Sulfonated telechelic polycarbonates

1. A method for the melt synthesis of a telechelic sulfonated polycarbonate, comprising:

first reacting a mixture comprising a dihydroxy compound and a sulfobenzoic acid salt and a catalyst to obtain an intermediate product at a temperature of from about 190° C. to about 230° C.;

adding an activated carbonate to the mixture; and

then reacting the intermediate product with the activated carbonate to obtain the telechelic sulfonated polycarbonate;

wherein the dihydroxy compound has the structure of Formula (I):

wherein R 1 through R 8 are each independently selected from hydrogen, halogen, nitro, cyano, C 1 - C 20 alkyl, C 4 -C 20 cycloalkyl, and C 6 -C 20 aryl; and A is selected from a bond, —O—, —S—, —SO 2 —, C 1 -C 12 alkyl, C 6 -C 20 aromatic, and C 6 -C 20 cycloaliphatic;

the sulfobenzoic acid salt has the structure of Formula (II):

wherein M is an alkali metal; and Ar″ is an aromatic ring; and

the activated carbonate has the structure of Formula (III):

wherein each Q or Q′ is independently selected from alkoxycarbonyl, halogen, nitro, amide, sulfone, sulfoxide, imine, and cyano; Ar and Ar′ are independently aromatic rings; n and n′ are independently whole numbers from zero up to the number of replaceable hydrogen groups on each aromatic ring Ar and Ar′, wherein (n+n′)≧1; p is an integer from zero up to the number of replaceable hydrogen groups on aromatic ring Ar minus n; p′ is an integer from zero up to the number of replaceable hydrogen groups on aromatic ring Ar′ minus n′; and each R or R′ is independently selected from alkyl, substituted alkyl, cycloalkyl, alkoxy, aryl, alkylaryl having from 1 to 30 carbon atoms, cyano, nitro, halogen, and carboalkoxy.

2. The method of claim 1 , wherein the molar ratio of dihydroxy compound to sulfobenzoic acid salt is from about 99.9:0.1 to about 90:10.

3. The method of claim 1 , wherein the dihydroxy compound and sulfobenzoic acid salt are reacted for a period of from about 60 minutes to about 120 minutes.

4. The method of claim 1 , wherein the dihydroxy compound and sulfobenzoic acid salt are reacted at a pressure of from about 1.0 bar to about 1.5 bar.

5. The method of claim 1 , wherein the pressure is reduced to a range of from about 50 millibar to about 200 millibar after the activated carbonate is added.

6. The method of claim 1 , wherein the temperature is increased to a temperature of from about 250° C. to about 280° C. while the intermediate product and the activated carbonate are reacted.

7. The method of claim 1 , wherein the pressure is reduced to a pressure of from about 0.01 millibar to about 2 millibar while the intermediate product and the activated carbonate are reacted.

8. The method of claim 1 , wherein the intermediate product and the activated carbonate are reacted for a period of from about 30 minutes to about 120 minutes.

9. The method of claim 1 , wherein the catalyst is a system of tetramethyl ammonium hydroxide (TMAH) and sodium hydroxide (NaOH).

10. The method of claim 1 , wherein the telechelic sulfonated polycarbonate has a weight average molecular weight of greater than 30,000.

11. The method of claim 1 , wherein the dihydroxy compound is 2,2-bis(4-hydroxyphenyl) propane (bisphenol-A).

12. The method of claim 1 , wherein the sulfobenzoic acid salt is the phenyl ester of sulfobenzoic acid sodium salt.

13. The method of claim 1 , wherein the activated carbonate is bis(methylsalicyl)carbonate (BMSC).

14. A method for the synthesis of a telechelic sulfonated polycarbonate, comprising:

first reacting a mixture comprising bisphenol-A, a phenyl ester of a sulfobenzoic acid sodium salt, and a catalyst to obtain an intermediate product at a temperature of from about 190° C. to about 230° C.; and

then reacting the intermediate product with bis(methylsalicyl) carbonate (BMSC) to obtain the telechelic sulfonated polycarbonate.

15. The method of claim 14 , wherein the mixture is reacted for about 90 minutes at a temperature of about 210° C.

16. The method of claim 14 , further comprising reducing the pressure to 130 millibar during the reaction of the intermediate product with BMSC.

17. The method of claim 16 , wherein after the pressure is reduced to 130 millibar, the temperature is increased to about 260° C. and the pressure is further reduced to about 0.1 millibar.

18. A telechelic sulfonated polycarbonate, wherein at least 70 mole percent of the end groups of the polycarbonate are sulfonates of Formula (VI):

wherein M is an alkali metal and wherein the polycarbonate has a weight average molecular weight of greater than 30,000 as measured by as measured by GPC versus polystyrene standards.

19. The polycarbonate of claim 18 , wherein the polycarbonate is formed from the reaction of a dihydroxy compound and an activated carbonate.

20. The polycarbonate of claim 18 , wherein the polycarbonate is completely soluble in chloroform.

21. The polycarbonate of claim 18 , wherein the polycarbonate is transparent.

22. The telechelic sulfonated polycarbonate produced by the method of claim 1 .