 wherein the poly(arylene ether) comprises repeating structural units having the formula

wherein for each structural unit, each Z 1 is independently halogen, primary or secondary C 1 –C 12 alkyl, C 1 –C 12 aminoalkyl, C 1 –C 12 hydroxyalkyl, phenyl, C 1 –C 12 haloalkyl, C 1 –C 12 hydrocarbyloxy, or C 1 –C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and each Z 2 is independently hydrogen, halogen, primary or secondary C 1 –C 12 alkyl, C 1 –C 12 aminoalkyl, C 1 –C 12 hydroxyalkyl, phenyl, C 1 –C 12 haloalkyl, C 1 –C 12 hydrocarbyloxy, or C 1 –C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms.

3. A curable composition, comprising:

a poly(arylene ether) comprising 2,6-dimethylphenylene ether limits; and

a fused alicyclic (meth)acrylate monomer selected from 3α-(meth)acryloyloxyperhydroindene, 3α-(meth)acryloyloxy-7α-hydroxyperhydroindene, 3α,7α-bis[(meth)acryloyloxy]perhydroindene, 4α-(meth)acryloyloxydecalin, 4α,8α-bis[(meth)acryloyloxy]decalin, 4α-(meth)acryloyloxperhydrofluorene, 4α-(meth)acryloyloxy-9α-hydroxyperhydrofluorene, 4α,9α-bis[(meth)acryloyloxy]perhydrofluorene, 4α-(meth)acryloyloxyperhydroanthracene, 4α-(meth)acryloyloxy-9α-hydroxyperhydroanthracene, 4α,9α-bis[(meth)acryloyloxy]perhydroanthracene, 10α-(meth)acryloyloxyperhydrophenanthrene, 10α-(meth)acryloyloxy-4α-hydroxyperhydrophenanthrene, 4α,10α-bis[(meth)acryloyloxy]perhydrophenanthrene, 2-(meth)acryloyloxytricyclo[5.2.1.0 2,6 ]decane, 2-(meth)acryloyloxy-6-hydroxytricyclo[5.2.1.0 2,6 ]decane, 2,6-bis[(meth)acryloyloxy] tricyclo[5.2.1.0 2,6 ]decane, 2,5-bis[(meth)acryloyloxy]tricyclo[5.2.1.0 2,6 ]decane, 2α-(meth)acryloyloxyperhydroacenaphthene, 2α-(meth)acryloyloxy-8α-hydroxyperhydroacenaphthene, 2α,8α-bis[(meth)acryloyloxy]perhydroacenaphthene, 3α-[(meth)acryloyloxy]perhydroacenaphthene, 3α-(meth)acryloyloxy-9α-hydroxyperhydroacenaphthene, 3α,9α-bis[(meth)acryloyloxy]perhydroacenaphthene, and combinations of the foregoing fused alicyclic (meth)acrylate monomers.

4. A curable composition, comprising:

a poly(arylene ether) comprising 2,6-dimethylphenylene ether units in combination with 2,3,6-trimethyl-1,4-phenylene ether units; and

a fused alicyclic (meth)acrylate monomer selected from 3α-(meth)acryloyloxyperhydroindene, 3α-(meth)acryloyloxy-7α-hydroxyperhydroindene, 3α,7α-bis[(meth)acryloyloxy]perhydroindene, 4α-(meth)acryloyloxydecalin, 4α,8α-bis[(meth)acryloyloxy]decalin, 4α-(meth)acryloyloxyperhydrofluorene, 4α-(meth)acryloyloxy-9α-hydroxyperhydrofluorene, 4α,9α-bis[(meth)acryloyloxy]perhydrofluorene, 4α-(meth)acryloyloxyperhydroanthracene, 4α-(meth)acryloyloxy-9α-hydroxyperhydroanthracene, 4α,9α-bis[(meth)acryloyloxy]perhydroanthracene, 10α-(meth)acryloyloxyperhydrophenanthrene, 10α-(meth)acryloyloxy-4α-hydroxyperhydrophenanthrene, 4α,10α-bis[(meth)acryloyloxy]perhydrophenanthrene, 2-(meth)acryloyloxytricyclo[5.2.1.0 2,6 ]decane, 2-(meth)acryloyloxy-6-hydroxytricyclo[5.2.1.0 2,6 ]decane, 2,6-bis[(meth)acryloyloxy] tricyclo[5.2.1.0 2,6 ]decane, 2,5-bis[(meth)acryloyloxy]tricyclo[5.2.1.0 2,6 ]decane, 2α-(meth)acryloyloxyperhydroacenaphthene, 2α-(meth)acryloyloxy-8α-hydroxyperhydroacenaphthene, 2α,8α-bis[(meth)acryloyloxy]perhydroacenaphthene, 3α-[(meth)acryloyloxy]perhydroacenaphthene, 3α-(meth)acryloyloxy-9α-hydroxyperhydroacenaphthene, 3α,9α-bis[(meth)acryloyloxy]perhydroacenaphthene, and combinations of the foregoing fused alicyclic (meth)acrylate monomers.

