Innovation to Commercialization: Case Studies · Paul Anastas Amy Cannon Julie Haack Jim Hutchison...

John C. Warner

President and Chief Technology OfficerWarner Babcock Institute for Green Chemistry, LLC

PresidentBeyond Benign

Innovation to Commercialization: Case Studies

[email protected]

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Green Chemistry is the design of chemical products and processes that reduce or eliminate the use and/or generation of hazardous substances.

1. Prevention. It is better to prevent waste than to treat or clean up waste after it is formed.

2. Atom Economy. Synthetic methods should be designed to maximize the incorporation of all materials used in the process into the final product.

3. Less Hazardous Chemical Synthesis. Whenever practicable, synthetic methodologies should be designed to use and generate substances that possess little or no toxicity to human health and the environment.

4. Designing Safer Chemicals. Chemical products should be designed to preserve efficacy of the function while reducing toxicity.

5. Safer Solvents and Auxiliaries. The use of auxiliary substances (solvents, separation agents, etc.) should be made unnecessary whenever possible and, when used, innocuous.

6. Design for Energy Efficiency. Energy requirements should be recognized for their environmental and economic impacts and should be minimized. Synthetic methods should be conducted at ambient temperature and pressure.

7. Use of Renewable Feedstocks. A raw material or feedstock should be renewable rather than depleting whenever technically and economically practical.

8. Reduce Derivatives. Unnecessary derivatization (blocking group, protection/deprotection, temporary modification of physical/chemical processes) should be avoided whenever possible .

9. Catalysis. Catalytic reagents (as selective as possible) are superior to stoichiometric reagents.

10. Design for Degradation. Chemical products should be designed so that at the end of their function they do not persist in the environment and instead break down into innocuous degradation products.

11. Real-time Analysis for Pollution Prevention. Analytical methodologies need to be further developed to allow for real-time in-process monitoring and control prior to the formation of hazardous substances.

12. Inherently Safer Chemistry for Accident Prevention. Substance and the form of a substance used in a chemical process should be chosen so as to minimize the potential for chemical accidents, including releases, explosions, and fires.

The Twelve Principles of Green Chemistry

Paul Anastas

Amy Cannon

Jim HutchisonJulie Haack

Julie Zimmerman

John Arnold

Marty Mulvihill Terry Collins

Robin Rogers

Mary Kirchoff

Joe Breen Robin Rogers

Martyn Poliakov

Martyn Poliakoff

Walter Leitner

Buxing Han

C.J. Li

Philip Jessup

James Clark

Colin Raston

Ken Seddon

Roger SheldonBarry Trost

Andrew Dicks

Irv Levy

Michael Korzenski

Stephen Ley

Bruce Lipshutz

Marty Mulvihill

Ed Brush

Jonathan Kenny

Dalila Kovacs

Bill Tolman

Wei Zang

Nick Anastas

G. Yadav

RK Sharma

Nitesh Mehta

Kei Saito

Kei Saito

Milton Hearn

John Warner

Deborah Martino

(SciFinder Data Collected September 30, 2015)

The past 25 years of green chemistry publications

0

5000

10000

15000

20000

25000

30000

35000

40000

1990 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015

Pu

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atio

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Cumulative Publications

Publications

Patents

Of all the products and processes…

Maybe 10% are benign…

Maybe 25% havealternatives available…

65% Still have to be invented!

More environmentally

benign than alternatives

Perform better

than alternatives

More economical

than alternatives

Green Chemistry

Safety

Performance Cost

Green

Chemistry

Green Chemistry

Chemists have ALWAYS cared about

Human Health and the Environment.

x HazardRisk = Exposure

The cost of using hazardous materials:

