Polymers made from bis(2-hydroxyethyl)isosorbide and enduses thereof

Abstract

This invention provides a new, biomass-derived glycol, bis(2-hydroxyethyl)isosorbide, which is found to be a valuable monomer for a wide variety of polymeric materials

Description

[0001] This invention provides a new, biomass-derived glycol, bis(2-hydroxyethyl)isosorbide, which is found to be a valuable monomer for a wide variety of polymeric materials.TECHNICAL BACKGROUND OF THE INVENTION[0002] There is a desire to utilize polymeric components ultimately derived from biomass. The diol 1,4:3,6-dianhydro-D-sorbitol, hereinafter referred to as isosorbide, is readily made from renewable resources, such as sugars and starches. For example, isosorbide can be made from D-glucose by hydrogenation followed by acid-catalyzed dehydration. The preparation of isosorbide is known within the literature in, for example, G. Fleche, et. al., Starch / Starke, 38(1), pp. 26-30 (1986). Isosorbide has the additional advantage of increasing the heat resistance of a polyester into which it is incorporated by raising-its glass transition temperature (Tg).[0003] Charbonneau, et. al., in U.S. Pat. No. 6,063,464, describe a process to produce polyesters which incorporate isosorbide, that...

AI Technical Summary

Benefits of technology

[0012] The bis(2-hydroxyethyl)isosorbide of the present invention may be readily prepared from isosorbide, which is derived from renewable resources, such as sugars and starches, as described above. For example, isosorbide may be modified with ethylene oxide, ethylene carbonate and the like, to produce bis(2-hydroxyethyl)isosorbide.

Problems solved by technology

As one skilled in the art would appreciate, this inefficiency of isosorbide monomer incorporation into the polymer leads to complex glycol recovery and separation processes.

Significant cyclic oligomer levels in polymeric materials are not desirable for most end uses described herein.

The inadequate treatment of municipal solid waste which is being put in landfills and the increasing addition of nondegradable materials, including plastics, to municipal solid waste streams are combining to drastically reduce the number of landfills available and to increase the costs of municipal solid waste disposal.

While recycling of reusable components of the waste stream is desirable in many instances, the costs of recycling and the infrastructure required to recycle materials is sometimes prohibitive.

In addition, there are some products which do not easily fit into the framework of recycling.

One of the limitations to marketing such compost is the visible contamination by undegraded plastic, such as film or fiber fragments.

However, these PET sheets have poor low temperature impact strength, a low glass transition temperature (Tg) and a high rate of crystallization.

Thus, PET sheets cannot be used at low temperatures because of the danger of breakage and they cannot be used at high temperatures because the polymer crystallizes, thereby diminishing optical clarity.

However, polycarbonate has poor solvent resistance, thereby limiting its use in certain applications, and is prone to stress induced cracking.

Polycarbonate sheets also provide greater impact strength than is needed for certain applications, making them costly and inefficient for use.

At the same time, the comonomer may have the undesirable effect of lowering the glass transition temperature and reducing the crystallinity of PET.