Process for preparing polyestercarbonates
View Patent ↗Processes for preparing polyestercarbonates are disclosed. The processes allow for the consistent incorporation of adipic acid into a polymer generated from a dihydroxy compound, such as bisphenol-A, at levels greater than 99%. The polyestercarbonates so produced, as well as articles formed from the polyestercarbonates, are also disclosed herein.
1. A process for producing a polyestercarbonate, comprising:
preparing an initial mixture comprising water, a substantially water-immiscible organic solvent, a dihydroxy compound, a catalyst, and adipic acid, wherein the volume ratio of organic solvent to water is 10:1 or more;
reacting the initial mixture by adding phosgene at a first phosgenation rate until the molar ratio of phosgene added to the sum of the dihydroxy compound and the adipic acid is at least 70 percent, while maintaining the pH between about 4 and about 6 to form a reaction mixture;
raising the pH to about 9.5; and
maintaining the pH at about 9.5 for a period of time of from about 5 minutes to about 60 minutes.
2. The process of claim 1 , wherein the organic solvent is methylene chloride.
3. The process of claim 1 , wherein the catalyst is triethylamine.
4. The process of claim 1 , wherein the volume ratio of organic solvent to water of the initial mixture is about 20:1 or more.
5. The process of claim 1 , wherein the molar ratio of catalyst to the sum of the dihydroxy compound and the adipic acid in the initial mixture is at least 4 percent.
6. The process of claim 1 , wherein the molar ratio of catalyst to the sum of the dihydroxy compound and the adipic acid in the initial mixture is about 5 percent or more.
7. The process of claim 1 , wherein the molar ratio of catalyst to the sum of the dihydroxy compound and the adipic acid in the initial mixture is about 8 percent or more.
8. The process of claim 1 , further comprising adding phosgene to the reaction mixture at a second phosgenation rate while the pH of the reaction mixture is maintained at about 9.5.
9. The process of claim 1 , 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 aliphatic, 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 aliphatic, C 1 -C 12 alkyl, C 6 -C 20 aromatic, and C 6 -C 20 cycloaliphatic.
10. The process of claim 1 , wherein the first phosgenation rate is such that the molar ratio of phosgene added to the sum of the dihydroxy compound and the adipic acid does not reach 70 percent until after 20 minutes.
11. The process of claim 1 , wherein the initial mixture further comprises an endcapping agent.
12. The process of claim 1 , wherein an endcapping agent is added to the initial mixture along with the carbonate precursor.
13. The polyestercarbonate formed by the process of claim 1 .
14. An article formed from the polyestercarbonate of claim 13 .
15. A process for preparing a polyestercarbonate, comprising:
preparing an initial mixture comprising water, a substantially water-immiscible organic solvent, a dihydroxy compound, a catalyst, and adipic acid, wherein the molar ratio of catalyst to the sum of the dihydroxy compound and the adipic acid is at least 4 percent;
reacting the initial mixture by adding phosgene at a first phosgenation rate until the molar ratio of phosgene added to the sum of the dihydroxy compound and the adipic acid is at least 70 percent, while maintaining the pH between about 4.5 and about 6.0 to form a reaction mixture; and
adding phosgene while maintaining the pH at about 9.5 for a period of time of from about 20 minutes to about 40 minutes.
16. The process of claim 15 , wherein the volume ratio of organic solvent to water of the initial mixture is 10:1 or more.
17. The polyestercarbonate formed by the process of claim 15 .
18. An article formed from the polyestercarbonate of claim 17 .
19. A process for producing a polyestercarbonate, comprising:
preparing an initial mixture comprising water, a substantially water-immiscible organic solvent, a dihydroxy compound, a catalyst, and adipic acid, wherein (i) the volume ratio of organic solvent to water is 10:1 or more and (ii) the molar ratio of catalyst to the sum of the dihydroxy compound and the adipic acid is at least 4 percent;
reacting the initial mixture by adding phosgene at a first phosgenation rate until the molar ratio of phosgene added to the sum of the dihydroxy compound and the adipic acid is at least 70 percent, while maintaining the pH between about 4 and about 6 to form a reaction mixture;
raising the pH to about 9.5; and
adding phosgene while maintaining the pH at about 9.5 until the reaction is substantially complete.
20. The process of claim 19 , wherein the volume ratio of organic solvent to water of the initial mixture is about 20:1 or more.
21. The process of claim 19 , wherein the molar ratio of catalyst to the sum of the dihydroxy compound and the adipic acid in the initial mixture is about 5 percent or more.
22. The process of claim 19 , wherein the molar ratio of catalyst to the sum of the dihydroxy compound and the adipic acid in the initial mixture is about 8 percent or more.
23. The polyestercarbonate formed by the process of claim 19 .
24. An article formed from the polyestercarbonate of claim 23 .