Copolycarbonate-polyesters, methods of manufacture, and uses thereof
View Patent ↗A copolycarbonate-polyester, comprising units of formula wherein at least 60 percent of the total number of R 1 groups are divalent aromatic organic radicals and the balance thereof are divalent aliphatic or alicyclic radicals; units of formula wherein T is a C 7-20 divalent alkyl aromatic radical or a C 6-20 divalent aromatic radical, and D is a divalent C 6-20 aromatic radical; and units of the formula wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a methyl or phenyl group, each c is independently 0 to 4, and T is as described above. A method of making a copolycarbonate-polyester is also disclosed.
1. A method of preparing a copolycarbonate-polyester, comprising
reacting a reactive polyester intermediate comprising
units of formula
wherein T is a C 7-20 divalent alkyl aromatic radical or a C 6-20 divalent aromatic radical, and D is a divalent C 6-20 aromatic radical; and units of formula
wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a methyl or phenyl group, each c is independently 0 to 4,
with a carbonate source in a reaction mixture comprising water, a substantially water-immiscible organic solvent, and a base, to provide a copolycarbonate-polyester.
2. The method of claim 1 , wherein at least a portion of the D groups are derived from a dihydroxy compound of the formula
wherein R a and R b are each independently a halogen atom or a monovalent C 1 -6 alkyl group; p and q are each independently integers of 0 to 4; and X a is one of the following groups:
wherein R c and R d are each independently a hydrogen atom or a C 1-29 alkyl group, or R c , C, and R d taken together are a divalent C 3-10 cycloalkyl group that is optionally substituted with one or more C 1-10 alkyl groups, and R e is a divalent hydrocarbon group.
3. The method of claim 2 , wherein at least a portion of the D groups are derived from bisphenol A.
4. The method of claim 1 , wherein each c is 0.
5. The copolycarbonate-polyester prepared by the method of claim 1 .
6. The copolycarbonate-polyester of claim 5 , wherein the copolycarbonate-polyester comprises units of the formula
wherein at least 60 percent of the total number of R 1 groups are divalent aromatic organic radicals and the balance thereof are divalent aliphatic, alicyclic or aromatic radicals; units of the formula
wherein T is a C 7-20 divalent alkyl aromatic radical or a C 6-20 divalent aromatic radical, and D is a divalent C 6-20 aromatic radical; and units of formula
wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, each c is independently 0, and
wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 50% of the total number of R 1 groups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
7. The copolycarbonate-polyester of claim 6 , wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 40% of the total number of R 1 groups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
8. The copolycarbonate-polyester of claim 6 , wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 30% of the total number of Rgroups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
9. The copolycarbonate-polyester of claim 6 , wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 20% of the total number of R 1 groups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
10. The copolycarbonate-polyester of claim 6 , wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 10% of the total number of R 1 groups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
11. The copolycarbonate-polyester of claim 6 , wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 1% of the total number of R 1 groups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
12. The copolycarbonate-polyester of claim 6 , having a Tg of 180° C. to 300° C.
13. The copolycarbonate-polyester of claim 6 , wherein T is a divalent isophthaloyl radical and/or a divalent terephthaloyl radical.
14. An article comprising the copolycarbonate-polyester manufactured by the method of claim 1 .
15. An article comprising the copolycarbonate-polyester of claim 6 .
16. A method of preparing a copolycarbonate-polyester, comprising
reacting a reactive polyester intermediate comprising
units of formula
wherein T is a C 7-20 divalent alkyl aromatic radical or a C 6-20 divalent aromatic radical, and R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, each c is independently 0,
with a carbonate source and a compound of the formula HO—R 1 —OH in a reaction mixture comprising water, a substantially water-immiscible organic solvent, and a base, to provide a copolycarbonate-polyester,
wherein R 1 is a divalent aromatic organic radical.
17. The method of claim 16 , wherein HO—R 1 —OH is bisphenol A.
18. The copolycarbonate-polyester prepared by the method of claim 16 .
19. The copolycarbonate-polyester of claim 18 , wherein the copolycarbonate-polyester comprises units of the formula
wherein at least 60 percent of the total number of R 1 groups are divalent aromatic organic radicals and the balance thereof are divalent aliphatic, alicyclic or aromatic radicals; units of the formula
wherein T is a C 7-20 divalent alkyl aromatic radical or a C 6-20 divalent aromatic radical, and D is a divalent C 6-20 aromatic radical; and units of formula
wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, each c is independently 0, and
wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 50% of the total number of R 1 groups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
20. The copolycarbonate-polyester of claim 19 , wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 10% of the total number of R 1 groups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
21. The copolycarbonate-polyester of claim 19 , wherein the number of R 1 groups that are derived from a monomer of the formula
is less than 1% of the total number of R 1 groups, and wherein R 2 and R 3 are each independently a halogen or a C 1-6 alkyl group, R 4 is a phenyl group, and each c is independently 0.
22. The copolycarbonate-polyester of claim 19 , having a Tg of 180° C. to 300° C.
23. The copolycarbonate-polyester of claim 19 , wherein T is a divalent isophthaloyl radical and/or a divalent terephthaloyl radical.
24. An article comprising the copolycarbonate-polyester manufactured by the method of claim 16 .