Available Technologies from CSP Investigators

Beaker and flask with green liquid


Environmentally Friendly Thermoset from Sugar​

A process has been developed for synthesizing two new dimethacrylate monomers from glucose and mannose. The materials produced by the sugar-derived dilactones undergo degradation in basic conditions while remaining stable in neutral and acidic environments. The dimethacrylates are derived from sugars, making them renewable and comparable to petroleum-based sources. The monomers reported are sugar-derived dimethacrylates, and provide a pathway to create sustainable materials for use in coatings, thermosets, adhesives and particle-based drug delivery.

Inventor: Marc A. Hillmyer and Theresa M. Reineke


Isosorbide Based Block Polymers

An isosorbide-based methacrylate monomer has been synthesized and polymerized to produce block polymers. This new isosorbide derivative, acetylated methacrylic isosorbide (AMI), is easily synthesized from commercially available starting materials in just two steps. The AMI monomer can further be polymerized to form block copolymers.

Inventor: Marc A. Hillmyer and Theresa M. Reineke


Bio Based Polymer Synthesis from Sugar​

A method of creating a scalable block copolymer from a new branched lactone monomer has been developed. The new lactone monomer is generated from direct fermentation of sugar.  The biobased monomer, when copolymerized with lactide, has many utilities and its mechanical properties (i.e. stretchiness, strength) can be tuned depending on the application requirements. Sugar (glucose) is one of nature’s simplest and most common organic compounds, and the resultant polymers from this new process are biodegradable, affordable, and available for mass-production. Applications of these polymers are disposable materials, thermoplastics, and sustainable plastic components.

Inventor: Marc A. Hillmyer, Frank Bates, and Kechun Zhang


Heat Resistant Thermoplastic Made from Renewable, Biodegradable PLA

This heat resistant PLA is derived from the material lactide found in biomass such as corn starch, sugar, wheat, and sugar beets. This thermoplastic is an eco friendly alternative to Styrofoam or petroleum-based plastic due to the environmentally friendly creation process and the available renewable biomass sources.

Inventor: Marc A. Hillmyer


Biodegradable Polylactide Polymer from Polymerized Oil

Producing polylactide composites from polymerized oil increases the impact strength and tensile toughness over polylactides while remaining biodegradable. The composite is fabricated from polymerized natural oil such as soybean oil, castor oil, rapeseed oil, corn oil, coconut oil, etc. The composite is renewable and biodegradable, unlike many materials added to improve the properties of polylactide.

Inventor: Marc A. Hillmyer


Biodegradable Polyester Produced from Non-toxic, Renewable Monomer

A method has been developed to produce a biodegradable polyester known as poly(3-hydroxypropionic acid). The method combines the high-molecular weight and control aspects of ring-opening polymerization with the commercial availability of the beta hydroxy acid, 3-hydroxypropionic acid which is abbreviated as 3-HP. Since 3-HP can be derived from biological sources, the resulting material, poly(3-hydroxypropionic acid) or P(3-HP), is biorenewable. The new method allows direct synthesis of the bio-based polymer P(3-HP) from 3-HP, a commercial monomer that is derived from corn. The method uses a single vessel reactor for simple synthesis and rapid scale up. The method results in a higher molecular weight which makes the polymer more structurally sound using a process with lower toxicity than competing technologies.

Inventors: Marc A. Hillmyer and William B. Tolman


Nanostructured Membranes for Gas and Liquid Separation

The nanostructure separation membrane is size-tunable and can be fabricated using a low- cost method. The membrane has applications in water purification, fuel cells, gas separation, and ultrafiltration.

Inventor: Marc A. Hillmyer


Nanoporous Polymer Membrane Fabrication

A method has been created for the fabrication of nanoporous polymers with potential applications in ultrafiltration and other size selective separation functions. The polymer materials are especially useful for lithium ion battery applications, where they act as a separation layer, preventing the anode and cathode from coming into contact, while the small pore size of the highly porous polymer membrane does not affect the movement of the lithium ions. The material is chemically and mechanically robust with controllable pore sizes and high void fractions.

