Cure catalyst, composition, electronic device and associated method
View Patent ↗A cure catalyst is provided. The cure catalyst may include a Lewis acid and one or both of a nitrogen-containing molecule or a non-tertiary phosphine. The nitrogen-containing molecule may include a mono amine or a heterocyclic aromatic organic compound. A curable composition may include the cure catalyst. An electronic device may include the curable composition. Methods associated with the foregoing are provided also.
1. A cure catalyst, comprising a Lewis acid which comprises a tri(aryl)borane; and
a nitrogen-containing molecule, wherein the nitrogen containing molecule is one or more of 1-methyl imidazole, 2-methyl imidazole, 1-phenyl imidazole, 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU), 2-ethyl-4-methylimidazole, 2,4-dimethylimidazole, butylimidazole, 2-heptadecenyl-4-methylimidazole, 2-undecenylimidazole, 1-vinyl-2-methylimidazole, 2-phenylimidazole, 2-ethyl 4-methylimidazole, 1-benzyl-2-methylimidazole, 1-propyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-guanaminoethyl-2-methylimidazolearyl substituted imidazole, phenylimidazole, 2,3,5-triphenylimidazole, 2-styrylimidazole, 1-(dodecyl benzyl)-2-methylimidazole, 2-(2-hydroxyl-4-t-butylphenyl)-4,5-diphenylimidazole, 2-(2-methoxyphenyl)-4,5-diphenylimidazole, 2-(3-hydroxyphenyl)-4,5-diphenylimidazole, 2-(p-dimethylaminophenyl)-4,5-diphenylimidazole, 2-(2-hydroxyphenyl)-4,5-diphenylimidazole, di(4,5-diphenyl-2-imidazole)-benzene-1,4,2-naphthyl-4,5-diphenylimidazole, 1-benzyl-2-methylimidazole, 2-p-methoxystyrylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, an addition product of imidazole and trimellitic acid, 1,4-diazabicyclo[2,2,2]octane, and 1,7,10,16-tetraoxa-4,1,3-diazacyclooctadecane.
2. The catalyst as defined in claim 1 , wherein the Lewis acid is a complex or adduct of the nitrogen-containing molecule.
3. The catalyst as defined in claim 1 , wherein the nitrogen-containing molecule comprises one or both of 1,8-diazabicyclo[5,4,0]undec-7-ene or methyl imidazole.
4. The catalyst as defined in claim 1 , wherein the tri(aryl)borane comprises one or more of phenyl, pentafluorophenyl; 2,3,5,6-tetrafluorophenyl; 2,3,4,5-tetrafluorophenyl; 3,4,5-trifluorophen-1-yl; or 4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl.
5. The catalyst as defined in claim 4 , wherein the Lewis acid comprises one or more non-hydrolysable halogen.
6. The catalyst as defined in claim 1 , wherein the Lewis acid has a structure as shown in Formula (I):
BR 3 (I);
wherein each R is independently at each occurrence a monovalent aromatic hydrocarbon radical having from about 6 to about 14 carbon atoms, optionally, the monovalent aromatic hydrocarbon radical has an electron-withdrawing element or group, or is substituted with at least two halogen atoms.
7. The cure catalyst of claim 1 wherein the Lewis acid and nitrogen-containing molecule components are each present in molar amounts of from about 0.5:1 to 0.95:1.
8. A cure catalyst, consisting essentially of a Lewis acid which comprises
a tri(aryl) borane; and
a nitrogen-containing molecule, wherein the nitrogen containing molecule is one or more of 1-methyl imidazole, 2-methyl imidazole, 1-phenyl imidazole, 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU), 2-ethyl-4-methylimidazole, 2,4-dimethylimidazole, butylimidazole, 2-heptadecenyl-4-methyl imidazole, 2-undecenylimidazole, 1-vinyl-2-methylimidazole, 2-phenylimidazole, 2-ethyl 4-methylimidazole, 1-benzyl-2-methylimidazole, 1-propyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-guanaminoethyl-2-methylimidazolearyl substituted imidazole, phenylimidazole, 2,3,5-triphenylimidazole, 2-styrylimidazole, 1-(dodecyl benzyl)-2-methylimidazole, 2-(2-hydroxyl-4-t-butylphenyl)-4,5-diphenylimidazole, 2-(2-methoxyphenyl)-4,5-diphenylimidazole, 2-(3-hydroxyphenyl)-4,5-diphenylimidazole, 2-(p-dimethylaminophenyl)-4,5-diphenylimidazole, 2-(2-hydroxyphenyl)-4,5-diphenylimidazole, di(4,5-diphenyl-2-imidazole)-benzene-1,4,2-naphthyl-4,5-diphenylimidazole, 1-benzyl-2-methylimidazole, 2-p-methoxystyrylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, an addition product of imidazole and trimellitic acid, 1,4-diazabicyclo[2,2,2]octane, and 1,7,10,16-tetraoxa-4,13-diazacyclooctadecane.