Aliphatic diol-based polycarbonates, method of making, and articles formed therefrom

1. A method of making a polycarbonate polymer comprising isosorbide carbonate units, comprising melt reacting

a dihydroxy compound comprising an isosorbide of the general formula (2a):

 and

an activated carbonate,

in the presence of a catalyst consisting essentially of a sodium salt capable of providing a hydroxide ion,

wherein the polycarbonate polymer comprises greater than or equal to 50 mol% isosorbide carbonate units, and wherein the polycarbonate polymer has a Mw of greater than or equal to about 40,000 g/mol as determined by gel-permeation chromatography relative to polystyrene standards.

2. The method of claim 1 , wherein the isosorbide comprises formula (2b), formula (2c), formula (2d) or a combination comprising at least one of the foregoing:

3. The method of claim 1 , wherein the activated carbonate has a formula(16):

wherein Ar is a substituted C 6-30 aromatic group.

4. The method of claim 3 , wherein the activated carbonate has formula (17):

wherein Q 1 and Q 2 are each independently an activating group present on A 1 and A 2 respectively, positioned ortho to the carbonate linkage; A 1 and A 2 are each independently aromatic rings which can be the same or different; “d” and “e” have a value of 0 to a maximum equivalent to the number of replaceable hydrogen groups substituted on the aromatic rings A 1 and A 2 respectively, and the sum “d +e” is greater than or equal to 1; R 1 and R 2 are each independently a C 1-30 aliphatic group, a C 3-30 cycloaliphatic group, a C 5,-30 aromatic group, cyano, nitro or halogen; “b” has a value of 0 to a maximum equivalent to the number of replaceable hydrogen atoms on the aromatic ring A 1 minus “d” and “c” is a whole number from 0 to a maximum equivalent to the number of replaceable hydrogen atoms on the aromatic ring A 2 minus “e”.

5. The method of claim 4 , wherein the activated carbonate source comprises bis (methyl salicyl) carbonate.

6. The method of claim 1 , wherein the catalyst is present in an amount of 0.01 to 30 μmol, per mole of dihydroxy compound.

7. The method of claim 1 , where the sodium salt is sodium hydroxide.

8. The method of claim 1 , where the dihydroxy compound further comprises a dihydroxy compound that is not identical to isosorbide.

9. The method of claim 8 , wherein the dihydroxy compound is a dihydroxy aromatic compound.

10. The method of claim 9 , wherein the dihydroxy aromatic compound comprises a bisphenol of formula (4):

wherein R a and R b each independently represent halogen or C 1-12 alkyl; p and q are each independently integers of 0 to 4, and X a is —O—, —S—, —S(O)—, S(O) 2 —, or one of the groups of formula (5a) or (5b):

wherein R c and R d are each independently hydrogen, C 1-12 alkyl, C 1-12 cycloalkyl, C 7-12 arylalkyl, C 1-12 heteroalkyl, or cyclic C 7-12 heteroarylalkyl, and R e is a divalent C 1-12 hydrocarbon group.

11. The method of claim 10 wherein R c and R d are methyl, and p and q are 0.

12. The method of claim 1 , wherein the method further comprises melt reacting a C 2-13 aliphatic dioic acid or derivative thereof with the isosorbide to form ester units, and wherein the polycarbonate polymer is a polyester-polycarbonate further comprising the ester units.

13. The method of claim 12 , wherein the aliphatic dioic acid is 1, 12-dodecanedioic acid.

14. The method of claim 12 , wherein the isosorbide polycarbonate polymer has a Mw of greater than or equal to 46,000 g/mol as determined by gel-permeation chromatography relative to polystyrene standards.

15. The method of claim 1 , wherein the dihydroxy compound consists essentially of isosorbide.

16. A polycarbonate polymer, comprising carbonate units derived from

a dihydroxy compound comprising an isosorbide of general formula (2a):

 and

an activated carbonate,

wherein the polycarbonate polymer comprises greater than 50 mol% isosorbide-derived carbonate units, and wherein the polycarbonate polymer has a Mw of greater than or equal to about 40,000 g/mol as determined by gel-permeation chromatography relative to polystyrene standards.

17. The polycarbonate polymer of claim 14 , wherein the polycarbonate polymer is a homopolymer consisting essentially of isosorbide-derived carbonate units.

18. The polycarbonate polymer of claim 14 , wherein the polycarbonate polymer further comprises additional carbonate units derived from a dihydroxy compound that is not identical to isosorbide, ester units derived from isosorbide and a C 3-12 aliphatic dioic acid or derivative, or a combination of these.

19. The polycarbonate polymer of claim 16 , wherein the polycarbonate polymer further comprises structural units derived from the activated aromatic carbonate.

20. The composition according to claim 19 , wherein the structural units derived from the activated aromatic carbonate are end groups comprising a residue of bis(methyl salicyl) carbonate.

21. A method of making a polycarbonate copolymer comprising isosorbide carbonate units, comprising melt reacting

a dihydroxy compound comprising an isosorbide of the general formula (2a):

a C 2-13 aliphatic dioic acid or derivative thereof, and

an activated carbonate,

in the presence of a catalyst consisting essentially of a sodium salt capable of providing a hydroxide ion,

wherein the polycarbonate polymer comprises greater than or equal to 50 mol% isosorbide carbonate units, and wherein the polycarbonate polymer has a Mw of greater than or equal to about 46,000 g/mol as determined by gel-permeation chromatography relative to polystyrene standards.

22. A polycarbonate polymer, prepared by the method of claim 1 .

23. A polycarbonate copolymer, prepared by the method of claim 21 .

24. A thermoplastic composition, comprising the polycarbonate polymer of claim 22 and an additive.

25. An article, comprising the polycarbonate polymer of claim 22 .