Isosorbide—containing polycarbonates and their preparation

1. A method of making an isosorbide-containing polymer, comprising subjecting at least one isosorbide-bisphenol of formula I:

and a formula I-reacting compound to polymerization conditions, wherein R1 is an isosorbide unit, and R2-R9 are independently selected from the group consisting of a hydrogen, a halogen, a C1-C6 alkyl, a methoxy, an ethoxy, and an alkyl ester, and wherein the formula I-reacting compound reacts with the bisphenol of formula I to form a structural unit that is polymerized into an isosorbide-containing polymer.

2. The method of claim 1 , wherein the isosorbide-bisphenol has a pKa value of between 8 and 11.

3. The method of claim 1 , wherein the isosorbide unit is derived from an isosorbide selected from the group consisting of 2,6-dioxabicyclo[3.3.0]octan-4,8-diol; 1,4:3,6-dianhydro-D-glucitol; 2,3,3a,5,6a-hexahydrofuro[3,2-b]furan-3,6-diol, and isomers thereof.

4. The method of claim 1 , wherein the isosorbide-containing polymer is a homopolymer.

5. The method of claim 1 , wherein the isosorbide-containing polymer is a copolymer.

6. The method of claim 1 , wherein the formula-I reacting compound is selected from the group consisting of a phosgene, a triphosgene, diacyl halide, dihaloformate, dicyanate, diester, diepoxy, diarylcarbonate, dianhydride, dicarboxylic acid, and diacid chloride.

7. The method of claim 1 , wherein the structural unit is polymerized with a dihydroxy compound of formula II:

wherein Z is selected from a group consisting of an aromatic compound and an aliphatic compound.

8. The method of claim 7 , wherein the aromatic dihydroxy compound is selected from the group consisting of 4,4′(3,3,5-trimethylcyclohexylidene)diphenol; 4,4′-bis(3,5-dimethyl)diphenol, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 1,1-bis(4′hydroxy-3′methylphenyl)cyclohexane (DMBPC), 4,4′-1-methyl-4-(1-methyl-ethyl)-1,3-cyclohexandiyl]bisphenol (1,3 BHPM), 4-[1-[3-(4-hydroxyphenyl)-4-methylcyclohexyl]-1-methyl-ethyl]-phenol (2,8 BHPM), 3,8-dihydroxy-5a,10b-diphenyl-coumarano-2′,3′,2,3-coumarane (DCBP), 2-phenyl-3,3-bis(4-hydroxyphenyl)heptane, 2,4′-dihdroxydiphenylmethane, bis(2-hydroxyphenyl)metane, bis(4-hydroxyphenyl)methane, bis(4-hydroxy-5-nitrophenyl)methane, bis(4-hydroxy-2,6-dimethyl-3-methoxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxy-2-chlorophenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane (BPA), 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-ethylphenyl)propane, 2,2-bis(4-hydroxy-3-isopropylphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(3,5,3′,5′-tetrachloro-4,4′-dihydroxyphenyl)propane, bis(4-hydroxyphenyl)cyclohexymethane, 2,2-bis(4-hydroxyphenyl)-1-phenylpropane, 2,4-dihydroxyphenyl sulfone, 4,4′-dihydroxydiphenylsulfone (BPS), bis(4-hydroxyphenyl)methane (bisphenol F, BPF), 4,4′dihydroxy-1,1-biphenyl, 2,6-dihydroxy naphthalene, hydroquinone, resorcinol, C1-3 alkyl-substituted resorcinols, 3-(4-hydroxyphenyl)-1,1,3-trimethylindan-5-ol, 1-(4-hydroxyphenyl)-1,3,3-trimethylindan-5-ol, and 2,2,2′,2′-tetrahydro-3,3,3′,3′-tetramethyl-1,1′-spirobi[1H-indene]-6,6′-diol, 1,3-propylene glycol, 1,2-propylene glycol, 2,2-diethyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-ethyl-2-butyl-1,3-polypropanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 1,3-terbutanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2,2,4-tnmethyl-1,6-hexanediol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, and 2,2,4,4-tetramethyl-1,3-cyclobutanediol.

9. The method of claim 1 , wherein the polymerization conditions are selected from the group consisting of interfacial, melt, solid state, and solution.

