Eu tive um sonho ontem à noite

O Vencedor da Copa do Mundo é o Brasil

Alemanha

BRASIL

Argentina

Brasil !!!

Brasil !!

Brasil !!!

Idade da Pedra – 3.5 milhões de

anos atrás

A Idade da Pedra não acabou porque eles ficaram sem pedras

Agricultura. Isso levou à construção de assentamentos permanentes.

E para os excedentes, o que significa que nem todos tinham que ser

fazendeiros - algumas pessoas podiam se especializar em outras

coisas, como produzir melhores ferramentas. Isso também significava

comércio e troca de idéias. O comércio significava manter registros e

precisava de escrita e ciência. Tudo isso resultou em um grande

aumento da cultura e da tecnologia.

Foi quando alguém inventou a fundição do cobre e a adição de estanho

... bronze. A idade da pedra acabou e a idade do bronze começa.

A ciência é o núcleo da nossa própria existência. Todos os dias todo mundo utiliza a ciência. Sem isso, estaríamos

de volta à idade da pedra. Uma vez que a ciência é o assunto mais importante, é lógico concluir que uma palestra sobre ciência ou uma palestra científica deve

ter o mais alto grau de atenção do público

A sala está escura e a

voz solitária está dizendo

algo sobre a reologia em

nanoescala de um poli-

algo-ou-outro

Às vezes, a melhor cura para a insônia é uma apresentação científica

“Tente se divertir. Isso não

é para ser educativo ”.

1.3 billion

1.2 billion

Calcutta no período da manhã

As crianças nos EUA escutam

• Siga os seus sonhos

• Seja o que você quiser ser

• O fator mais importante para a

motivação é ter metas estabelecidas

Crescendo na Índia(com um qualificador omitido)

Siga os seus sonhossomente se você sonha em ser médico

Seja o que você quiser sersó se você quer ser engenheiro

O fator mais importante para a motivação

é ter metas estabelecidas

E é melhor você definir uma meta para estudar ciência e tecnologia

A cidade onde tudo vai bem ultimamente será a cidade onde nada vai bem

Greve e passeataMarcha Contra a Privatização e por Salários Mais justos

Paciência também é uma forma de ação

Sir Robert Ross, Nobel Prize in Medicine 1902

Amartya Sen, Nobel Prize in Economic Sciences 1998

C.V. Raman, Nobel Prize for Physics 1930 (Raman Spectra)

Mother Teresa, Noble Peace Prize 1979

Tagore, Nobel Prize in literature 1913

Cure for malaria

love and care for those persons nobody looked after

Nobel Laureates of Kolkata

Indo para o trabalho

Quando você começa a sentir o calor, você começa a ver a luz

Senator Everett Dirksen, IL

Corre Forest Corre

América é outro nome

para oportunidades

- Ralph Waldo Emerson

Golden Dome no inverno

Carbono, o denominador comum em

todos os seres vivos. Toda a vida como

a conhecemos é composta de

compostos orgânicos

Penicilina

Thomas Jefferson's Academic Village at the University of Virginia

A Rotunda da Universidade de Virginia

This research resulted in a development of new types of DNA intercalating agents, which could serve as anti-malarial, anti-leukemia and anti-parasitic agents.

Impact

1. J. Heterocycl.Chem., No. 22, p 129,1988

2. J. Med. Chem., Vol. 33, p 298, 1990

3. US 5204352, 1993

Hercules Incorporated1987-2002

Vendas anuais US $ 3,5 bilhões

Mais de 20.000 funcionários

Centro de Pesquisa tinha1100 pessoas, incluindo300 PhDs

Outros 200 PhDs emFábricas de manufatura

Divisões da Hercules

• Poliolefinas (incluindo PP e UHMW PE)

• Fibra

• Filme

• Orgânicos (incluindo resinas e peróxidos)

• Papel

• Produtos eletrônicos

• Borracha

• Gerência de água

• Química-Mineração

• Aqualon (celulósico, guar)

• Revestimentos

• Aeroespacial

• Materiais avançados (fibra de carbono, compósitos)

• Gomas Alimentares

• Ingredientes de fragrância e sabor

• Explosivos

Polyphenylene oxide polymer

Usos especiais da soja

Algumas pessoas chamam a soja de uma cultura

miraculosa porque a soja é usada como alimento para

pessoas, como ração animal e em mais de 140 produtos

não alimentícios como combustível, tinta, cola e

maquiagem.

Soybean field & enlarged soybean

• Farmers in China grew soybeans some 5,000 years ago!

• The first soybeans were brought to the U.S. on a Yankee clipper in 1804 in the early days of our nation.

