BISPHENOL POLYETHER OLIGOMERS, METHODS OF MANUFACTURE, AND POLYCARBONATES MADE THEREFROM
A bisphenol polyether oligomer composition comprising greater than 90 wt. % of an oligomer of the formula wherein R a , R b , and R c are each independently a C 1-12 alkyl, C 1-12 alkoxy, or C 1-12 alkylarylene, each X a is independently a single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, or a C 1-18 organic group, G is H or p, q, and t are each independently integers of 0 to 4, n is 1 to 10; and wherein the bisphenol polyether oligomer composition comprises: a total halide content of less than 1000 ppm, less than 1000 ppm of —CH 2 OH groups, less than 5 wt. % cyclic oligomers, and less than 100 ppm of a bisphenol of the formula wherein R a , R b , X a , p and q are the same as in the oligomer.
1 . A bisphenol polyether oligomer composition comprising greater than 90 wt. % of an oligomer of the formula
wherein
R a , R b , and R c are each independently a C 1-12 alkyl, C 1-12 alkoxy, or C 1-12 alkylarylene,
each X a is independently a single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, or a C 1-18 organic group,
G is H or
p, q, and t are each independently integers of 0 to 4,
n is 1 to 10; and
wherein the bisphenol polyether oligomer composition comprises:
a total halide content of less than 1000 ppm,
less than 1000 ppm of —CH 2 OH groups,
less than 5 wt. % cyclic oligomers, and
less than 100 ppm of a bisphenol of the formula
wherein R a , R b , X a , p and q are the same as in the oligomer.
2 . The bisphenol polyether oligomer composition of claim 1 , wherein the composition does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors.
3 . The bisphenol polyether oligomer composition of claim 1 , wherein the oligomer is of the formula
wherein G is H or
and the bisphenol is bisphenol A.
4 . The bisphenol polyether oligomer composition of claim 1 , wherein the oligomer is a phthalimidine oligomer of the formula
wherein
R a , R b , and R c are each independently a C 1-12 alkyl, C 1-12 alkoxy, or C 1-12 alkylarylene,
R 3 is each independently a C 1-6 alkyl,
R 4 is hydrogen, C 1-6 alkyl, or a substituted or unsubstituted phenyl,
p, q, j, and t are each independently integers of 0 to 4, and
n is 1 to 10; and
wherein the bisphenol is of the formula
wherein R a , R b , R 3 , R 4 , p, q, and j are the same as defined for the phthalimidine oligomer.
5 . The bisphenol polyether oligomer composition of claim 4 , wherein R 4 is methyl or phenyl, and p, q, j, and t are 0.
6 . The bisphenol polyether oligomer composition of claim 1 , wherein the oligomer is a bisphenol A-phthalimidine polyether oligomer of the formula
wherein
R a , R b , and R c are each independently a C 1-12 alkyl, C 1-12 alkoxy, or C 1-12 alkylarylene,
R 3 is each independently a C 1-6 alkyl,
R 4 is hydrogen, C 1-6 alkyl, or a substituted or unsubstituted phenyl,
p, q, j, and t are each independently integers of 0 to 4,
α is 1 to 10 and β is 1 to 10, provided that α+β is 2 to 10,
G is H or
and
A is
and
wherein the bisphenol is bisphenol A, a bisphenol of the formula (3b)
wherein R a , R b , R 3 , R 4 , p, q, and j are the same as defined for the bisphenol A-phthalimidine polyether oligomer, or a combination of bisphenol A and a bisphenol of formula (3b).
7 . A polyether polycarbonate comprising repeating carbonate unit of the formula
wherein
R a , R b , and R c are each independently a C 1-18 alkyl, C 1-18 alkoxy or alkylarylene,
each occurrence of X a is independently single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, or a C 1-18 organic group,
p, q, and t are each independently integers of 0 to 4; and
n is 1 to 10.
8 . The polyether polycarbonate of claim 7 , comprising from 5 to 500 of polycarbonate repeat units.
9 . The polyether polycarbonate of claim 7 , wherein each thermolytic and hydrolytic degradation product of each of the repeating carbonate units in the polycarbonate does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors.
10 . The polyether polycarbonate of claim 7 , wherein the polycarbonate has a glass transition temperature of greater than 135° C.
11 . The polyether polycarbonate of claim 7 , wherein the endcap is a phenoxy group.
12 . The polyether polycarbonate of claim 7 , further having
an Mw of 3,000 to 80,000 Daltons,
a phenolic end group content less than 20 meq/kg,
a total chloride content less than 50 ppm,
a transition metal content less than 50 ppm, and
a residual phenolic monomer content less than 100 ppm.
13 . The polyether polycarbonate of claim 7 , wherein the repeating carbonate units are of the formula
wherein n is 1 to 10;
wherein n is 1 to 10;
wherein n is 1 to 10;
wherein R 4 is phenyl or methyl and n is 1 to 10;
wherein a is 1 to 10 and β is 1 to 10, provided that α+β is 2 to 10, and A is
or a combination comprising at least one of the foregoing repeating carbonate units.
14 . The polyether polycarbonate of claim 7 , wherein
the polycarbonate is a poly(ester carbonate) further comprising repeating ester units derived from a dicarboxylic acid monomer, and
the dicarboxylic acid monomer does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors.
15 . The polyether polycarbonate of claim 14 , wherein the dicarboxylic acid monomer is a isophthalic acid, terephthalic acid, a C 6-36 aliphatic dicarboxylic acid, a hydroxy benzoic acid, or a combination comprising at least one of the foregoing.
16 . A polyether polycarbonate composition comprising the polyether polycarbonate of claim 7 , and further comprising one or more additives, wherein each additive does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors.
17 . The polyether polycarbonate of claim 16 , wherein the additive is a stabilizer, antioxidant, colorant, impact modifier, flame retardant, anti-drip additive, mold release additive, lubricant, plasticizer, mineral, reinforcement additive, or a combination comprising at least one of the foregoing.
18 . The polyether polycarbonate of claim 16 , wherein the additive is a phosphorus compound, wherein each hydrolysis product of the phosphorous compound does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors.
19 . The polyether polycarbonate of claim 16 , wherein the additive is a phosphite, wherein each hydrolysis product of the phosphite is does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors.
20 . The polyether polycarbonate composition of claim 16 , further comprising a second polymer component comprising a non-polyether polycarbonate polymer.
21 . The polymer composition of claim 20 , wherein the second polymer component comprises a polycarbonate, polyester, polyolefin, polyetherimide, styrene-acrylonitrile, acrylonitrile-butadiene-styrene, methyl methacrylate, methyl methacrylate-butadiene-styrene, styrene-maleic anhydride, styrene-butadiene-styrene, styrene-ethylene-butylene-styrene, polystyrene, or a combination comprising at least one of the foregoing.
22 . An article comprising the polyether polycarbonate composition of claim 16 .
23 . A method of manufacture of an article comprises molding, extruding, or shaping the polyether polycarbonate composition of claim 16 into an article.