Storage

Transportation

Treatment

Disposal

Regulatory Costs

Liability

Worker Health and Safety

Corporate Reputation

Community Relations

New Employee Recruitment

Environmental Regulations

AMFAARPAA

AJAASBCAA

ESAA-AECAFFRAA

FEAPRAIRA

NWPAACODRA/NMSPAA

FCRPAMMPAA

120

110

100

90

80

70

60

50

40

30

20

10

01870 1880 1890 1900 1910 1920 1930 1940 1950 1960 1970 1980 1990 2000

EPACTFFCACERFACRAA

PPAPPVAIEREAANTPAGLCPAABACZARAWRDAEDPOPARECACAAAGCRAGLFWRAHMTUSANEEA

SDWAASARA

BLRAERDDAAEAWANOPPAPTSAUMTRCAESAAQGANCPA

TSCAFLPMARCRANFMACZMAA

NEPAEQIACAAEPAEEAOSHAFAWRAANPAA

FRRRPASOWADPA

WSRAEARCFHSA

AQA

NAWCA

WQA

NWPA

MPRSAAARPA

HMTA

FCMHSA

NHPA

WLDAFWCAA

FWAAEA

AEPA FIFRA PAA

FAWRAMBCANPSWA

IANBRA

AARHAYA

TAFWCA

BPA

NLRAWPA

AQAFOIA

WRPAAFCA

FHSANFMUA

BLBAFWPCAMPRSACZMA

NCAFEPCAPWSA

MMPA

ESATAPA

RCRAAWLDI

APASWDA

CERCLACZMIA

COWLDAFWLCA

MPRSAA

CAAACWA

SMCRASWRCASDWAA

Num

ber

of L

aws

Carbon-Carbon Bonds

Oxidations

Reductions

Hydroxylations

Polymer Syntheses

Traditional Processes Green Alternatives

100 Research DriveWilmington, MA 01887

John Warner Amy Cannon

James & Jim Babcock Joe Pont, CEO

2007 onward…

Fabrication & Physical Testing,

Analytical Separations

Lab

Microscopy & Surface Analysis

Lab

NMRLab

Particle Size & Surface Characterization Lab

Me

tal O

xid

e R

ese

arc

h L

abs

Organic & Polymer Synthesis

Lab

BiomaterialsLab

Thermal Analysis & Spectroscopy LabX

-ray

Lab

Environment & Toxicology

Lab

Multi-use Chemistry Lab

Beyond Benign

Ap

plic

ati

on

s an

d C

oat

ings

Res

ear

ch L

ab…

WBI Executive Office Space

WBI Scientists Office Space

Learning Center

Cafe

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s &

La

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up

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WBITechnology Greenhouse Technology Incubator

MarketAnalysis

Basic Research

Create

Create a potentially useful prototype.

Develop

Develop a potentially successful product.

Commercialize

Commercialize a successful product.

Science

Observe and define structure and dynamics.

Explore

Identify and characterize impact of changes of structure on dynamics and dynamics on structure.

Understand

Design alterations in structure and/or dynamics to purposefully control response.

Parameterize

Business

Explore Observe and define a product and market.

Understand Identify and characterize market

history and likely future trends

Parameterize Design potential products and assess potential

markets and parameters for success.

Contract Invention

Invent for collaborators

Help with commercialization

Self-Funded InventionPharmaceutical and

Agricultural Products

Cosmetics, Personal Care and Home Care

Materials and Composites

Sustainability Sciences

Performance Materials

Films and Coatings

Delta-S

Confidential - Warner Babcock Institute for Green Chemistry, LLC 21

Pharmaceuticals and Agricultural Products

Pharmaceutical and Agricultural Products





Films and Coatings

Cu ATSM

Parkinson’s/ALS Disease Therapeutic

“Non-Covalent Derivatives of Metal Complexes and Methods of Treatment”Warner, John C., Cheruku. Srinivasa R.; US Pat ApplicationNo. 61/932,348 January 28, 2014.“Copper (II) bis(N-alkyl-hydrazinecarbothioamide) Complexes as Non-Covalent Derivatives for the Treatment of CNS Conditions”Warner, John C., Cheruku. Srinivasa R.; US Pat ApplicationNo. 61/902,682 November 11, 2013.

0.001

0.01

0.1

1

10

100

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Aggregation EC50 (uM)

Disggregation EC50 (uM)

Apr 2012 Jun 2012 Sep 2012 Nov 2012 Jan 2013

log

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50

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CQ DisaggCQ Agg

PBT2 Disagg

PBT2 Agg

Alzheimer’s Disease Therapeutic

“Dihydro-6-Azaphenalene Derivatives for the Treatment of CNS, Oncological Diseases and Related Disorders” Warner, John C. et al., US PCT Application No.: PCT/US13/62429. September 27, 2013. Cthulhunol

“Rilyazine derivatives and compositions for the treatment of cancer” Warner, John C.; Gladding, Jeffery A.; Gero, Thomas W.; Cheruku, Srinivasa R. PCT Int. Appl. WO 2015034785. Filed August 29, 2014. Published March 12, 2015.