• Just after the turn of the century, in 1904, George Washington Carver began studying the soybean at the Tuskegee Institute in Alabama. People no longer thought of the soybean as just a feed crop, but also as a source of protein and oil.

US Crop Area

Planted. 2016

Soybean production in Brazil

"Cash soybean price in my town is 74 real per bag

($10 per bushel) this week, compared to 65 reals per

bag ($8.67 per bushel) one month ago, an increase

of 14% in one month."

Carlos Alberto is the general marketing director of CooperFibra, a farmers' cooperative with 185 members farming 140,000 hectares (almost 346,000 acres) of soybean crop. He told DTN in mid-April.

- Carlos Alberto

Brazil’s top 10 exports in 2017

• Soybeans: $25.7 billion (up 33% since 2016)• Iron ores, slag, ash: $22.4 billion (10.3%)

• Mineral fuels including oil: $18.7 billion (8.6%)

• Vehicles : $14.7 billion (6.8%)

• Meat: $14 billion (6.4%)

• Machinery including computers: $13.8 billion (6.4%)

• Sugar, sugar confectionery: $11.6 billion (5.3%)

• Iron, steel: $10.8 billion (4.9%)

• Woodpulp: $6.4 billion (2.9%)

• Food industry waste, animal fodder: $5.4 billion (2.5%)

U.S. Soybean Area Planted, 1987-2016

De acordo com a Oil World, a produção brasileira de

óleo de soja em 2017 - 2018 atingirá uma alta de 5

anos, com 8,57 milhões de toneladas

Pesquisa em Alimentos

Pesquisa direcionada para aplicações em soja

Outras áreas de pesquisa

Para dar uma visão geral de pesquisas

recentes sobre aplicações não-

alimentares de soja, falarei sobre o

trabalho de outros cientistas. Depois

disso, vou me concentrar em três

projetos em detalhes.

Lamento que você tenha que tolerar meu

sotaque e minha fala rápida.

Cost Effective Polyols from Soybean Oil for Foams, Cast Resins and Sealants

Jian Hong, Zoran Petrovic

Kansas Polymer Research Center

Pittsburg State University, Pittsburg, KS

66

Strategy

8

Chemical

modification

http://www.oil-press-machine.com/Solution/oil_plants_solutions/soybean-oil-press.html

Polyol

OH

OH

HO

Isocyanate

OCN-R-NCO

Polyurethane

Soybean oil

Cast sheet

Make foam

Sealant

High Oleic Soy Hydrophobic Latex and

Coatings

Jingyi Xie, Wumin Yu, Daniel Nicklas, Joseph Ferguson

Woodcare R&D, Rust-Oleum Corporation

Water Damage to Architecture Materials

Rot

Water

Freeze-thaw

damage

RustDelamination

69

Rust-Oleum Platforms and BrandsSmall ProjectPaints

Cleaners Primers & Roofing

SpecialtyProducts High PerformanceCoatings

Interior WoodCareCraft & Hobby

Automotive &Removers Exterior WoodCare

70

HOSO vs. Traditional Soy Oil

Traditional soybean oil (SO)

Pentadiene structure

High oleic soybean oil (HOSO)

71

Reactive Intermediate

HOSO based acrylic monomer

Our approach to HOSO Based Hydrophobic

Latex SynthesisReactive group

Latex

72

Advantages of Hydrophobic Latex

Cost competitive

Low VOC

Compatibility

Easy toapply

Widely application

73

Potential Soybean Consumption

74

• Based on 2015 data for US exterior coating (9.04 billion)

• 5% share of latex is used for exterior coating (450 million

pounds)

• Soya acrylic monomer incorporation rate >10%

• Soy oil content in soya acrylic monomer ≈75%

• Overall consumption of soybean ≈ 1.4 million bushels/yr

• More consumption due to other applications or growth of

market

Demonstration of Soy-Based Thermoplastics for Adhesives and Asphalt Modification

Where the (Bio)Rubber Meets the Road

Eric W. Cochran | Dr. Christopher Williams - Iowa State University

Don Sjogren - ArgoGenesis Chemical, LLC and Seneca Petroleum

Brian Majeska & Joe Lorenc - Adventus Material Strategies,LLC

Acrylated Epoxidized Soybean OilRAFT polymerization allows high conversion withoutgelation

USB TAPMEETINGIntroduction – WhyTPEs? USB TAPMEETING

Our Strategy

Soybeanoil Intermediates Plastics & Resins Applications

Functionalitynumber

ranges from 1.0 ~2.6

How reaction conditionseffect

reaction rate, mass yield and

etc

USB TAPMEETINGApplications USB TAPMEETING

Soy Based Alkyd Technology Platform for

Lower VOC Wood Coatings and Stains

Wumin Yu, Joseph FergusonWoodcare R&D, Rust-Oleum Corporation

Soy-based Low VOC Technology Platform

Soybean oil

Wood finishes

Soy reactive diluents (VOCreducer)

