Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom

A curable composition, comprising:

• about 1 to about 69 parts by weight of a functionalized poly(arylene ether);
• about 30 to about 98 parts by weight of an alkenyl aromatic monomer;
• and
• about 1 to about 69 parts by weight of an alkoxylated acryloyl monomer;
• wherein the amounts of the functionalized poly(arylene ether), the alkenyl aromatic monomer, and the alkoxylated acryloyl monomer sum to 100 parts by weight;
• and
• wherein the functionalized poly(arylene ether) is a capped poly(arylene ether) or a ring-functionalized poly(arylene ether);
• wherein the capped poly(arylene ether) has the structure
• Q(J—K)y
• wherein Q has the structure
• wherein R1-R4 are each independently hydrogen, halogen, primary or secondary C1-C12 alkyl, C1-C12 alkenyl, C1-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, C1-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• and n is 1 to about 100;
• y is 1;
• J comprises recurring units having the structure
• wherein R1-R4 are each independently selected from the group consisting of hydrogen, halogen, primary or secondary C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, and C2-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• m is 1 to about 200;
• and
• K is a capping group selected from the group consisting of
• wherein R5 is C1-C12 alkyl;
• R6-R8 are each independently selected from the group consisting of hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C6-C18 aryl, C7-C18 alkyl-substituted aryl, C7-C18 aryl-substituted alkyl, C2-C12 alkoxycarbonyl, C7-C18 aryloxycarbonyl, C8-C18 alkyl-substituted aryloxycarbonyl, C8-C18 aryl-substituted alkoxycarbonyl, nitrile, formyl, carboxylate, imidate, and thiocarboxylate;
• R9-R13 are each independently selected from the group consisting of hydrogen, halogen, C1-C12 alkyl, hydroxy, and amino;
• and wherein Y is a divalent group selected from the group consisting of
• wherein R14 and R15 are each independently selected from the group consisting of hydrogen and C1-C12 alkyl.

A curable composition, comprising:

• about 10 to about 50 parts by weight of a methacrylate-capped poly(arylene ether);
• about 40 to about 80 parts by weight of a monofunctional alkenyl aromatic monomer;
• about 5 to about 50 parts by weight of a polyfunctional alkoxylated acryloyl monomer;
• and
• about 1 to about 5 parts by weight of a curing catalyst;
• wherein the methacrylate-capped poly(arylene ether) has the structure
• Q(J—K)y
• wherein Q has the structure
• wherein R1-R4 are each independently hydrogen, halogen, primary or secondary C1-C12 alkyl, C1-C12 alkenyl, C1-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, C1-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• X is hydrogen;
• and n is 1 to about 100;
• y is 1;
• J comprises recurring units having the structure
• wherein R1-R4 are each independently selected from the group consisting of hydrogen, halogen, primary or secondary C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, and C2-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• m is 1 to about 200;
• and
• K is a capping group having the structure
• wherein R6-R8 are each independently selected from the group consisting of hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C6-C18 aryl, C7-C18 alkyl-substituted aryl, C7-C18 aryl-substituted alkyl, C2-C12 alkoxycarbonyl, C2-C18 aryloxycarbonyl, C8-C18 alkyl-substituted aryloxycarbonyl, C8-C18 aryl-substituted alkoxycarbonyl, nitrile, formyl, carboxylate, imidate, and thiocarboxylate;
• and
• wherein the amounts of the capped poly(arylene ether), the monofunctional alkenyl aromatic monomer, the polyfunctional alkoxylated acryloyl monomer, and the curing catalyst are based on 100 total parts by weight for the methacrylate-capped poly(arylene ether), the monofunctional alkenyl aromatic monomer, and the polyfunctional alkoxylated acryloyl monomer.

A curable composition, comprising:

• about 10 to about 40 parts by weight of a methacrylate-capped poly(arylene ether);
• about 40 to about 70 parts by weight of styrene;
• about 10 to about 40 parts by weight of a polyfunctional alkoxylated acryloyl monomer selected from the group consisting of alkoxylated trimethylolpropane tri(meth)acrylate, alkoxylated bisphenol-A di(meth)acrylate, alkoxylated cyclohexanedimethanol di(meth)acrylate, and mixtures thereof;
• and
• about 1 to about 5 parts by weight of a curing catalyst;
• wherein the methacrylate-capped poly(arylene ether) has the structure
• Q(J—K)y
• wherein Q has the structure
• wherein R1-R4 are each independently hydrogen, halogen, primary or secondary C1-C12 alkyl, C1-C12 alkenyl, C1-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, C1-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• X is hydrogen;
• and n is 1 to about 100;
• y is 1;
• J comprises recurring units having the structure
• wherein R1-R4 are each independently selected from the group consisting of hydrogen, halogen, primary or secondary C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, and C2-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• m is 1 to about 200;
• and
• K is a capping group having the structure
• wherein R6-R8 are each independently selected from the group consisting of hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C6-C18 aryl, C7-C18 alkyl-substituted aryl, C7-C18 aryl-substituted alkyl, C2-C12 alkoxycarbonyl, C7-C18 aryloxycarbonyl, C8-C18 alkyl-substituted aryloxycarbonyl, C8-C18 aryl-substituted alkoxycarbonyl, nitrile, formyl, carboxylate, imidate, and thiocarboxylate;
• and
• wherein the amounts of the methacrylate-capped poly(arylene ether), the styrene, the polyfunctional alkoxylated acryloyl monomer, and the curing catalyst are based on 100 total parts by weight for the methacrylate-capped poly(arylene ether), the styrene, and the polyfunctional alkoxylated acryloyl monomer.

