Isosorbide-based polycarbonates, method of making, and articles formed therefrom

1. A polycarbonate polymer comprising:

an isosorbide unit,

an aliphatic unit derived from a C 14-44 aliphatic diacid, C 14-44 aliphatic diol, or combination of these; and

optionally, an additional unit different from the isosorbide and aliphatic units,

wherein the isosorbide unit, aliphatic unit, and additional unit are each carbonate, or a combination of carbonate and ester units.

2. The polycarbonate polymer of claim 1 , wherein the isosorbide unit is derived from an isosorbide of formula (2a):

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

4. The polycarbonate polymer of claim 1 , wherein the weight % of the aliphatic unit is between 14 and 22 wt % based on the total weight of the polycarbonate polymer.

5. The polycarbonate polymer of claim 4 , wherein the polycarbonate polymer is a polyester-polycarbonate copolymer comprising C 14-44 aliphatic diacid of formula (11):

where m and m′ are independently 0 to 38, n and n′ are independently 0 to 38, and the sum m+m′+n+n′ is an integer from 8 to 38.

6. The polycarbonate polymer of claim 5 , wherein the aliphatic diacid is a C 36 aliphatic diacid of formula (11), where m and m′ are independently 0 to 30, n and n′ are independently 0 to 30, and the sum m+m′+n+n′ is 30.

7. The polycarbonate polymer of claim 4 , wherein the polycarbonate polymer is a polycarbonate copolymer comprising a C 14-44 aliphatic diol of formula (12):

where t and t′ are independently 0 to 38, u and u′ are independently 0 to 38, and the sum t+t′+u+u′ is an integer from 8 to 38.

8. The polycarbonate polymer of claim 7 , wherein a C 36 aliphatic diol has the structure of formula (12), where t and t′ are independently 0 to 30, u and u′ are independently 0 to 30, and the sum t+t′+u+u′ is 30.

9. The polycarbonate polymer of claim 4 , wherein the isosorbide-based polycarbonate is a polyester-polycarbonate comprising isosorbide units, and both carbonate units and ester units derived from a combination of the C 14-44 aliphatic diacid and the C 14-44 aliphatic diol.

10. The polycarbonate polymer of claim 1 , wherein the additional unit is derived from a dihydroxy aromatic compound.

11. The polycarbonate polymer of claim 10 , 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; or

a dihydroxy aromatic compound of formula (8):

wherein each R f is independently C 1-2 alkyl, or halogen, and u is 0 to 4, or

a combination of a bisphenol of formula (4) and a dihydroxy aromatic compound of formula (8).

12. The polycarbonate polymer of claim 11 , wherein the bisphenol of formula (4) comprises bridging groups X a of formula (5a), where R c and R d are methyl, and p and q are 0.

13. The polycarbonate polymer of claim 1 , wherein the polycarbonate polymer has a molecular weight of greater than or equal to 39,000 g/mol as measured by gel permeation chromatography relative to polystyrene standards.

14. The polycarbonate polymer of claim 12 , wherein the polycarbonate polymer has a glass transition temperature of less than or equal to 135° C.

15. The polycarbonate polymer of claim 1 , wherein the polycarbonate polymer comprises a structural endgroup derived from the activated aromatic carbonate, where the activated aromatic carbonate is bis(methyl salicyl)carbonate.

16. The polycarbonate polymer of claim 15 , wherein the amount of structural endgroup is less than 2,000 ppm based on the weight of the polycarbonate polymer.

17. A polycarbonate polymer comprising:

a) 55 to 97.5 mol % of an isosorbide unit;

b) 2.5 to 15 mol % of an aliphatic unit; and

c) 0 to 42.5 mol % of an additional unit different from the isosorbide and aliphatic units;

wherein the isosorbide unit, aliphatic unit, and additional unit are carbonate units, or a combination of carbonate and ester units, the sum of the number of mol % of isosorbide units, aliphatic units, and carbonate units equals 100 mol %,

wherein the molecular weight of the copolymer is greater than about 39,000 g/mol as measured by gel permeation chromatography relative to polystyrene standards, and wherein the weight percent of aliphatic unit is between 14 and 22 wt % based on the total weight of the polycarbonate polymer.

18. The polycarbonate polymer of claim 17 , wherein the isosorbide units comprise carbonate groups of the formula (2):

19. The polycarbonate polymer of claim 17 , wherein the isosorbide unit or aliphatic unit comprises ester units of formula (11a):

wherein m and m′ are independently 0 to 38, n and n′ are independently 0 to 38, and the sum m+m′n+n′ is an integer from 8 to 38, and z is an integer of greater than or equal to 1.

20. The polycarbonate polymer of claim 17 , wherein the aliphatic units comprise a carbonate unit of formula (12a):

where t and t′ are independently 0 to 38, u and u′ are independently 0 to 38, the sum t+t′+u+u′ is an integer from 8 to 38, and w is an integer of greater than or equal to 1.

21. The polycarbonate polymer of claim 17 , wherein the aliphatic units comprise ester units of formula (14):

wherein m and m′ are independently 0 to 38, n and n′ are independently 0 to 38, and the sum m+m′+n+n′ is an integer from 8 to 38; where t and t′ are independently 0 to 38, u and u′ are independently 0 to 38, the sum t+t′+u+u′ is an integer from 8 to 38; and z is an integer of greater than or equal to 1.

22. A polycarbonate polymer comprising:

a) an isosorbide unit derived from an isosorbide of formula (2a):

b) an aliphatic unit derived from C 14-44 aliphatic diacid of formula (11):

where m and m′ are independently 0 to 38, n and n′ are independently 0 to 38, and the sum m+m′+n+n′ is an integer from 8 to 38, or

a C 14-44 aliphatic diol of formula (12):

where t and t′ are independently 0 to 38, u and u′ are independently 0 to 38, and the sum t+t′+u+u′ is an integer from 8 to 38, or

a combination of the C 14-44 aliphatic diacid of formula (11) and the C 14-44 aliphatic diol of formula (12); and

c) optionally, an additional unit different from the isosorbide and aliphatic units,

wherein the isosorbide unit, aliphatic unit, and additional unit are carbonate, or a combination of carbonate and ester units,

wherein the molecular weight of the polycarbonate polymer is greater than about 39,000 g/mol as measured by gel permeation chromatography relative to polystyrene standards,

wherein the glass transition temperature of the polycarbonate polymer is less than or equal to 135° C., and

wherein the weight % of aliphatic unit is between 14 and 22 wt % based on the total weight of the polycarbonate polymer.

23. A thermoplastic composition, comprising the polycarbonate polymer of claim 1 , and an additional polymer, an additive, or a combination of additional polymer and additive.

24. The thermoplastic composition of claim 23 , wherein the additional polymer comprises a polycarbonate, polysiloxane-polycarbonate, polyester-polycarbonate, polyester, impact modifier, or a combination comprising at least one of the foregoing polymers, and wherein the additive comprises an acid additive, an epoxy additive, a filler, an ionizing radiation stabilizer, an antioxidant, a heat stabilizer, a light stabilizer, an ultraviolet light absorber, a plasticizer, a lubricant, a mold release agent, an antistatic agent, a pigment, a dye, a flame retardant, an anti-drip agent, or a combination comprising at least one of the foregoing additives.

25. The thermoplastic composition of claim 24 , wherein the impact modifier comprises a methacrylate-butadiene-styrene (MBS) terpolymer.