Copolycarbonates, methods of manufacture, and uses thereof

1. A copolycarbonate of the formula

wherein

5 to 50 mole percent of the total number of R 1 groups is derived from a monomer of formula (2)

wherein each R f is independently at each occurrence a halogen atom, a hydrocarbon group having 1 to 10 carbons, or a halogen substituted hydrocarbon group having 1 to 10 carbons, and n is 0 to 4; and

50 to 95 mole percent of the R 1 groups are derived from a dihydroxy compound of formula (7)

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; or R 1 can be derived from arylene-containing compounds selected from 4,4′-dihydroxybiphenyl, 1,6-dihydroxynaphthalene, and 2,6-dihydroxynaphthalene, and the dihydroxy compound of formula (7) is not a compound of formula (2), and wherein

the copolycarbonate comprises at least 10% fewer carbonate linkages of formula (4)

than would be theoretically obtained in a random copolymer made from the same ratio of the monomer of formula (2) and the dihydroxy compound of formula (7) or the arylene-containing compounds.

2. The copolycarbonate of claim 1 , wherein n is zero.

3. The copolycarbonate of claim 1 , wherein the monomer of formula (2) is hydroquinone.

4. The copolycarbonate of claim 1 , wherein the dihydroxy compound is of the formula (7)

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.

5. The copolycarbonate of claim 4 , wherein each p and q are each zero and X a is 2,2-propylene.

6. The copolycarbonate of claim 5 , wherein n is zero.

7. The copolycarbonate of claim 5 , wherein the monomer of formula (2) is hydroquinone.

8. The copolycarbonate of claim 1 , wherein 10 to 40 mole % of the R 1 groups in the copolycarbonate are derived from a monomer of formula (2), and 60 to 90 mole % of the R 1 units are derived from another dihydroxy compound of formula (7) or the arylene-containing compounds.

9. The copolycarbonate of claim 1 , comprising 15 to 98% fewer carbonate linkages of formula (4) than would theoretically be obtained in a random copolymer made from the same ratio of the monomer of formula (2) and the dihydroxy compound of formula (7) or the arylene-containing compounds.

10. A method of preparing a copolycarbonate comprising 5 to 50 mole percent of units derived from a monomer of formula (2)

wherein each R f is independently at each occurrence a halogen atom, a hydrocarbon group having 1 to 10 carbons, or a halogen substituted hydrocarbon group having 1 to 10 carbons, and n is 0 to 4, the method comprising

forming a bischloroformate from a dihydroxy compound of formula (3)

HO—R 5 —OH  (3)

wherein at least 60% of the R 5 groups are aromatic, the dihydroxy compound of formula (3) is not a compound of formula (2), and the average number of units in the bischloroformate is 1 to 2, wherein the forming is performed by contacting the dihydroxy compound(s) in a substantially inert, substantially water-immiscible solvent with an aqueous alkali or alkaline earth metal solution and phosgene; and

reacting the monomer of formula (2) with the bischloroformate to produce a condensate, in a reaction system comprising water, a substantially inert, substantially water-insoluble organic liquid, base, and a phase transfer agent to form the copolycarbonate.

11. The method of claim 10 , further comprising contacting the condensate with an organic base to hydrolyze and condense residual bischloroformates in the condensate.

12. The method of claim 10 , wherein n is zero.

13. The method of claim 10 , wherein the monomer of formula (2) is hydroquinone.

14. The method of claim 10 wherein the reaction system has a pH of 7 to 10.

15. A copolycarbonate prepared by the method of claim 10 .

16. An article comprising the copolycarbonate of claim 1 .

17. An article comprising the copolycarbonate manufactured by the method of claim 10 .

18. A method of preparing a copolycarbonate comprising 5 to 50 mole percent of units derived from a monomer of formula (2)

wherein each R f is independently at each occurrence a halogen atom, a hydrocarbon group having 1 to 10 carbons, or a halogen substituted hydrocarbon group having 1 to 10 carbons, and n is 0 to 4, the method comprising

forming a bischloroformate from a dihydroxy compound of formula (7)

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; or R 1 can be derived from arylene-containing compounds selected from 4,4′-dihydroxybiphenyl, 1,6-dihydroxynaphthalene, and 2,6-dihydroxynaphthalene;

wherein the dihydroxy compound of formula (7) is not a compound of formula (2), and the average number of units in the bischloroformate is less than 19; and

reacting the monomer of formula (2) with the bischloroformate, in a reaction system comprising water, a substantially inert, substantially water-insoluble organic liquid, base, and a phase transfer agent to form the copolycarbonate.

19. The method of claim 18 , wherein the average number of units in the bischloroformate is 1 to 3.

20. The method of claim 18 , wherein the average number of units in the bischloroformate is 1 to 2.