Method of making isosorbide polycarbonate
View Patent ↗A polycarbonate is provided that contains repeat units derived from isosorbide and a residue derived from an activated diaryl carbonate. The polycarbonate has 1 H-NMR peaks associated with the repeat units derived from isosorbide. The polycarbonate contains no more than a maximum allowable amount of sorbitol-derived color bodies. If these color bodies are present in the polycarbonate it has a 1 H-NMR peak associated with the color bodies. The maximum allowable amount of color bodies are present when the integrated area of the 1 H-NMR peak associated with the color bodies divided by the integrated areas of the 1 H-NMR peaks associated with the repeat units derived from isosorbide is 0.025.
1. A method of producing an isosorbide-containing polycarbonate comprising the steps of:
(i) providing a first monomer component comprising isosorbide,
(ii) performing a monomer component conditioning step selected from the group consisting of: (a) testing the first monomer component for the presence of sorbitol, and if sorbitol is present, treating the first monomer component to reduce the level of sorbitol to an amount less than 0.10 mole % in the first monomer component, and (b) treating the first monomer component to reduce the level of sorbitol to an amount less than 0.10 mole % in the first monomer component,
(iii) forming a reaction mixture by adding a diaryl carbonate and a catalyst to the first monomer component, and
(iv) allowing the reaction mixture to react under polymerization conditions to build molecular weight, thereby producing an isosorbide-containing polycarbonate.
2. The method of claim 1 , wherein the method further comprises the step of adding one or more additional monomer components to the first monomer component selected from the group consisting of: BPA, C 36 branched fatty diol, C 36 diacid, dodecanedioic acid, and sebacic acid.
3. The method of claim 2 , wherein the one or more additional monomer components comprise BPA and C 36 diacid.
4. The method of claim 1 , wherein the method is accomplished by performing step (iii) before or after (ii).
5. The method of claim 1 , wherein the monomer component conditioning step (ii) is performed to reduce the level of sorbitol to an amount less than 0.05 mole % in the first monomer component.
6. The method of claim 5 , wherein the monomer component conditioning step (ii) is performed to reduce the level of sorbitol to an amount less than 0.01 mole % in the first monomer component.
7. The method of claim 1 , wherein in step (iv) the reaction mixture reacts under melt polymerization conditions to prepare polycarbonate, the catalyst is a melt transesterification catalyst, and the diaryl carbonate comprises an ester-substituted diaryl carbonate.
8. The method of claim 1 , further comprising the step of:
(v) performing a polycarbonate treatment step selected from the group consisting of: (a) testing the polycarbonate for the presence of a sorbitol-derived color body associated with a NMR peak located over a chemical shift at about 2.55 ppm in a 1 H-NMR spectrum, and if the sorbitol-derived color body is present, treating the polycarbonate prepared in step (i) to reduce the level of the sorbitol-derived color body, and (b) treating the polycarbonate to reduce the level of the sorbitol-derived color body.
9. A method of producing an isosorbide-containing polycarbonate, comprising the steps of:
(i) preparing a polycarbonate by reacting isosorbide with a diaryl carbonate in the presence of a polymerization catalyst under polymerization conditions, and
(ii) performing a polycarbonate treatment step selected from the group consisting of: (a) testing the polycarbonate prepared in step (i) for the presence of a sorbitol-derived color body associated with a 1 H-NMR peak located at a chemical shift of about 2.55 ppm in a 1 H-NMR spectrum, and if the sorbitol-derived color body is present, treating the polycarbonate prepared in step (i) to reduce the level of the sorbitol-derived color body, and (b) treating the polycarbonate prepared in step (i) to reduce the level of the sorbitol-derived color body, thereby producing an isosorbide-containing polycarbonate product.
10. The method of claim 9 , wherein in step (ii) the polycarbonate prepared in step (i) is tested for the presence of the sorbitol-derived color body using 1 H-NMR analysis, UV vis spectra analysis, X-Rite analysis, or by visually comparing the polycarbonate produced in step (i) with known color standards for polycarbonate.
11. The method of claim 9 , wherein in step (ii) the polycarbonate prepared in step (i) is treated to reduce the presence of the sorbitol-derived color body by dissolving the polycarbonate in a solvent and precipitating the polycarbonate from solution.
12. The method of claim 11 , wherein the solvent is a chlorinated solvent selected from the group consisting of chloroform and dichloromethane.
13. The method of claim 9 , wherein step (ii) is performed to reduce the concentration of the sorbitol-derived color body in the polycarbonate produced in step (i) such the polycarbonate product has less than 50% of the area contained under the 1 H-NMR peak located at a chemical shift of about 2.55 ppm in a 1 H-NMR spectrum of the product polycarbonate than does the polycarbonate produced in step (i).
14. The method of claim 9 , wherein step (ii) is performed to reduce the concentration of the sorbitol-derived color body in the polycarbonate produced in step (i) such the polycarbonate product has less than 25% of the area contained under the 1 H-NMR peak spanning a chemical shift of about 2.55 ppm in a 1 H-NMR spectrum of the product polycarbonate than does the polycarbonate produced in step (i).
15. The method of claim 9 , wherein step (ii) is performed to decrease the YI of the polycarbonate as measured using UV Vis spectrometry by a value of 2 or more.
16. The method of claim 9 , wherein step (i) is performed by reacting the isosorbide with a diaryl carbonate in the presence of one or more additional monomer components selected from the group consisting of: BPA, C 36 branched fatty diol, C 36 diacid, dodecanedioic acid, and sebacic acid.
17. The method of claim 16 , wherein the one or more additional monomer components comprise BPA and C 36 diacid.
18. The method of claim 10 , wherein in step (i) the reaction mixture reacts under melt polymerization conditions to prepare polycarbonate, wherein the catalyst is a melt polymerization catalyst and the diaryl carbonate comprises and activated diaryl carbonate.
19. A polycarbonate comprising repeat units derived from isosorbide, and a residue derived from an activated diaryl carbonate,
wherein the polycarbonate has 1 H-NMR peaks associated with the repeat units derived from isosorbide and wherein the polycarbonate contains no more than a maximum allowable amount of sorbitol-derived color bodies, wherein if sorbitol-derived color bodies are present in the polycarbonate, the polycarbonate has a 1 H-NMR peak associated with the sorbitol-derived color bodies, and
wherein the maximum allowable amount of sorbitol-derived color bodies are present when the integrated area of the 1 H-NMR peak associated with the sorbitol-derived color bodies divided by the total combined integrated areas of the 1 H-NMR peaks associated with the repeat units derived from isosorbide is 0.025.
20. The method of claim 19 , wherein the polycarbonate contains sorbitol-derived color bodies and wherein the integrated area of the 1 H-NMR peak associated with the sorbitol-derived color bodies divided by the total combined integrated areas of the 1 H-NMR peaks associated with the repeat units derived from isosorbide is less than 0.01.
21. The polycarbonate of claim 19 , wherein the polycarbonate contains no detectable amount of sorbitol-derived color bodies.
22. The polycarbonate of claim 19 , wherein the residue derived from an activated diaryl carbonate is derived from an ester-substituted diaryl carbonate and the residue comprises methyl salicylate.