10. A polymer formed from the method of claim 1 .

11. The polymer of claim 10 , wherein the polymer is selected from the group consisting of a polycarbonate, a polyurethane, a polyurea, a polyarylate, a polyester, a polyether, a polyetheramide, a polyformal, and a polyphenylene ether.

12. The polycarbonate of claim 11 , wherein the polycarbonate is

wherein n is greater than 1.

13. The polycarbonate of claim 11 , wherein the polycarbonate is

wherein z is an aromatic compound and n is greater than 1.

14. A method of making an isosorbide-containing polymer, comprising subjecting two or more monomers comprising an isosorbide unit to polymerization conditions, wherein each monomer has a pKa value of between 8 and 11.

15. The two or more monomers of claim 14 , wherein the isosorbide unit is derived from an isosorbide selected from the group consisting of 2,6-dioxabicyclo[3.3.0]octan-4,8-diol; 1,4:3,6-dianhydro-D-glucitol; 2,3,3a,5,6a-hexahydrofuro[3,2-b]furan-3,6-diol, and isomers thereof.

16. The method of claim 14 , wherein the two or more monomers form a homopolymer.

17. The method of claim 14 , wherein the two or more monomers form a copolymer.

18. The method of claim 14 , wherein the two or more monomers are interfacially polymerized with a dihydroxy compound of formula II:

wherein Z is selected from the group consisting of an aromatic compound and an aliphatic compound.

19. The method of claim 18 , wherein the aromatic dihydroxy compound is selected from the group consisting of 4,4′(3,3,5-trimethylcyclohexylidene)diphenol; 4,4′-bis(3,5-dimethyl)diphenol, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 1,1-bis(4′hydroxy-3′methylphenyl)cyclohexane (DMBPC), 4,4′-1-methyl-4-(1-methyl-ethyl)-1,3-cyclohexandiyl]bisphenol (1,3 BHPM), 4-[1-[3-(4-hydroxyphenyl)-4-methylcyclohexyl]-1-methyl-ethyl]-phenol (2,8 BHPM), 3,8-dihydroxy-5a,10b-diphenyl-coumarano-2′,3′,2,3-coumarane (DCBP), 2-phenyl-3,3-bis(4-hydroxyphenyl)heptane, 2,4′-dihdroxydiphenylmethane, bis(2-hydroxyphenyl)metane, bis(4-hydroxyphenyl)methane, bis(4-hydroxy-5-nitrophenyl)methane, bis(4-hydroxy-2,6-dimethyl-3-methoxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxy-2-chlorophenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane (BPA), 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-ethylphenyl)propane, 2,2-bis(4-hydroxy-3-isopropylphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(3,5,3′,5′-tetrachloro-4,4′-dihydroxyphenyl)propane, bis(4-hydroxyphenyl)cyclohexymethane, 2,2-bis(4-hydroxyphenyl)-1-phenylpropane, 2,4-dihydroxyphenyl sulfone, 4,4′-dihydroxydiphenylsulfone (BPS), bis(4-hydroxyphenyl)methane (bisphenol F, BPF), 4,4′dihydroxy-1,1-biphenyl, 2,6-dihydroxy naphthalene, hydroquinone, resorcinol, C1-3 alkyl-substituted resorcinols, 3-(4-hydroxyphenyl)-1,1,3-trimethylindan-5-ol, 1-(4-hydroxyphenyl)-1,3,3-trimethylindan-5-ol, 2,2,2′,2′-tetrahydro-3,3,3′,3′-tetramethyl-1,1′-spirobi[1H-indene]-6,6′-diol, 1,3-propylene glycol, 1,2-propylene glycol, 2,2-diethyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-ethyl-2-butyl-1,3-polypropanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 1,3-terbutanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2,2,4-tnmethyl-1,6-hexanediol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, and 2,2,4,4-tetramethyl-1,3-cyclobutanediol.

20. A polymer formed from the method of claim 14 .

21. The polymer of claim 20 , wherein the polymer is selected from the group consisting of a polycarbonate, a polyurethane, a polyurea, a polyarylate, a polyester, a polyether, a polyetheramide, a polyformal, and a polyphenylene ether.

22. The polycarbonate of claim 21 , wherein the polycarbonate is

wherein n is greater than 1.

23. The polycarbonate of claim 21 , wherein the polycarbonate is

wherein z is an aromatic compound and n is greater than 1.