Wood stains Wood preservatives

79

O

O

O

O O

Synthesis of Novel Soy Reactive DiluentO

Soybeanoil

O

N H

HO

O

HO

O

O

O

+Ethanolamine

Functional soy

intermediate

H2N OH

80

Comparable Color Strength

Old tinting New tinting Old tinting New tinting

Based on 90 wt% of neutral base and 10 wt% of tinting

81

Better Anti-Skinning Performance

OldTinting NewTinting

82

Summary

83

• A novel soy reactive diluent* for solvent-based low

VOC stains and tinting pastes

- 250 VOC, same fast recoat time as 550 VOC fast dry

stain

- High soy content and cost competitive

- Rich color and excellent wetting and penetration

- Zero VOC, cost competitive tint pastes for solvent-based

stains* U.S. Patent Application Serial No.62/307652

Synthesis of Novel Soy Reactive Diluent+ Multifunctional molecule

Soyreactive

diluent

U.S. Pat. Appl.No.

62/307652

84

Developing soybean oil-based alternative coating materials

T. Wang, T. Fei, and D. Jarboe

Iowa State Univ

Developing powder coating resin using HOSO

Good hardness High

melting pointHardness not as good

High melting point

① ②

High hardness

Scratch resistance

Higher hardness, glossy

Better scratch resistanc

• Global powder coatings will

reach $12.53 billion in 2020

(Frost and Sullivan);

• But, the challenge is

shortage of raw materials;

• Bio-based resin (mostly

derived from citric acid,

isosorbide, and succinic acid)

has low Tg, yellows, and does

not weather well;

• Different HOSO-based resins

are being developed

• Problems:

• Tackiness

• Significant darkening

after curing

New High Oleic Soybean Oil

(HOSO)-Based Latexes for

Coatings and Paints

www.qualisoy.com https://www.agprofessional.com/

Andriy Voronov

Coatings and Polymeric Materials

North Dakota State University

andriy.voronov@ndsu.edu

https://cpmvoronov.wordpress.com/

1

Synthesis of Soy Oil-Based Monomers

Transesterification reaction of oil and N-(hydroxyalkyl)acrylamide

I.Tarnavchyk, A. Voronov, Bio-based Acrylic Monomers and Polymers Thereof , U.S. Patent Application

044 288, August 7,2015

Dr. Ihor Tarnavchyk

90

Summary

91

Exemplified for soybean (SBM), high-oleic soybean oil (HO-SBM) one-step

transesterification of triglycerides into monomer for free radical

polymerization

SBM and HO-SBM undergo chain propagation in free radical

polymerization, also act as retarders by chain transfer reaction, which

depends on a amount of unsaturation

SBM and HO-SBM are reactive in chain copolymerization with petroleum-

based counterparts. Soy oil-based fragments provide plasticizing and

hydrophobizing effects to latex films

I.Tarnavchyk et al. ACS Sustainable Chemistry & Engineering, 2015, 3(7), 1618 - 1622

Z.Demchuk et al. ACS Sustainable Chemistry & Engineering, 2016, 4(12), 6974 - 6980

Z.Demchuk, et al. ACS Omega, 2016, 1(6), 1374 - 1382K.Kingsley , et al. Industrial Crops and Products, 2017, 109, 274-280

Z.Demchuk et al. ACS Sustainable Chemistry & Engineering, 2018, 6 (2), 2870 – 2876.

Acrylic Latex Paints

92

The Illinois Heartland is at the center of high yield soybean production

National Center for Agricultural Utilization Research (NCAUR/USDA)

U.S. Soybean Crop Value,

1987-2016

Novel Nitrogen-Containing Products Derived from Soy Bean Oil (SBO)

Dr. Atanu Biswas

National Center for Agricultural Utilization Research

U.S. Department of Agriculture

Peoria, IL

• At USDA we have discovered several new ways to make new products from it

• Three examples will be shown• Self-curing product• Additive for lubricating oil• Potential carrier for fragrance or drugs

• These are products of green chemistry• Friendly process. No solvent is needed

First Product: Self-Curing Adhesive

• We discovered a new process that permits SBO to be reactive

• It takes advantage of the “ene reaction”

• The formulation is self-curing over time• The product may have applications as an adhesive,

cement, or sealant

• The reaction is amenable to scale-up• No solvent is needed• Low energy requirement

