natural, sustainable innovation: l’oréal’s …€œnatural, sustainable innovation:...
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2/16/2017
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gcande.org 9
• Sustainable Chemicals
• Flexible Chemical
Manufacturing
• More Efficient Processes
• Green Chemistry Curricula
• Circular Economy
Considerations
• Sustainable Materials
• Academic-Industry
Collaborations
• Chemicals Policy
• Cosmetics
• And More!
Early Bird Registration will be open from February 15 until April 28, 2017
www.acs.org/greenchemistry 10
ACS Green Chemistry Institute®
Engaging you to reimagine chemistry and engineering for a sustainable future.
We believe sustainable and green chemistry innovation holds the key to solving most environmental and human health issues facing our world today.
• Advancing Science • Advocating for Education • Accelerating Industry
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ACS GCI Industrial Roundtables
Catalyzing the integration of sustainable and green chemistry and engineering throughout the global chemistry
enterprise.
Including companies in the
cosmetics industry.
We convene 40 companies from across the world to focus on the science of sustainable and green
chemistry and its implementation.
We convene 40 companies from across the world to focus on the science of sustainable and green
chemistry and its implementation.
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Upcoming ACS Webinars www.acs.org/acswebinars
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Thursday, February 23, 2017
Fighting Cancer: Epigenetic Targets for Oncology Session 2 of the 2017 Drug Design and Delivery Symposium
Stuart Conway, Professor of Organic Chemistry, University of Oxford Sharan Bagal, Senior Medicinal Chemist, AstraZeneca
Thursday, March 2, 2017
TERA-print: From Academic Discovery to a Commercial Desktop Fab Session 2 of the 2017 Industrial Science Series
Chad Mirkin, Director, International Institute for Nanotechnology Mark Jones, Executive External Strategy and Communications Fellow, Dow Chemical
14
“Natural, Sustainable Innovation: L’Oréal’s Commitment to Renewable Materials and Eco-Friendly Processes”
www.acs.org/acswebinars
Slides available now! Recordings will be available once they are posted.
Michel Philippe L’Oréal Fellow,
L’Oréal
David Constable Science Director,
Green Chemistry Institute,
The American Chemical Society
Xavier Marat Group Leader,
Advanced Research, L’Oréal
This ACS Webinar is being co-produced by the ACS Green Chemistry Institute
2/16/2017
8
NATURAL, SUSTAINABLE INNOVATION:
L’ORÉAL’S COMMITMENT TO RENEWABLE
MATERIALS & ECO-FRIENDLY PROCESSES
Michel PHILIPPE, PhD and Xavier MARAT, PhD - L’Oréal R&I
25.8 Billions € (2016)
countries
people
International brands
205 Products sold every second
140
82,900
32
1st WORLDWIDE COSMETIC GROUP
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Hair dye Perfume
Make up Hair care Skincare
ALL THE BEAUTY NEEDS
17
18
About how many patents does L'Oreal hold?
• Almost 250 patents
• Almost 300 patents
• Almost 425 patents
• Almost 500 patents
• Almost 750 patents
Audience Survey Question ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT
2/16/2017
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3,870 people
497 patents 794M € (2015)
624
2011
582
2010
539
2009
523
2008
680
2012
748
2013
761
2014
RESEARCH & INNOVATION
19
20
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I N N OVAT I N G SUSTAINABLY
DEVELOPPING SUSTAINABLY
P RO D U C I N G SUSTAINABLY
L I V I N G SUSTAINABLY
21
INNOVATING SUSTAINABLY
BY 2020, WE WILL INNOVATE SO THAT 100% OF OUR PRODUCTS HAVE AN ENVIRONMENTAL OR SOCIAL BENEFIT.