Inventor: Marc A. Hillmyer


Solid-State Polymer Electrolyte for Improved Lithium Batteries

A solid-state polymer electrolyte has been developed and can be used for safer, longer lasting, and lower cost lithium ion battery applications and enable higher energy density. The technology produces solid-state electrolytes that are less expensive, mechanically stronger and have better ionic conductivity than current electrolytes, enabling batteries that are smaller, safer and need replacing less often than current batteries.

Inventors: Marc A. Hillmyer and Timothy Lodge


Fluorination of Polymers Using Difluorocarbene Improves Oxidative and Chemical Stability

A method for the fluorination of polymers uses difluorocarbene to produce desired fluorinated polymers.  Difluorocarbene is a reactive species that can rapidly react with certain unsaturated parts of the polymer chain.  The reaction works under mild conditions and provides a low cost method of synthesizing fluorinated polymers.

Inventor: Marc A. Hillmyer


Olefin Synthesis from Biomass​

A catalytic process allows commodity olefins to be synthesized from the carboxylic acids of biomass. This bio-based feedstock approach is a desirable method for generating olefins that can be used to make plastics and other chemicals. The process, which involves the decarbonylation of carboxylic acids from biomass, creates olefins such as styrene, acrylates, acrylonitrile and octene in moderate to good yield. Furthermore, by adding a tandem Heck-type coupling reaction, the process can also generate stilbenes, which are desired bioactive targets.

Inventor: William B. Tolman and Marc A. Hillmyer


Polymer Nanoparticles Improve Delivery of Compounds

A method of creating polymer nanoparticles that contain hydrophobic additive compounds such as chemicals, cosmetics, drugs or pigments and improves the availability and delivery of the additive compound. This process results in a material that delivers higher concentrations of compound compared to other nanoparticle delivery materials.

Inventor: Christopher W. Macosko


Nanoparticle Chemotheraphy with Anticancer Prodrugs

A prodrug nanoparticle distribution technique has been developed that will aid in chemotherapy as a dispersal method of anticancer agents. Nanoparticles loaded with the prodrugs are protected from chemical reaction by the nanoparticles until they reach the reaction site, making them efficient options for drug targeting. This new treatment with nanoparticle-based prodrugs has higher permeation and retention of the anticancer agents into solid tumors than current chemotherapeutic treatments.

Inventors: Thomas Hoye, Christopher W. Macosko, and Jayanth Panyam


AMSOL 7.1: Software to Calculate Free Energies of Solvation

AMSOL is a computational chemistry software program that calculates the free energy of a solvated molecule. The software application calculates the change in energy when molecules are dissolved in water or an organic solvent.

Inventors: Christopher J. Cramer and Donald Truhlar


Small Aromatic Molecule Synthesis at Ambient Conditions Using Diels-Alder Reactions and Benzyne Intermeidates

A method has been developed to synthesize small molecules with complex aromatic core structures in high yields and at ambient conditions without a catalyst. By reducing the number of steps in the synthesis, the method has the potential to reduce the cost and increase efficiency in the synthesis of drugs, dyes and other aromatic compounds.

Inventor: Thomas R. Hoye


Biosynthetic Pathway to 1,4-Butanediol and other C4-C5 Chemicals

To reduce the costs of making valuable C4-C5 renewable chemicals, a biosynthetic pathway has been developed to generate C4-C5 chemicals, such as succinate, amino acids and 1,4-butanediol. This new pathway from sugars involves only five fermentation steps, as compared to the current pathway, which requires 23 steps. The new process uses engineered microbes and a simple pathway that produces less contaminating byproducts and higher yields (50% higher theoretical yield). This new approach makes the production of cost-effective renewable bioplastics, polyesters and spandex a possibility.

Inventor: Kechun Zhang


Biological Pathways Produce Isobutyric Acid Using Renewable Resources

Biological pathways that produce isobutyric acid from sugar-based feedstocks have been developed using fungal and bacterial enzymes. These biological pathways are more environmentally friendly and direct than chemical synthesis. Note: This technology for producing isobutyric acid has been exclusively licensed to Ascenix Biotechnologies.