Reaction with SBO-Double Bond

Biswas et. al., Green Chemistry, 9(1):85-89. 2007Biswas et. al., Green Chemistry, 10(1):298-303. 2008

oiloiloil

Adhesive and Sealant Application

• Global market for adhesives and sealants is 15.2 billion lbs per year

• A promising area involves medical use– $1.3 billion in the U.S., with 7.5% annual growth– Use in sutures and staples (medical) and pit and fissure sealants

(dental)– Some current products are based on acrylics– SBO is more environmentally friendly, less toxic, and more compatible

with human body

• If we can capture 1% of that business, that would be $13 MM per year

• More work is needed to develop an alternative for DEAD

Second Product: Additive for Lubricating Oil

• We discovered another process that permits SBO to be reactive

• We start with epoxidized SBO and uses “amination” reaction

• We can make the epoxidized SBO ourselves or purchase it• It is commercially available

• We can graft different structures to SBO• Some structures may be used as lubricant additive

• The advantage is higher resistance toward heat, oxidation, and aging

Synthesis of an Amine-Oleate Derivative using an Ionic Catalyst

Biswas et. al., US Patent 8841470, 2014

Biswas et. al., Journal of Agricultural and Food Chemistry. 57(1):8136-8141. 2009

Biswas et. al., Journal of Agricultural and Food Chemistry. 56(14):5611-5616. 2008

O

O

CH3

CH3

O

NH

OCH3

O

NH2

+60-105 °C

1-Me-Imidazoline tetrafluoroborate catalyst

XX

O

O

CH3

CH3

NHOH

Isomer B

O

O

CH3

CH3

NH OH

Isomer A

+

Lubricant Application

• U.S. market for lubricants is $13.4 billion per year• Growth rate ~ 4% per year• Big players include Shell, Exxon Mobil, and Chevron

• Lubricants are commodities, but additives for lubricants have higher value

• BHT antioxidant price ~ $1.80 per lb

• USDA work product is novel• Patent has been issued• More work is needed to develop guiding cost and evaluate

profitability

Third Product: Carriers for personal care products or pharmaceuticals

• The same chemistry can be used in other ways• One method is to graft phenyl, pyridine, and/or amide-

containing functionality to soybean oil

• These functionalities can bind with fragrance or drug ingredients

• The modified SBO can be a convenient carrier for sunscreen, emollient, fragrance, or drug molecules

• Applications can be sought in personal care or in pharmaceuticals

• SBO is easy to use on skin, non-toxic, and cheap

De plantas a plásticos

Atanu Biswas

NCAUR

Peoria, IL

Se você rouba ideias de um autor, é plágio; se você rouba

de muitos, é pesquisa

Wilson Mizner

O

OAcAcO

OAc

OO

OAcAcO

OAc

[ ]n

O

OHOH

OH

OO

OHOH

OH

[ ]n

I2

Ac2O

Discovery of Iodine-Catalyzed Acylation of Polysaccharides

Cellulose or starch Cellulose acetate or starch acetate

Biswas, et al , Biomacromolecules, 6,1843-1845 (2005)

Cellulose Esters Have

Attractive Physical Properties

Cellulose Acetate Propionate (CAP)

• Plastics - toothbrushes, tool handles, ophthalmic / frames

• Inks / specialty coatings

Cellulose Acetate Butyrate (CAB)

• Plastics - brush and tool handles, pen barrels, profiles, Uvex™ sheet

• Coatings - automotive OEM and refinish, wood furniture, leather

• Film - optical polarizing sheet

Functionalized Cellulose Esters

• Controlled-release coatings (C-A-P)

• Radiation cure coatings (CAP-UV100)

Chemistry is magic

Biodiesel Work

Gerhard Knothe

USDA / ARS / NCAUR

Biodiesel Production in the United States

2006 2007 2008 2009 2011 2012 2013 2014 20162010 2015

0

500

1000

1500

2000

2500

3000

3500

4000M

illio

ns o

f ga

llons

Year

250

450

700545

315

1147 1160

1985 19762093

2890

Europe: 3473

• Data for biodiesel and renewable diesel (hydrocarbons from thesame feedstocks).

Why biodiesel and not the neat oil?

CH2-OOCR1 R׳OOCR1 CH2OH| Catalyst | CH-OOCR2 + 3 R׳OH → R׳OOCR2 + CHOH

| |CH2-OOCR3 R׳OOCR3 CH2OH

Vegetable (Other) Oil Alcohol Vegetable Oil Alkyl Esters Glycerol (Triacylglycerol) (Biodiesel)

Viscosity!

27-35 mm2/sec (40°C) 4-5 mm2/sec (40°C)

• Kinematic viscosity of petrodiesel fuels usually ≈ 1.8-3.0 mm2/sec (40°C).