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INNOVATING SUSTAINABLY
• the new formula REDUCES THE ENVIRONMENTAL FOOTPRINT
• the new formula uses RENEWABLE RAW MATERIALS SUSTAINABLY SOURCED or raw materials derived from GREEN CHEMISTRY
• the new packaging has an IMPROVED environmental profile
• the new product has an ENVIRONMENTAL or SOCIAL POSITIVE IMPACT
23
ECO-DESIGN APPROACH
24 24
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L'Oréal has implemented
Green Chemistry Principles for Many Years
http://youtu.be/QOi3ja1TaDo L’Oréal commitment to Green Chemistry 25
COMMITMENT TO GREEN
& SUSTAINABLE TRANSFORMATIONS
Safe by Design
to ensure maximum human and environmental health / safety
To develop innovation
From our internal Chemistry
And from Suppliers
Following the basic GREEN CHEMISTRY principles, published by P. T. Anastas and J.C. Warner
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COMMITMENT TO GREEN & SUSTAINABLE TRANSFORMATIONS
12 PRINCIPLES OF GREEN CHEMISTRY (Anastas P., Warner J.C., Green Chemistry, Oxford University Press, New York, 1998, p.30)
12 PRINCIPLES OF GREEN CHEMISTRY (Anastas P., Warner J.C., Green Chemistry, Oxford University Press, New York, 1998, p.30)
1. Prevention of waste 2. Atom Economy 3. Less Hazardous Chemical Synthesis
4. Designing Safer Chemicals 5. Safer Solvents and Auxiliaries
6. Design for Energy Efficiency
7. Use of Renewable Feedstocks 8. Reduce Derivatives 9. Catalysis
10. Design for Degradation 11. Real-Time analysis for Pollution Prevention
12. Inherently Safer Chemistry for Accident Prevention
27
28
For you, how many essential pillars are contained in the 12 principles?
• 1
• 2
• 3
• 4
• 5
Audience Survey Question ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT
2/16/2017
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renewable
obtained from an eco-respectful process
demonstrating a favorable
environmental impact
THE 3 PILLARS
OF GREEN CHEMISTRY
29
RENEWABLE RAW MATERIALS
RENEWABLE = if carbon content from renewable source is above 50% of its total carbons.
FIRST PILLAR
>> new ISO Guidelines
on Natural and Organic Cosmetic ingredients and products
To date 52 % (by volume) of all Raw Material Portfolio are from renewable origin
30 30
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52% (2016) by volume of our Raw Materials from renewable origin:
1400 Raw Materials
290 Botanical species
60 Countries
OUR RENEWABLE RAW MATERIALS FIRST PILLAR
31 31
NATURALNESS INDEX
=
ORIGIN INDEX
+
DENATURATION INDEX
FIRST & SECOND PILLARS
32 32
https://www.youtube.com/watch?v=svc9givqhe0 L’Oréal Naturalness Index
2/16/2017
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O.I. = ORIGIN INDEX
Plant (Organics/wild)
Plant Farming Mineral
Fossil
Animal
D.I. = DENATURATION INDEX
5 4 3 2 1 No inf.
5 4 3 2 1 No inf.
CRUDE
EXTRACTION
WITHOUT
PETROCHEMICAL SOLVENT
SLIGHTLY
DENATURING
PROCESS
ORIGIN & NATURALNESS INDEXES
MIXTURE
INTEGRATING
FOSSIL RM
ORIGIN INDEX RENEWABLE ORIGIN ≥ 4
NATURALNESS INDEX : NATURAL ORIGIN ≥ 3.8
STRONGLY
DENATURING
PROCESS
GREEN CHEMISTRY
RAW MATERIAL/NATURAL ORIGIN
N.I.= 3.8
O.I.= 4 or 5
with D.I..= 3
+
= N.I. = NATURALNESS INDEX
NATURALNESS INDEX : NATURAL ≥ 4
FIRST & SECOND PILLAR
33
SOME OF OUR METRICS
TOWARDS GREEN CHEMISTRY PROCESS SECOND PILLAR
ATOM ECONOMY = Molecular mass of the desired product /by the molecular mass
of all reactants (x 100%)
E-FACTOR = amount of waste generated by kg (or ton) of the final ingredient during its
manufacture (R. Sheldon, Green Chem., 2007, 9, 1273-1283)
We need calculation of the E-FACTOR with and without water
if it is possible, in order, notably, to evaluate water consumption
34
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THE NEW FORMULA
REDUCES THE ENVIRONMENTAL FOOTPRINT
+ CO2 + H2O
O2 + +
IMPROVING THE % OF BIODEGRADABILITY
LOWERING THE WATER FOOTPRINT
https://www.youtube.com/watch?v=h6MYI5JFDGo L’Oréal assessment of Water Footprint
THIRD PILLAR
35
GREEN CHEMISTRY PASSPORT
NB OF STEPS WITH EXTREME CONDITIONS
(<-15°C OR > 150°C OR >10H)
E-FACTOR
= RENEWABLE + ECO-RESPECTFUL PROCESS + NO UNFAVORABLE ENVIRONMENTAL IMPACT
THREE PILLARS
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RENEWABLE
INGREDIENTS
DEVELOPMENT
37 37
37
DID YOU KNOW IT?
