Macro-cyclic polyester oligomers produced directly from diols and aromatic dicarboxylic acids, and related methods
AssigneeJM Mihalich LLC
InventorJames Mihalich
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Abstract
Known methods of production of macro-cyclic oligomers involve either (i) the depolymerization of a previously prepared polymer using a high dilution process to establish a thermodynamic equilibrium that favors cyclics over polymers, or (ii) using acid chlorides and diols in one or two solvent systems. As presented herein, it is found that by using a selected composition, a moisture tolerant catalyst, a suitable solvent, and a limited concentration profile, macro-cyclic oligomers can be produced directly in a one-step process, eliminating the need to first produce polymer or perform other additional process steps.
Claims12
A method for manufacturing a macro-cyclic polyester oligomer, the method comprising reacting an aromatic dicarboxylic acid with a diol in the presence of a catalyst to form the macrocyclic polyester oligomer, wherein the catalyst is a moisture tolerant catalyst.
A method for manufacturing a polyester (e.g., a polyarylate), the method comprising reacting an aromatic dicarboxylic acid with a diol in the presence of a catalyst to form the polyester, wherein the catalyst is a moisture tolerant catalyst.
The method of any one of the preceding claims, wherein the catalyst is a heterogeneous catalyst (e.g., a solid, or deposited on a solid) and the method comprises passing a solution comprising the aromatic dicarboxylic acid and the diol over a catalyst bed (e.g., wherein the method is a continuous process).
The method of any one of the preceding claims, wherein the method comprises reacting the aromatic dicarboxylic acid with the diol in a solvent solution, said solvent selected from the group consisting of dichloromethane, tetrahydrofuran, toluene, xylene, and chlorobenzene.
The method of any one of the preceding claims, wherein the method comprises reacting the aromatic dicarboxylic acid with the diol in a solvent solution, said aromatic dicarboxylic acid at a concentration from 0.02 to 0.3 molar in the solution, and said diol at a concentration from 0.02 to 0.3 molar in the solution.
The method of any one of the preceding claims, wherein at least 60 wt. % of the aromatic dicarboxylic acid is isophthalic acid (IPA) (e.g., with the remainder, e.g., 40 wt. % or less, terephthalic acid (TPA)).
The method of any one of the preceding claims, wherein the aromatic dicarboxylic acid is (i) isophthalic acid (IPA) or (ii) terephthalic acid (TPA) or (iii) a combination of IPA and TPA.
The method of any one of the preceding claims, further comprising producing a composite containing at least 60 wt. % reinforcing material using the macro-cyclic polyester oligomer or the polyester.
Dependencies are inferred from the claim text.