• Lower viscosity of biodiesel vs. vegetable oil reduces engine deposits.

Advantages of Biodiesel

• Renewable fuel of domestic origin - largely CO2 neutral

• Technically competitive with petrodiesel;

• Miscible with petrodiesel in all ratios

• Largely compatible with the existing infrastructure

• Environmental benefits

• Biodegradability

• Most regulated exhaust emissions reduced

• Safer handling (higher flash point)

• Inherent lubricity

• Blending with low-lubricity ultra low sulfur petrodiesel to

impart lubricity

• Low or no sulfur / aromatics

• Positive energy balance (> 4:1)

Technical and Other Problems with Biodiesel; Focus of NCAUR Research

• Cold flow

• Some components of biodiesel have high melting points.

• Oxidative / storage stability

• Some components of biodiesel can oxidize in contact with air.

• Nitrogen oxides (NOx) exhaust emissions

• May fade with time due to new exhaust emissions

control technologies.

• Other fuel quality issues

• Minor components influencing fuel properties.

• “Designer” Biodiesel

• Modifying biodiesel composition to improve properties.

• Feedstocks

• Increase supply of biodiesel with acceptable properties.

GOODYEAR CONFIDENTIAL

Soybean Oil as a Replacement

for Petroleum-based Oils in Oil

Extended Tire Tread

Compounds

Why SoybeanOil?

GOODYEAR CONFIDENTIAL

•The use of soybean oil in place of petroleum-based oils is

appealing as soybean oil is:

– Domestic, abundant and renewable

– Possesses key attributes required of extender oils

• Chemical and physical compatibility with rubber matrix

• Low and high temperature behavior (thermal stability)

•The “Green” movement towards renewable materials and

increased fuel efficiency is a growing industry trend

•Unique properties of soybean oil can be leveraged to

provide performance and/or processing benefits

•Consistent with Goodyear’s commitment to being an

“Innovation Leader” in the industry

– Competitively advantaged; profitable through economic cycles

Soybean Oil vs. Current ProcessOils

•MES oils replace DAE oils

•Less compatible with rubber

•Compound adjustments

possible

•Various grades available

GOODYEAR CONFIDENTIAL

•Domestic, renewableresource

• Compound adjustmentspossible

• Various gradesavailable

•DAE oils have long been used

in tires

•Excellent compatibility

•Phased out of Goodyear tire

production

Current Drivers for TireTechnology

•Wet Performance

•Increased fuelefficiency

•Increased mileage

•TireLabeling

•Sustainability

GOODYEAR CONFIDENTIAL

Tire Technology PerformanceTriangle

Rolling

Resistanc

e

Wet /Dry

Performanc

e

Treadwear

100

110

120

130

100

120140

160

100

105110

115

GOODYEAR CONFIDENTIAL

•Key tire performance

attributes make-up the

“Performance Triangle”

•Performance “trade-offs”

can occur when

improving one attribute

•High performance

polymers

may minimize “trade-offs”

•High performance

polymers and tread

compounds are often

more difficult to process

Initial Approach – “Drop-In” Replacement

•Direct replacement of heavy naphthenic (MES)

extender oil with SBO in a current commercial SSBR

•Replacement of MES oil with SBO shifted the Glass

Transition Temperature (Tg) of the extended polymer

and subsequent compound, impacting the Wet/RR

balance

0

50

100

150

Processing

Cure Rate, T25

Wet traction

Dry handling

Stress/Strain

Rolling resistance

Wear

Tear

SBOSSBR

MES SSBR

GOODYEAR CONFIDENTIAL

Compound Adjustments – Polymer Ratio

•The Tg of a tread compound dictates the Wet/RR

performance balance

•Polymer blend (SSBR/cis-PBD) in SBO compound adjusted

to match Tg

0.1

0

0.2

0.3

0.4

0.5

0.6

0.7

-100 -80 -60 -40 20 40 60 80-20 0

Temp (C)

Ta

nD

elt

a

Soy Oil SSBR

MES Oil SSBR

Wet

Traction

SSBR/PBD

Ratio SBO

SSBR = HIGH

MES SSBR =

LOW

Control SBO TireOil MES SBO

Oil phr 37.5 20

Coupler Si Si

OE Tg -37 °C -47 °C

SSBR/PBD Ratio Low High

Tire Performance Test Results (Normalized)

