Weatherable polycarbonates comprising oxanilide structural units, method, and articles made therefrom

A polycarbonate comprising structural units derived from bisphenol-A, N,N′-bis[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]-ethanediamide, and a carbonate precursor.

A polycarbonate comprising structural units derived from bisphenol-A, N-[4-[1-(4-hydroxyphenyl)-1-methylphenyl]-N′-1-[2-ethoxyphenyl)-ethanediamide, and a carbonate precursor.

A method for making a polycarbonate comprising structural units derived from at least one dihydric phenol and at least one member selected from the group consisting of an oxanilide-comprising compound, an oxamate-comprising compound, and mixtures thereof, which comprises the step of contacting under reactive conditions at least one dihydric phenol, a carbonate precursor, and at least one member selected from the group consisting of an oxanilide-comprising compound, an oxamate-comprising compound, and mixtures thereof.

A method for making a polycarbonate comprising oxanilide structural units which comprises the step of contacting under reactive conditions bisphenol-A, N,N′-bis[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]-ethanediamide, and a carbonate precursor.

A method for making a polycarbonate comprising oxanilide structural units which comprises the step of contacting under reactive conditions bisphenol-A, N-[4-[1-(4-hydroxyphenyl)-1-methylphenyl]-N′-1-[2-ethoxyphenyl)-ethanediamide, and a carbonate precursor.

A method for making a symmetrical oxanilide-comprising dihydric phenol which comprises the step of contacting an aromatic amine bearing a hydroxy group with a diaryl oxalate or a dialkyl oxalate bearing alkyl groups each substituted with at least one electron-withdrawing group.

A method for making a symmetrical oxanilide-comprising dihydric phenol which comprises the step of contacting an aromatic amine selected from the group consisting of 3-aminophenol, 4-aminophenol, and 2-(4-aminophenyl)-2-(4′-hydroxyphenyl)propane, with bis(trifluoroethyl)oxalate at a temperature in a range of between about 30° C. and about 100° C.

A method for making an unsymmetrical oxanilide-comprising dihydric phenol which comprises the steps of contacting an aromatic amine bearing a hydroxy group with a diaryl oxalate or a dialkyl oxalate bearing alkyl groups each substituted with at least one electron-withdrawing group, followed by contacting the oxamate intermediate with a second aromatic amine bearing a hydroxy group and different from said first aromatic amine.

A method for making an unsymmetrical oxanilide-comprising dihydric phenol which comprises the steps of contacting an aromatic amine bearing a hydroxy group with bis(trifluoroethyl)oxalate, followed by contacting the oxamate intermediate with a second aromatic amine bearing a hydroxy group and different from said first aromatic amine, wherein the aromatic amines are selected from the group consisting of 3-aminophenol, 4-aminophenol, and 2-(4-aminophenyl)-2-(4′-hydroxyphenyl)propane, and in each step the temperature of contacting is in a range of between about 30° C. and about 100° C.

A method for making an oxanilide-comprising monohydric phenol which comprises the steps of contacting an aromatic amine with a diaryl oxalate or a dialkyl oxalate bearing alkyl groups each substituted with at least one electron-withdrawing group, followed by contacting the oxamate intermediate with a second aromatic amine different from said first aromatic amine, wherein only one aromatic amine bears a hydroxy group.

A method for making an oxanilide-comprising monohydric phenol which comprises the steps of contacting an aromatic amine with bis(trifluoroethyl)oxalate, followed by contacting the oxamate intermediate with a second aromatic amine different from said first aromatic amine, wherein only one aromatic amine bears a hydroxy group and wherein the aromatic amines are selected from the group consisting of aniline, phenetidine, 3-aminophenol, 4-aminophenol, and 2-(4-aminophenyl)-2-(4′-hydroxyphenyl)propane, and in each step the temperature of contacting is in a range of between about 30° C. and about 100° C.

A method for making an oxamate-comprising monohydric phenol which comprises the step of contacting an aromatic amine bearing a hydroxy group with a diaryl oxalate or a dialkyl oxalate bearing alkyl groups each substituted with at least one electron-withdrawing group.

A method for making an oxamate-comprising monohydric phenol which comprises the step of contacting an aromatic amine bearing a hydroxy group with bis(trifluoroethyl)oxalate, wherein the aromatic amines are selected from the group consisting of 3-aminophenol, 4-aminophenol, and 2-(4-aminophenyl)-2-(4′-hydroxyphenyl)propane, and in each step the temperature of contacting is in a range of between about 30° C. and about 100° C.

A dialkyl oxalate bearing alkyl groups each substituted with at least one electron-withdrawing group, wherein the electron-withdrawing group is at least one member selected from the group consisting of chloro and fluoro.