Inventor: Kechun Zhang


Methyl Isobutyl Ketone from Glucose Using a Biobased Chemical Process

Methyl isobutyl ketone (MIBK) is an industrial solvent that is used in numerous applications, such as the manufacture of surface coatings, rubber chemicals, pharmaceuticals and adhesives. The current industrial production route for MIBK is problematic and costly, in that it involves a high pressure reaction, relies on petroleum as the feedstock, and operates at low yields of 10-30%. Note: This technology for producing methyl isobutyl ketone has been exclusively licensed to Ascenix Biotechnologies.

Inventor: Kechun Zhang


Catalytic Synthesis Of Fluorinated Anilines

UC Berkeley researchers have developed a reaction for the coupling of primary fluoroalkylamines with aryl bromides and aryl chlorides and occur in the presence of functional groups that are typically not tolerated by C-N coupling reactions. The reaction yield is high and can be conducted with low catalyst loadings for most substrates.

Inventors: John F. Hartwig


Additions and Rearrangements Catalyzed by Gold(I) Complexes

UC Berkeley Researchers have developed an air- and moisture-tolerant Au(I) catalyst for the acetylenic Claisen rearrangement. The gold catalyzed reaction provides access to a variety of homoallenic alcohols, which can be prepared enantio-enriched when employing a non-racemic propargyl vinyl ether. The reaction is highly stereo-selective and proceeds under mild conditions with low catalyst loading.

Inventor: F. Dean Toste


Optimized Catalyst to Improve Synthesis of Aliphatic Polyesters​

This invention describes an optimized catalyst that is used in the synthesis of new aliphatic polyesters with high molecular weight and low molecular weight distributions via alternating copolymerization of epoxides and cyclic anhydrides.

Inventors: Ryan Jeske, Geoffrey Coates, and Scott Allen


Stereocomplexation of Poly(propylene succinate) for the Synthesis of a Biorenewable Semicrystalline Polyesters

This invention describes a new aliphatic polyester stereocomplex formed from the mixture of racemic, isotactic, regioregular chains of poly(propylene succinate). The resulting material has a characteristic melting point approaching that of low density polyethylene.

Inventors: Geoffrey Coates and Julie Longo


Biodegradable Polylactic Acid Plastic is Strengthened with Co-Polymer

A process developed at the University of Minnesota can strengthen polylactic acid using less added material(as little as 1 wt% of non-polyactic acid material as opposed to 2-3 wt% for commercial additives) by creating a co-polymer. This added strength expands the potential polylatic acid applications to replacement of high impact polystyrene and packaging.

Inventors: Marc A. Hillmyer


Racemic Bimetallic Catalysts for the Isoselective Polymerization of Racemic Epoxides to Telechelic Isotactic Polyethers Polyols​

This invention relates to synthetically accessible bimetallic chromium complexes that along with chain shuttling agents, catalyze the polymerization of racemic epoxides to isotactic polyether polyols, particularly α,ω-Hydroxy telechelic poly(propylene oxide) (PPO).

Inventors: Geoffrey Coates and Matthew Childers


Direct and Efficient Synthesis of Poly(3-Hydroxybutyrate)

A direct and highly efficient, one-pot method for the synthesis of poly(3-hydroxybutyrate) (P3HB) from epoxides and CO. This process eliminates the need for purification of the toxic lactone intermediate.

Inventors: Geoffrey Coates and Erin Dunn


Method for Synthesizing Isotactic Polyethers

This technology introduces the only currently known method to synthesize end functionalized isotactic polyethers, including telechelic diols, from racemic epoxides by using a bimetallic catalyst and alcohol as chain transfer agent.

Inventors: Geoffrey Coates and Peter Widger


Nanoporous Filtration Membrane from Block Copolymer

A robust yet flexible nanoporous filtration membrane can be produced from block copolymer. The process begins by synthesizing a nanoporous cross-linked polystyrene-polyisoprene-polystyrene-polylactide tetrablock terpolymer that displays good tensile and elongation properties.