Rolling Resistance 100 103

Treadwear 100 90

Wet Braking 100 101

Wet TractionTest 100 102

Wet Handling 100 104

Dry Braking 100 99

Dry TractionTest 100 102

Max DryHandling 100 98

Subjective Handling 100 98

SBO-Extended PolymerDevelopment

GOODYEAR CONFIDENTIAL

•Development of new polymer microstructure to

accommodate SBO

– Allow for direct comparison of SBO and MES oil absent

significant compound adjustments

•SBO-extended SSBR is advantageous compared to free

SBO addition

– Reduces plant complexity

– Potential for family of SBO-extended SSBRs to support

Goodyear

SBO-extended SSBR in New ProductDevelopment

• In general, the low Tg of

SBO provides performance

benefits at low

temperatures

•We hypothesized that the

combination of a high Tg

polymer with the low Tg

SBO could further

alleviate the typical

wet/winter tradeoffs

•Released SBO-extended SSBR

was targeted for use in a new

passenger tire product

The SBO-extended SSBR has been commercialized and is used in the

Assurance WeatherReady tireGOODYEAR CONFIDENTIAL

Petroleum-

based OilSoybean Oil

Rolling Resistance 100% 103%

Wet Performance Testing

Wet Braking 100% 96%

Wet Grip 100% 95%

Wet Traction Test 100% 95%

Wet Handling 100% 99%

Dry Performance Testing

Dry Handling 100% 98%

Dry Braking 100% 99%

Winter Performance Testing

Snow Traction 100% 111%

Ice Traction 100% 105%

Processing (Mixing) 100% 108%

Assurance WeatherReady Tire

•Goodyear has successfully developed an innovative new

soy- based rubber tread compound for use in the Assurance

WeatherReady Tire

•The soy-based compound remains flexible at lower

temperatures, providing improved traction in all weather

conditions

•The total petroleum oil content has been reduced by up to

60%

GOODYEAR CONFIDENTIAL

Environmental Achievement of theYear

• Goodyear’s Soybean Oil Initiative won TireTechnology

International’s “Environmental Achievement of theYear”

GOODYEAR CONFIDENTIAL

Eagle EnforcerAll-Weather

• Goodyear has introduced the Eagle Enforcer All-Weather

tire for police pursuit vehicles, which contains soybean

oil in the tread.

GOODYEAR CONFIDENTIAL

Summary and FutureDirections

GOODYEAR CONFIDENTIAL

• Goodyear has commercialized two new tire

products containing soybean oil

• The unique properties of soybean oil were

leveraged to meet challenging performance

goals

• Efforts to expand this technology into

additional product lines remain ongoing

• Securing intellectual property for new ideas is

a priority in 2018, along with evaluating

soybean oil in light truck applications

Thankyou!

The Goodyear Tire & Rubber Company would like

to thank the United Soybean Board for generously

supporting our research activities since 2011

GOODYEAR CONFIDENTIAL

A Estolides

Steven C. Cermak,

and

Terry A. Isbell

USDA/ARS/NCAUR

1815 N. University St.

Peoria, IL 61604

O

O

O

O

O

O

Vegetable Oil

• Good Lubricity

• Good Biodegradability

• High Pour and Cloud Points and Bad Low Temperature Storage

• Poor Oxidative Stability

• Relative High Cost Compared to Mineral Oils

Triglyceride FattyAcid

Estolide Ester

142

Estolide Structure

Estolides are a class of compounds derived from the

oligomerization of fatty acids. Estolides are known for their high--

‐performance in lubricant formulations, and are ideal fluids for

environmentally acceptable lubricant (EAL) applications.

• Estolides are oligomeric esters

– Reducing unsaturation improves oxidative stability

– Molecular branching improves cold temperature properties

• The secondary ester makes the molecule more resistant to water hydrolysis

• Vegetable based estolides, with high molecular weight and good lubricity, yield lower evaporative loss values compared to similar viscosity grade oils

• Vegetable oils estolides maintain low coefficient of friction and good lubricity characteristics

• The ester linkages in the estolide molecule make it readily biodegradable

• Estolide viscosity can be tailored across a wide range with

carboxylic ester functionality and degree of oligermizationIsbell, Terry A.; Cermak, Steven C. Estolides: A Developing & Versatile Lubricant Base Stock.

Society of Tribologists and Lubrication Engineers newsletter January 01, 2014.

