tech details

Poly (Hydroxyl Urethane) Adhesives and Binders from CO2-Based Intermediates

Opportunity

Research is currently inactive on the patented technology "Poly (Hydroxyl Urethane) Compositions and Methods of Making and Using the Same." The technology is available for licensing from the U.S. Department of Energy's National Energy Technology Laboratory.


Overview

Polyurethane compounds are useful in many commercial applications, including high-performance adhesives, surface coatings, sealants, binders, hydrogels, and resins. A polyurethane compound is any polymer composed of a chain of organic units joined by carbamate (—NCOO—) links. Polyurethanes are conventionally formed by the reaction of a diisocyanate and polyfunctional compounds in the presence of a catalyst. A major disadvantage of this synthesis method is the use of monomers containing toxic isocyanate groups. Recent emphasis has been placed on producing polyurethanes without the use of isocyanate through the reaction of a diamine and a molecule having one or more cyclic carbonate functional groups. Compounds resulting from this synthetic route are referred to as poly (hydroxyl urethanes) (PHUs) due to the presence of primary and/or secondary hydroxyl functional groups.

The current technology provides a single-step method for the synthesis of crossed-linked PHUs from CO2-based intermediates. Crossed-linked compositions are obtained through the use of cyclic carbonate chemistry involving the reaction of a CO2-derived cyclic carbonate, a thiol, and a compound having two or more amine functional groups. The synthetic process is efficient, simple, flexible, and scalable allowing for the production of less toxic, non-isocyanate containing PHU composites having adhesive properties.


Significance

  • Method utilizes inexpensive CO2 as a starting material
  • Synthesis produces environmentally friendly PHU compositions
  • Single step process allows for cross-linked PHU synthesis without the use of solvents
  • Scalable, high yield manufacturing process
  • Composites can be cured either thermally or with light


Applications

  • High performance polyurethane-based adhesives, surface coatings, sealants, binders, hydrogels, and resins


Related Patents

U.S. Patent No. 8,912,303, titled "Poly (Hydroxyl Urethane) Compositions and Methods of Making and Using the Same" issued December 16, 2014.

Inventors: David Luebke, Hunaid Nulwala, and Chau Tang

U.S. Patent No. 9,243,174, titled "Poly (Hydroxyl Urethane) Composites and Method of Making and Using the Same" issued January 26, 2016.

Inventors: David Luebke, Hunaid Nulwala, and Chau Tang

Additional information about this technology is available in the article "Tunable Poly (Hydroxyl Urethane) From CO2-Based Intermediates Using Thiol-ene Chemistry" in the Journal of Polymer Science Part A: Polymer Chemistry 2011, 49(9):2024-2032.