“Preparation of Rilyazine Derivatives Useful in Treatment of Cancer” Warner, John C.; Gladding, Jeffery A.; Gero, Thomas W.; Cheruku, Srinivasa R. US Pat. Appl. US 20150065510. Filed August 29, 2014. Published March 5, 2015.

Cytostats for Oncology

Rilyazine








Films and Coatings

AsphaltenesMaltenes

Maltenes undergo photo-oxidation to Asphaltenesmaking the pavement dryer and more brittle.

It was made by Joseph Nicéphore Niépce

This is world’s oldest known photograph made in 1825

He exposed a metal sheet coated with asphalt to light ina camera for 8 hours. The areas irradiated by light washed off!

Construction Materials: Asphalt Paving

“Asphalt Binder Additive Compositions and Related Materials” Warner, John C., Muollo, Laura R.; Walker, Rowan L., Bianchini, J. R. PCT Int. Appl. WO 2015070180. May 14, 2015.“Composition to Rejuvenate Asphalt” Warner, John C., Muollo, Laura R., Walker, Rowan L. US Pat Application No. 61/902,706, November 11, 2013.

> 50% Recycled Material < 20oF

Delta-S

November 25, 2013

Formaldehyde Free Wood Composites

“Lignocellulosic Compositions and Methods of Making Same” Warner, John C. et al. US Patent Filed








Films and Coatings

Hair Color Restoration

Tyrosinase

Tyrosinase

“Formulation and Processes for Hair Coloring” Warner, John C.; Muollo, Laura; Stewart, Amie. US Patent 8,828,100. Filed Oct. 14, 2013. Published September 9, 2014.

December 1st, 2015

Hair and Fabric Shaping and Toning

“Photoreactive Polymers and Devices for use in Hair Treatments” Warner, John C.; Cannon, Amy S.; Raudys, Jennifer; Undurti, Arundhati; PCT Int. Appl. WO 2004058187. Filed December 22, 2003. Published December 23, 2004. CA 2510162. Filed December 22, 2003. Published July 15, 2004. EP 1575537. Filed December 22, 2003. Published September 21, 2005.“Photoinduced Copolymer Functionalized Substrates” Warner, John C.; Cannon, Amy S.; Dye, Kevin PCT Int. Appl. WO 2007139810. Filed May 23, 2007. Published December 6, 2007.

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Films and Coatings

Flavor Enhancement

Bromine Free Flame Retardants

“Bromine-Free Fire Retardant (FR) Agents Capable of Using a Cyclization Mechanism” Warner, John; Tang, Pui-In; Stewart, Amie; Kelly, Colleen. PCT Int. Appl. WO 2015050542. Filed October 2, 2013. Published April 9, 2015.

“Structured endothermic fire-retardant agents encapsulated in thermally-sensitive material and fire-retardant composition comprising polymer matrix and microcapsules incorporating fire-retardant agents” Warner, John; Tang, Pui-Ln; Stewart, Amie; Kelly, Colleen. PCT Int. Appl. WO 2015026353. Filed August 22, 2013. Published February 26, 2015.