ESTOLIDES

-40

-30

-20

-10

0

Pour Point Comparison of Mineral Oil Based Motor Oils to Estolides

Po

ur

Po

int

(oC

)

Pe

nzo

il5

W-3

0

Ole

ic-L

aura

te

Esto

lide

Ole

ic-C

oco

Esto

lide

Val

volin

e S

AE-

30

Val

volin

e 5

W-3

0

Ole

ic E

sto

lide

Val

volin

e 1

0W

-30

Mo

bil

10

W-3

0

Mo

bil

10

W-4

0

Val

volin

e 1

0W

-40

Val

volin

e 2

0W

-50

Bio

Soy

SoyL

ink

INDUSTRIAL LUBRICANT MARKET

TOTAL ANNUAL USAGE

With a 1.0% share of the global base oil market (expected in 2016), revenue will exceed $850 million with EBITDA of over $65 million. (105 million gallons @ 8.25/gal)

Performance Benefit

High oxidative

stability

Increased oil longevity

Low volatility Low evaporation rates

Safer in high temperature applications

High viscosity

index

Minimizes change in viscosity with temperature

change

Less viscosity modifier required

Excellent

hydrolytic stability

Increased oil longevity

Good for applications with risk of water

contamination

Natural

detergency

Keeps equipment looking clean and new

Biodegradability Rapidly breaks down once released into the

environment

Bio content Made from renewable carbon

Reduce dependence on petroleum products

ESTOLIDES FOR HIGH PERFORMANCE MOTOR OILS

Engine CleanlinessField Trial Details

• 150,000 mile (241,402 km) taxi cab field trial under severe stop

and go conditions in Las Vegas Nevada, USA

• First 100,000 miles (160,934 km) ≈ 84% estolide with additives

• Last 50,000 miles (80,467 km) ≈ 42% estolides, 42% GpIII, and

additives

• Reference Oil – Minimum Quality GF-5 oil

• Typical drain interval 2 to 3 times recommended mileage

• Vehicle – Taxi Cab, Chevy Impala, 3.5 liter V6

• Engines run on estolide-based formulations had far less

varnish

RESULTS FROM INDEPENDENT FIELD TRIALS DEMONSTRATE SUPERIOR PERFORMANCE

Motor Oil Field TrialExample

Conclusion:The Biosynthetic product

demonstrated an excellent ability to

reduce sludge and varnish,

resulting in improved fuel

economy, and longer lasting

engines.

Taxi engine after 150,000 miles using petroleum-

based oil (clear signs of varnish)

Taxi engine after 150,000 miles using Biosynthetic base oil

blend (little or no varnish)

In a 150,000 mile taxi cab field trial in Las Vegas, led by Infineum (ExxonMobil/Shell

subsidiary), our biosynthetic-based motor oil kept engines cleaner than

petroleum-based oils

13

ROBUST IP PORTFOLIO PROTECTS PRODUCTS, PROCESSES, AND APPLICATIONS

Upstream

Downstream

Oleic-based

Estolide molecules

Non-oleic based

Estolide molecules

Catalysts

for Estolide synthesis

Continuous and semi-

continuous Estolide

production process

By-products

from Estolide synthesis

Varying Estolide

viscosity grades

Estolide end product

formulations

Estolide end product

applications

Patents: 42 issued U.S. patents

• 7 issued Int’l patents

• 2 licensed U.S. patents (from

USDA)

• 21 pending U.S. patent

applications

• 62 pending Int’l applications

• All company IP expires after

2032

Patent portfolio creates a broad

and deep barrier to entry,

protecting the company and our

customers

All IP owned exclusively by BT

Proprietary and Confidential

Original Technology Invented and Patented by the USDA

OUR BROAD PATENT PORTFOLIO INCLUDES VARIATIONS OF OUR BIO-BASED MOLECULE

THAT CAN BE USED IN OTHER INDUSTRIES AND PRODUCT CATEGORIES

CocoEstolide™ is a Biosynthetic Base Oil that

is being tested for use in skin care, decorative

cosmetics and hair care

Superior shelf life (up to 10x)

Long lasting moisturization

Improves skin barrier function

Fast absorption and increased shine

Non-allergenic

Personal Care: JDA or Licensing Opportunity

Plastics, Paints, Coatings, Food IngredientsProcess Oils: Rubber and Other Sectors

Working with one of the world’s largest tire

manufacturers using Biosynthetic process oil in tires

Global demand for process oils in rubber is over 3 mil.

MT/yr.

1% mkt share in rubber = 30,000 MT

Process oils used in sectors other than rubber =

3.6 mil. MT/yr.