L'Oréal was the 1st company to launch on the market eco‐designed C‐GLYCOSIDE
38
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39
Collaborations with suppliers on BIOBASED PRODUCTS
RENEWABLE INGREDIENTS DEVELOPMENT
xylose rhamnose mannose
O.I. = 4 D.I. = 3 N.I. = 3.8
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TO IMPROVE & DISCOVER NEW BENEFITS
Ideal building blocks
Sustainable starting materials
Green chemistry compatible
Ecofriendly final products
Non toxic
O
R5
R4
OR
3O
R2
O H
R1
41
No
protecting
group
Eco-friendly
solvents Straightforward
routes
RENEWABLE
STARTING
MATERIALS
ECO-FRIENDLY
PROCESSES
ENVIRONMENTAL
& HUMAN
SAFETY
Is L’OREAL chemistry able to reach 1, 2 …. or all these goals ?
? ? ?
? ?
?
42
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GLYCOSAMINOGLYCAN
Galacto
se
Galactose uronic
acid Xylose
Core protein
PROTEOGLYCAN (PG)
O
OHO
OH
O
NH
O
OXylose
Serine
Key components of the skin extracellular matrix are :
Glycosaminoglycans GAGs, Proteoglycans PGs, Collagens, Elastin
O
OHO
OH
R1
R2
-C-glycoside
?
SUGAR
LINKER
mimic
But before chemistry a little bit of biology……..
43
DETECTION OF A NEW GREEN PROCESS:
Formation of C-glycosides by a tandem Knoevenagel/Michael in H2O
OR
3O
OH
O H
R2
O H
R1
O
C H3
OR
3O
OH
O H
R2
R1
CH3
O O
C H3
N a H C O3
H 2 O
9 0 ° C9 H - 1 2 H
( g l u c o s e , m a n n o s e , c e l l o b i o s e ) - C - g l y c o s i d e
Lubineau A. et al., Chem. Commun. 2000, 2049-2050
Opening on access to β-C-glycosides / One-step synthesis
Reaction in water / Applicable to various saccharides (mono and disaccharides)
Limited scope of activated methylene nucleophiles
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SUGARS: a wide platform for SYNTHETIC CHEMISTRY
CH2
A
OR
OH
OH
OHn
n=0,1
OHOR
OH
OH
OHn
n=0,1
?
Mono-functional C-glycoside
Di-functional C-glycoside
CH
A
OR
OH
OH
OH
A*
n
n=0,1
How to open the chemical space towards
new C-glycosides without using any protecting group?
How to open the chemical space towards
new C-glycosides without using any protecting group?
