Bisphenol polyether oligomers, methods of manufacture, and polycarbonates made therefrom
View Patent ↗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 method of producing an article having low estradiol binding activity, the method comprising:
providing a bisphenol polyether oligomer composition that does not exhibit a half maximal inhibitory concentration (IC50) less than 0.00025M for alpha or beta in vitro estradiol receptors, the 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,
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
manufacturing the article with a polycarbonate composition comprising a polyether polycarbonate having repeating carbonate units derived from the bisphenol polyether oligomer composition.
2. The method of claim 1 , wherein the bisphenol polyether oligomer composition further comprises a bisphenol polyether oligomer of the formula
wherein G is H or
and n is 1 to 10.
3. The method of claim 1 , wherein R 4 is methyl or phenyl, and p, q, j, and t are 0.
4. The method claim 1 , wherein the polyether polycarbonate comprises from 5 to 500 of the repeating carbonate units derived from the bisphenol polyether oligomer composition.
5. The method claim 1 , wherein the polyether polycarbonate has a glass transition temperature of greater than 135° C.
6. The method of claim 1 , wherein the endcap of the polyether polycarbonate is a phenoxy group.
7. The method of claim 1 , wherein the polyether polycarbonate further has
a weight average molecular weight of 3,000 to 80,000 Daltons, as measured by gel permeation chromatography (GPC), using a crosslinked styrene-divinylbenzene column and calibrated to polycarbonate references,
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.
8. The method claim 1 , wherein the polyether polycarbonate is a poly(ester carbonate)
comprising repeating carbonate units derived from the bisphenol polyether oligomer composition and repeating ester units derived from a dicarboxylic acid or a reactive derivative of the dicarboxylic acid.
9. The method claim 8 , wherein the dicarboxylic acid is an isophthalic acid, terephthalic acid, or a combination comprising at least one of the foregoing, and the reactive derivative of the dicarboxylic acid is isophthaloyl dichloride, terephthaloyl dichloride, or a combination comprising at least one of the foregoing.
10. The method of claim 1 , wherein the polycarbonate composition further comprises one or more additives.
11. The method of claim 10 , 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.
12. The method of claim 11 , wherein the additive is a phosphorus compound.
13. The method of claim 11 , wherein the additive is a phosphite.
14. The method of claim 11 , wherein the polycarbonate composition further comprises a second polymer component comprising a non-polyether polycarbonate polymer.
15. The method of claim 14 , 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.