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

a polysiloxane block,

wherein the isosorbide unit, aliphatic unit, and polysiloxane block 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 , further comprising an additional unit derived from a dihydroxy aromatic compound.

5. The polycarbonate polymer of claim 4 , 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 1-12 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).

6. The polycarbonate polymer of claim 5 , 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.

7. 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.

8. 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.

9. The polycarbonate polymer of claim 8 , wherein the amount of structural endgroup is less than 2,000 ppm based on the weight of the polycarbonate polymer.

10. The polycarbonate polymer of claim 1 , wherein the polysiloxane block is derived from a siloxane-containing dihydroxy compound that contains diorganosiloxane units of formula (15):

wherein each occurrence of R is same or different, and is a C 1-13 monovalent organic group and E has an average value of about 2 to about 1,000.

11. The polycarbonate polymer of claim 1 , wherein the polysiloxane block is derived from a siloxane-containing dihydroxy compound that contains diorganosiloxane units of formula (16):

wherein E has an average value of about 2 to about 1,000; each R is the same or different, and is a C 1-13 monovalent organic group; and each Ar is the same or different, and is a substituted or unsubstituted C 6 -C 30 arylene group, wherein the bonds are directly connected to an aromatic moiety.

12. The polycarbonate polymer of claim 11 , wherein the Ar groups are derived from a dihydroxyaromatic compound selected from the group consisting of 1,1-bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 1,1-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)n-butane, 2,2-bis(4-hydroxy-1-methylphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclohexane, bis(4-hydroxyphenyl sulfide), 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, and 1,1-bis(4-hydroxy-t-butylphenyl)propane.

13. The polycarbonate polymer of claim 1 , wherein the polysiloxane block is derived from a siloxane-containing dihydroxy compound that contains diorganosiloxane units of formula (17):

wherein E has an average value of about 2 to about 1,000; each R is the same or different, and is a C 1-13 monovalent organic group, and each R 6 is independently a divalent C 1 -C 30 organic group.

14. The polycarbonate polymer of claim 1 , wherein the polysiloxane block is derived from a siloxane-containing dihydroxy compound that contains diorganosiloxane units of formula (18):

wherein E has an average value of about 2 to about 1,000; each R is the same or different, and is a C 1-13 monovalent organic group, R 7 is a divalent C 2 -C 8 aliphatic group, each M can be the same or different, and is a halogen, cyano, nitro, C 1 -C 8 alkylthio, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy group, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 6 -C 10 aryl, C 6 -C 10 aryloxy, C 7 -C 12 aralkyl, C 7 -C 12 aralkoxy, C 7 -C 12 alkylaryl, or C 7 -C 12 alkylaryloxy, wherein each n is independently 0, 1, 2, 3, or 4.

15. The polycarbonate polymer of claim 14 , wherein M is bromo, chloro, an alkyl group, an alkoxy group, or an aryl group; R 7 is a dimethylene, trimethylene or tetramethylene group; and R is a C 1-8 alkyl, C 1-8 haloalkyl, or aryl.

16. The polycarbonate polymer of claim 14 , wherein R is methyl, or a combination of methyl and trifluoropropyl, or a combination of methyl and phenyl.

17. The polycarbonate polymer of claim 14 , wherein M is methoxy, n is one, R 7 is a divalent C 1 -C 3 aliphatic group, and R is methyl.

18. 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) a polysiloxane block

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

19. A polycarbonate polymer comprising:

an isosorbide unit derived from an isosorbide of formula (2b), formula (2c), formula (2d) or a combination comprising at least one of the foregoing

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

a polysiloxane block comprising units derived from a siloxane-containing dihydroxy compound that contains diorganosiloxane units of formula (15):

wherein each occurrence of R is same or different, and is a C 1-13 monovalent organic group and E has an average value of about 10 to about 70,

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