5. The curable composition of claim 1 , wherein the poly(arylene ether) has an intrinsic viscosity of about 0.05 to about 0.6 deciliters per gram measured in chloroform at 25° C.

6. The curable composition of claim 1 , comprising about 5 to about 95 parts by weight of the poly(arylene ether) per 100 parts by weight total of the poly(arylene ether) and the fused alicyclic (meth)acrylate monomer.

7. The curable composition of claim 1 , wherein the fused alicyclic acrylate comprises 2-(meth)acryloyloxytricyclo[5.2.1.0 2,6 ]decane, 2-(meth)acryloyloxy-6-hydroxytricyclo[5.2.1.0 2,6 ]decane, 2,6-bis[(meth)acryloyloxy]tricyclo[5.2.1.0 2,6 ]decane, or 2,5-bis[(meth)acryloyloxy]tricyclo[5.2.1.0 2,6 ]decane.

8. The curable composition of claim 1 , wherein the fused alicyclic acrylate comprises 2,6-bis[(meth)acryloyloxy] tricyclo[5.2.1.0 2,6 ]decane, or 2,5-bis[(meth)acryloyloxy]tricyclo[5.2.1.0 2,6 ]decane.

9. The curable composition of claim 1 , comprising about 5 to about 95 parts by weight of the fused alicyclic (meth)acrylate monomer per 100 parts by weight total of the poly(arylene ether) and the fused alicyclic (meth)acrylate monomer.

10. The curable composition of claim 1 , further comprising an alkenyl aromatic monomer.

11. The curable composition of claim 1 , further comprising about 5 to about 80 weight percent of a particulate filler, based on the total weight of the composition.

12. The curable composition of claim 1 , further comprising about 2 to about 80 weight percent of a fibrous filler, based on the total weight of the composition.

13. A curable composition, comprising:

an unfunctionalized poly(arylene ether) consisting of the product of oxidative polymerization of at least one monohydroxyaromatic compound; and

a fused alicyclic (meth)acrylate monomer, wherein the fused alicyclic (meth)acrylate monomer has the formula

 wherein each occurrence of R 18 is independently C 1 –C 12 alkylene or C 1 –C 12 hydroxy-substituted alkylene; each occurrence of R 19 is independently a divalent group selected from C 1 –C 18 hydrocarbylene, oxygen (—O—), sulfur (—S—), carbonyl (—C(═O)—), thiocarbonyl (—C(═S)—), sulfoxyl (—S(═O)—), sulfonyl (—S(═O) 2 —), and amine (—N(R 22 )— wherein R 22 is hydrogen or C 1 –C 18 hydrocarbyl); each occurrence of r is independently 0 to about 12; each occurrence of R 20 and R 21 is independently hydrogen or C 1 –C 12 alkyl; and each occurrence of s is.

14. The curable composition of claim 13 , comprising about 5 to about 95 parts by weight of the poly(arylene ether) and about 5 to about 95 parts by weight of the fused alicyclic (meth)acrylate monomer, based on 100 parts by weight total of the poly(arylene ether) and the fused alicyclic (meth)acrylate monomer.

15. A curable composition, comprising:

an unfunctionalized poly(arylene ether) consisting of the product of oxidative polymerization of at least one monohydroxyaromatic compound; and

a fused alicyclic (meth)acrylate monomer, wherein the fused alicyclic (meth)acrylate monomer has the formula

 wherein each occurrence of R 23 is independently hydrogen or methyl.

16. The curable composition of claim 15 , wherein R 23 is methyl.

17. The curable composition of claim 15 , comprising about 5 to about 95 parts by weight of the poly(arylene ether) and about 5 to about 95 parts by weight of the fused alicyclic (meth)acrylate monomer, based on 100 parts by weight total of the poly(arylene ether) and the fused alicyclic (meth)acrylate monomer.

18. A cured composition, comprising the reaction product of the composition of claim 1 .

19. A cured composition, comprising the reaction product of the composition of claim 13 .

20. A cured composition, comprising the reaction product of the composition of claim 15 .