Inventors: Marc A. Hillmyer


Living Insertion/Cyclization/Ring-Opening Polymerization: A Strategy for the Synthesis of Functional Propylene Copolymers and Block Copolymers

A mechanism for the polymerization of 1,5-hexadiene with a perfluorinated bis(phenoxyimine) catalyst system is reported. The microstructure of the polymer contains the expected methylene-1,3-cyclopentane units as well as 3-vinyl tetramethylene units.

Inventors: Geoffrey Coates and Phillip Hustad


Polyisobutylene Alternative in Thermoplastic Polyurethanes

A monomer has been created that can be used to synthesize hydroxy-telechelic poly(ethylene-co-isobutylene) (PEIB) and is an alternative to polyisobutylene (PIB) in thermoplastic polyurethanes. PIB offers advantageous traits such as chemical resistance, low permeability and excellent stability, and is biocompatible and approved for use in biomedical applications. 

Inventors: Marc A. Hillmyer


Toughened Polylactic Acid

Brittle thermoplastics such as polylactide/polylactic acid (PLA) can be significantly toughened with amphiphilic block copolymers. 

Inventors: Frank Bates and Lorraine Francis


Organic Blue Light Emitting Compounds

New chemical structures capable of emitting saturated blue light can be easily synthesized. Potential applications include organic light emitting diodes (OLEDs), organic photovoltaic (OPV) devices, and/or organic field effect transistors (OFETs).

Inventors: Thomas Hoye 


Novel Solid Polymer Electrolyte Compositions for Improved Lithium-Metal Polymer Batteries

Solid polymer electrolyte (SPE) compositions containing a mechanically rigid phase and a novel cross-linker that displays both high conductivity and dendrite growth resistance at ambient temperature, for use in lithium-metal based batteries and related electrochemical energy storage devices.

Inventors: Geoffrey Coates and Rachna Khurana


Porous Cyclodextrin Polymer for Rapid Removal of Organic Contaminants in Water Purification

The invention provides alternative broad-spectrum sorbents for water purification and other applications, with superior adsorption kinetics.

Inventors: William Dichtel, Alaaeddin Alsbaiee, Brian Smith


Graphene-Catalyzed Growth of Covalent Organic Framework Thin Films for Solar Cells

Building on a previous invention to synthesize unique covalent organic frameworks (COF), this invention is a method to synthesize 2-dimensional COF thin films on single layer graphene-coated surfaces, which can solve the challenges of predictably assembling organic semiconductors into highly conductive structures.

Inventors: William Dichtel, Jiwoong Park, Mark Levendorf, John Colson, Eric Spitler, Arnab Mukherjee, and Arthur Woll


Synthesis of Graphene Nanoribbons

This invention is a novel method to convert conducting polymers into narrow strips of carbon semiconductors known as graphene nanoribbons (GNR), enabling graphene as a suitable substitute for silicon in high-performance nanoelectronic devices.

Inventors: William Dichtel and Hasan Arslan


Fluorescent Polymer Capable of Detecting Trace Explosives

A fluorescent polymer was invented that can sense trace amounts of RDX vapor to enable explosive devices and the individuals who prepare them to be identified. RDX is one of the most common components of plastic explosives and is frequently used in acts of terrorism.

 

Inventors: William Dichtel and Deepti Gopalakrishnan


Bio-Derived Methyl Butanediol and Methyl-Substituted Polyesters

A new process synthesizes multifunctional alcohols from bio-derived carboxylic acids. 

Inventors: Kechun Zhang and Paul Dauenhauer


High Performance Organic Cathodes for Thin Film Batteries

Cornell researchers created high performance pseudo-capacitive organic thin films for electrodes that create an energy storage system with the energy density of a battery and the power density of a supercapacitor.

Inventors: Geoffrey Coates, Hector Abruna, and Thanh-Tam Truong