Allylated amide compounds and die attach adhesives prepared therefrom

A curable composition comprising a curing initiator and an allylated amide compound having the formula

• in which m is 0 or 1, n is 1 to 6, and
• (a) R9 is H, an alkyl group having 1 to 18 carbon atoms, an alkyleneoxy group having 1 to 18 carbon atoms, an allyl group, an aryl group, or a substituted aryl group having the structure
• in which R10, R11, and R12 are independently H or an alkyl or alkyleneoxy group having 1 to 18 carbon atoms;
• (b) X is an aromatic group selected from the group of aromatic groups having the structures:
• (c) Q is selected from the group consisting of
• in which each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms;
• R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents;
• X is O, S, N, or P;
• and v is 0 to 50;
• —(CR12)e—[SiR42—O]f—SiR42—(CR12)g— (ii)
• in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50;
• in which R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents;
• in which p is 1 to 100, each R3 is independently an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents, or each R3 is a siloxane having the structure —(CR12)e—[SiR42—O]f—SiR42—(CR12)g—, in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50;
• and
• in which p is 1 to 100, each R3 independently is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents, or each R3 is a siloxane having the structure —(CR12)e—[SiR42—O]f—SiR42—(CR12)g— in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50;
• (d) K is an aromatic group selected from group of aromatic groups having the structures:
• in which p is 1 to 100;
• in which p is 1 to 100;
• in which R5, R6, and R7 are a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species having up to about 100 atoms in the chain, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the backbone in the chain, and in which any heteratom present may or may not be directly attached to the aromatic ring;
• or
• R5, R6, and R7 are a siloxane having the structure —(CR12)e—[SiR42—O]f—SiR42—(CH3)g— in which the R1 substituent is H or an alkyl group having 1 to 5 carbon atoms and the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, and e is 1 to 10 and f is 1 to 50;
• and
• and
• (e) Z is selected from the group consisting of
• (i)
• in which each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms;
• R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents;
• X is O, S, N, or P;
• and v is 0 to 50;
• —(CR12)e—[SiR42—O]f—SiR 42—(CR12)g— (ii)
• in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is I to 50;
• in which R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents;
• in which p is 1 to 100, each R3 is independently an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents, or each R3 is a siloxane having the structure —(CR12)e—[SiR42—O]f—SiR42—(CR12)g— in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50, and
• in which p is 1 to 100, each R3 independently is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents, or each R3 is a siloxane having the structure —(CR12)e—[SiR42—O]f—SiR42—(CR12)g— in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.