Proprietary and Confidential

Product Development Partnerships

Working with one of the world’s largest oil

companies to develop a low-viscosity

Biosynthetic base oil

Working with one of the world’s largest grease

manufacturers to create a high-viscosity

Biosynthetic base oil

While we will focus sales efforts initially on

the lubricant market, we will also be

seeking licensing and joint development

partnerships to enter other industries, such

as personal care, paints & coatings, and

food ingredients

APPLICATIONS FOR OUR PRODUCTS

• Cosmetics

• Emollients

• OtherProducts

• HydraulicOil

• Grease

• Gear Oil

• Trunk Piston Oil

• Cylinder Oil

•Process Oil

•Hydraulic Oil

•Compressor

Fluid

•Grease

•Metalworking Fluid

• Passenger Car Motor Oil

• Truck EngineOil

• Scooter/Motorcycle Oil

• Transmission Fluid

• Gear Oil

• Grease

Automotive Industrial

PersonalCare

Marine

ENVIRONMENTAL & SOCIAL BENEFITS

BP’s 2010 Deepwater Horizon costs US $62 billion

65.3

89.5

0 10 20 30 40 80 90 100

SE15B

SE7B

50 60 70

% Biodegraded in 28Days

Biosynthetic Base Oil - OECD 301B Ready Biodegradability Test

OUR BASE OILS PROVIDE ADDITIONAL ENVIRONMENTAL BENEFITS

Proprietary and Confidential

EnvironmentalBenefits

Biodegradability Rapidly breaks down once released into the environment

Bioaccumulation Does not accumulate in the tissues of livingorganisms

Toxicity Non-toxic by recognized OECD testing standards

Bio-content 80% to 90% from renewable carbonsources

BT BaseOils(WithoutAdditives)

Even after use, our oils are biodegradable and less toxic than petroleum.

Huge Market Opportunity

$30 Billion global lubricants industry – use as stand-alone base oil or blend

additive

Total capacity for three planned plants together is less than 3/10 of 1% of the globalmarket demand

Additional uses for personal care, food and specialty chemicals industries

Compelling Unit Economics: Low Cost Producer of High Performance Oils

Lower COGS than petroleum-based synthetic oils – competitive advantage

Superior Performance and Competitive Pricing . . . with Environmental

Benefits

Product performance validated in third-party field trials and customer testing

High oxidative and thermal stability; excellent hydrolytic stability, viscosity index; highflash point

High bio-based content and biodegradability; low toxicity and bioaccumulation; renewable, sustainable feedstock

Efficient, Readily Scalable Manufacturing Processes

SUMMARY OF PROJECT CONSIDERATIONS

Robust IP: Proprietary and patented processes, products, applications - 49 patents

issued, 83 pending

Efficient, continuous-flow processes use readily available feedstock and standard chemical processing equipment

Regulatory approvals and initial certifications in placeProprietary and Confidential

While working with Hercules, I established a Indian

music record level, Biswas Records. It was first of its

kind and for 10 years it was the largest Indian music

level outside of India. I have produced more than 200

compact discs (CD) and 10 DVD titles for Indian

music s and films. Now, due to technological

advancement, the CD/DVDs are becoming obsolete.

Biswas Records

Cientistas e Artistas

Leonardo, o cientista, e Leonardo, o artista, eram

um homem, não dois. Muitas das qualidades de

um cientista de sucesso e de um artista

talentoso são as mesmas:

Criatividade

Intuição

A vontade de jogar fora as regras

Observação direta da natureza

Capacidade de ver exemplos onde os outros vêem o caos

Politically correct race-neutral palm

Para mim o brasil é sinônimo de boa sorte

Em janeiro de 2014, o governo brasileiro concedeu ao Dr. Atanu

Biswas and Dr. Roselayne F. Furtado, Embrapa, Fortaleza a bolsa

"Ciência sem Fronteiras" para liderar pesquisas colaborativas

com grupos de pesquisa da Embrapa e visitar Fortaleza por 4

anos para trabalhar nas aplicações de biopolímeros em

embalagens, revestimentos, encapsulamentos de alimentos e

biossensores.

O Dr. Biswas foi o primeiro cientista do Serviço de Pesquisa

Agrícola (ARS) do USDA selecionado para participar deste

competitivo programa. Essa colaboração foi mutuamente benéfica

e facilitou os esforços de pesquisa sinérgica nos EUA e no Brasil

para resolver problemas técnicos regionais e globais.

Science without Borders Award

Biopolymers

Embrapa, Fortaleza

With Dr. Roselayne F. Furtado

If you have an apple, I have an apple, and we exchange these apples then you and I will still each have one apple. However, if you have an idea, I have an idea, and we exchange these ideas, then each of us will have two ideas.

George Bernard Shaw

Is it possible for world's top

two soybean producing

countries, Brazil and US to

collaborate in research?

Acknowledgement

Janet Berfield

Post doc Nuch

Megan Buttrum

Adriane C. Correa

HN Cheng Analia Veronica Gomez

I would like to thank Drs. Alexandre Jose Cattelan,

Fernando Henning, Embrapa scientists and all other

team members to organize such a great event.

Acknowledgement

Obrigadopela atenção

The End