A cured composition, comprising the reaction product of:

• a functionalized poly(arylene ether);
• an alkenyl aromatic monomer;
• and
• an alkoxylated acryloyl monomer;
• wherein the functionalized poly(arylene ether) is a capped poly(arylene ether) or a ring-functionalized poly(arylene ether);
• wherein the capped poly(arylene ether) has the structure
• Q(J—K)y
• wherein Q has the structure
• wherein R1-R4 are each independently hydrogen, halogen, primary or secondary C1-C12 alkyl, C1-C12 alkenyl, C1-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, C1-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• X is hydrogen;
• and n is 1 to about 100;
• y is 1;
• J comprises recurring units having the structure
• wherein R1-R4 are each independently selected from the group consisting of hydrogen, halogen, primary or secondary C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, and C2-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• m is 1 to about 200;
• and
• K is a capping group selected from the group consisting of
• wherein R5 is C1-C12 alkyl;
• R6-R8 are each independently selected from the group consisting of hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C6-C18 aryl, C7-C18 alkyl-substituted aryl, C7-C18 aryl-substituted alkyl, C2-C12 alkoxycarbonyl, C7-C18 aryloxycarbonyl, C8-C18 alkyl-substituted aryloxycarbonyl, C8-C18 aryl-substituted alkoxycarbonyl, nitrile, formyl, carboxylate, imidate, and thiocarboxylate;
• R9-R13 are each independently selected from the group consisting of hydrogen, halogen, C1-C12 alkyl, hydroxy, and amino;
• and wherein Y is a divalent group selected from the group consisting of
• wherein R14 and R15 are each independently selected from the group consisting of hydrogen and C1-C12 alkyl.

A method of preparing a curable composition, comprising:

• blending a capped poly(arylene ether), an alkenyl aromatic monomer, and an alkoxylated acryloyl monomer to form an intimate blend;
• wherein the capped poly(arylene ether) has the structure
• Q(J—K)y
• wherein Q has the structure
• wherein R1-R4 are each independently hydrogen, halogen, primary or secondary C1-C12 alkyl, C1-C12 alkenyl, C1-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, C1-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• X is hydrogen;
• and n is 1 to about 100;
• y is 1;
• J comprises recurring units having the structure
• wherein R1-R4 are each independently selected from the group consisting of hydrogen, halogen, primary or secondary C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 aminoalkyl, C1-C12 hydroxyalkyl, phenyl, C1-C12 haloalkyl, C1-C12 hydrocarbonoxy, and C2-C12 halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
• m is 1 to about 200;
• and
• K is a capping group selected from the group consisting of
• wherein R5 is C1-C12 alkyl;
• R6-R8 are each independently selected from the group consisting of hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C6-C18 aryl, C7-C18 alkyl-substituted aryl, C7-C18 aryl-substituted alkyl, C2-C12 alkoxycarbonyl, C7-C18 aryloxycarbonyl, C8-C18 alkyl-substituted aryloxycarbonyl, C8-C18 aryl-substituted alkoxycarbonyl, nitrile, formyl, carboxylate, imidate, and thiocarboxylate;
• R9-R13 are each independently selected from the group consisting of hydrogen, halogen, C1-C12 alkyl, hydroxy, and amino;
• and wherein Y is a divalent group selected from the group consisting of
• wherein R14 and R15 are each independently selected from the group consisting of hydrogen and C1-C12 alkyl.

A curable composition, comprising:

• a functionalized poly(arylene ether);
• an alkenyl aromatic monomer;
• and
• an alkoxylated acryloyl monomer having the structure
• wherein R23 is a C1-C250 organic group having a valence of c;
• each occurrence of R24-R27 is independently hydrogen, C1-C6 alkyl, or C6-C12 aryl;
• each occurrence of b is 3 to about 20;
• each occurrence of R28 is independently hydrogen or methyl;
• and c is 1 to about 10.