Films and Coatings






Films and Coatings

“Protective barriers for electronic devices” Warner, John C.; Viola, Michael S. US Patent 8,581,246. Filed September 2, 2011. Published November 12, 2013. “Dye-Sensitized Solar Cell and Corrosion Resistant Electrode Stack Therein” Plavisch, Lauren; Ricci, Melissa; Warner, John C. US Pat. Appl. US 20130263921. Filed April 10, 2012. Published October 10, 2013.“Solar Cells with a Colorant Sensitized Semiconductor Layer Prepared from a PresensitizedSemiconductor Composition” Warner, John C.; Viola, Michael S.; Barykina, Olga; Dua, Vineet. US Pat. Appl. US 20130180587. Filed January 17, 2012. Published July 18, 2013.“Dye Formulation for Fabricating Dye Sensitized Electronic Devices” Warner, John C.; Viola, Michael S., US Pat. Appl. US 20130074935. Filed September 23, 2011. Published March 28, 2013.“Systems and Methods for Preparing a Metal Oxide Based Anode for Dye-Sensitized Solar Cells” Warner, John C.; Van Benschoten, Helen; Cannon, Amy US Pat. Appl. US 20110232742. Filed Feb. 17, 2011. Published September 29, 2011.“Semiconductor Compositions for Dye-Sensitized Solar Cells” Warner, John C.; Vanbenschoten, Helen; Cannon, Amy US Pat. Appl. US 20110232717. Filed February 17, 2011. Published September 29, 2011.“Additives for Solar Cell Semiconductors” Warner, John C. US Pat. Appl. US 20110226306. Filed Feb. 17, 2011. Published September 22, 2011.“Systems and Methods for Preparing Components of Photovoltaic Cells” Warner, John C.; Van Benschoten, Helen; Cannon, Amy PCT Int. Appl. WO 2011103494. Filed February 18, 2011. Published August 25, 2011.“Semiconductor Compositions for Dye-Sensitized Solar Cells” Warner, John C.; Vanbenschoten, Helen; Cannon, Amy PCT Int. Appl. WO 2011103503. Filed February 18, 2011. Published August 25, 2011.“Additives for Solar Cell Semiconductors” Warner, John C. PCT Int. Appl. WO 2011103506. Filed February 18, 2011. Published August 25, 2011.“Metal Oxide Films” Warner, John C.; Morelli, Alessandra US Pat. Appl. US 20030054207. Filed July 17, 2002. Published March 20, 2003. PCT Int. Appl. WO 2003008079. Filed July 17, 2992. Published January 30, 2003.

Solar and Electronic Applications

BPA Free Thermal Printing

“Thermal Recording Media” Chakar, Fadi Selim; Warner, John Charles; Whitfield, Justin Robert; Lugus, Michelle Wanch Li; Banerjee, Deboshri, PCT Int. Appl. WO 2015094630 Published June 25, 2015.

“Thermal Recording Materials Containing Phosphate Modifier” Chakar, Fadi Selim; Warner, John Charles; Whitfield, Justin Robert; Lugus, Michelle Wanch Li; Banerjee, Deboshri, US Pat. Appl. US 20150165806. Filed December 18, 2013. Published June 18, 2015.

“Thermal Imaging” Warner, John C. US Pat. Appl. US 20140371064. Filed June 18, 2013. Published December 18, 2014.

"Thermographic Recording Films." Dombrowski, Edward J.; Jones, Robert L.; Warner, John C.; Yang, Jiyue US Patent 5,750,463. Filed April 22, 1997. Published May 12, 1998.








Films and Coatings

June 29, 2015

Ocean Plastics Recycling and Reclamation

“Method for the recovery of lithium cobalt oxide from lithium ion batteries” Poe, Sarah L.; Paradise, Christopher L.; Muollo, Laura R.; Pal, Reshma; Warner, John C.; Korzenski, Michael B. US Pat. Appl. US 20140306162. Filed June 19, 2012. Published October 16, 2014.

“Sustainable process for reclaiming precious metals and base metals from electronic waste” Korzenski, Michael B.; Jiang, Ping; Norman, James; Warner, John C.; Ingalls, Laura; Gnanamgari, Dinakar; Strickler, Fred; Mendum, Ted. US Pat. Appl. US 20130336857. Filed August 19, 2011. Published December 19, 2013.

“Sustainable process for reclaiming precious metals and base metals from electronic waste” Korzenski, Michael B.; Jiang, Ping; Norman, James; Warner, John C.; Ingalls, Laura; Gnanamgari, Dinakar; Strickler, Fred; Mendum, Ted. PCT Int. Appl. WO 2012024603. Filed August 19, 2011. Published February 23, 2013. CN 103249849. Filed August 19, 2011. Published August 14, 2013. EP 2606158. Filed August 19, 2011. Published June 26, 2013.

“Non-fluoride containing composition for removal of polymers and other organic material from a surface” Korzenski, Michael B.; Jiang, Ping; Warner, John C.; Mendum, Ted; Lugus, Michelle; Whitfield, Justin; Vanbenschoten, Helen; Payne, Makonnen PCT Int. Appl. WO 2010091045. Filed Feb 3, 2010. Published August 12, 2010.

Electronics Recycling and Reclamation

LiCoO2

Confidential - Warner Babcock Institute for Green Chemistry, LLC

Water Harvesting Technologies

Hydrophobic Hydrophilic

Innovation & Creativity

We are successful not IN SPITE of green chemistry

But BECAUSE of green chemistry

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Innovation to Commercialization: Case Studies · Paul Anastas Amy Cannon Julie Haack Jim Hutchison...

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