45
O
OH O H
O H
O
O
OH O H
O H
N
O R
O
OH O H
O H
N H R
O
OH O H
O H
O
R
O H
O
OH O H
O H
O H
1. Reduction
Opening the chemical space of C-glycosides mono-functional C-xylosides
2. Oxime formation 3. Reductive amination
4. Aldol condensation
WO2014096699 WO2010063948 WO2010067036 WO2010063953
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O O H
O H
O HOH
CH3
CH3
O
O
O
O HO HOH
O
C H3 O
O HO HOH
O H
C H3+
H 2 O
9 0 ° C
( D - x y l o s e )
H 2 O
c a t . r e d u c t i o nb a s e
Candidate Selected, Developped & Marketed as a New Antiaging Active
PROXYLANE TM
Sustainable Starting Material Xylose from Beech Wood
Green Process at the 100 t level => efficient synthesis (2 steps), use of water as solvent, use of catalysis
E factor 4,9 Ecofriendly Compound: no bioaccumulation and no ecotoxicity
PROXYLANETM
Synthesis of Pro-Xylane TM: A new biologically active C-glycoside in aqueous media M. Dalko-Csiba and al. Biorg. M
ed Chem. Letters , 2009, 19 (3), pp. 845-849. L’Oreal Patent : WO2002051828
47 47
ProXylane™
6 month clinical study (versus placebo):
Effect on :
- overall skin strength
- tone
- elasticity
- smoothness and homogeneity
In vivo results
ProXylane™ at 10% in cosmetic support
Launched on the market
Eur. J. Dermatol. 2008, 18, 297 Eur. J. Dermatol. 2008, 18, 36
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O
OH O H
O H
O
O
OH O H
O H
N
O R
O
OH O H
O H
N H R
O
OH O H
O H
O
R
O H
O
OH O H
O H
O H
1. Reduction
2. Oxime formation 3. Reductive amination
4. Aldol condensation
Opening the chemical space (mono-functional C-xylosides)
49
O O H
O H
O HOH
CH3
CH3
O
O
N a H C O3
O
O HO HOH
O
C H3
O
O H
OH O HO H
O H
O M e
O
O H
O M e
H+
H 2 O
9 0 ° C
( D - x y l o s e )
2 . c a t . r e d u c t i o n
6 8 % 6 2 - 7 0 %
1 .
6 months clinical trial on going
L’Oreal Patents : WO2010067036 & WO 2014096699
ProXylane R0064930
Atom economy 75% 81%
% Renewable C 60% 81%
Environmental impact not ecotoxic not ecotoxic
NaOH aq 50%
IPrOH/water 30°C
New more potent Candidate Selected
50
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Opening the chemical space (di-functional C-xylosides)
CH2
A
OR
OH
OH
OHn
n=0,1
OHOR
OH
OH
OHn
n=0,1
?
Mono-functional C-glycoside
Di-functional C-glycoside
CH
A
OR
OH
OH
OH
A*
n
n=0,1
How to open the chemical space towards
new C-glycosides without using any protecting group?
How to open the chemical space towards
new C-glycosides without using any protecting group?
51
Inspiration from literature:
another
Knoevenagel/Michael
tandem reaction1
1 On the synthesis of C glycosyl compounds containing double bonds without the use of protecting groups
Carbohydrate Res. 1994, 257, pp 81-95
N
N
O
O
RO
R
O O H
OH O H
O H
O H
O N
N
O
O O
R
R
O HOH
O H
O H
N a+
N a H C O3
w a t e r , h e a t
98% Yield (D-glucose)
one-pot
without protecting group
in water
Discovery and development
of a new synthetic
methodology O N
N
O
O O
C H3
C H3
O HOH
O H
O H
N a+
O
OO HOH
O H
O H O H
NH
C H3
H2
O2
w a t e r
without protecting group
in water
Route to hydroxy amides, esters and acids
52
2/16/2017
27
L’Oréal patent pending
O
OH
OH OH
OH
OH
O
OH
O
OH
OH OH
OH
NH
OH
O
O
OH
OH OH
OH
NH
OH
O
O
OH
OH OH
OH
NH
OH
O
O
OH
OH OH
OH
O
NH
O
OH
OH OH
NH
OH
OO
OOH
OH
OH
O
OH
OH
OHOH
NH
O
OH
new
method
O
O H
OH O H
NH
O H
O
O H
R
Improved synthesis for further chemical diversity
53 53
C-glycosides (mimetics of O-glycosides with higher stability) an overview
OH
OHO
R5
R4O
R3O
R2
R1
O
O
R6
O
R5
R4O
R3O
R2
R1
O
OOHOH
OH
OH
OOHOH
OH
OH
OH
O
O
R5
R4O
R3O
R2
R1
NHR
7
O
R5
R4O
R3O
R2
R1
NOR
8
R6: F, H, Me, Bn
Pro-Xylane
Aldolisation,reduction
Reduction
Reductiveamination
Oximes
Amides
Esters
Lubineau
Alkoxy-amines
Secondary amines
Ketones
Diacids
O
R5
R4O
R3O
R2
OH
R1
Mono, di or trisaccharides
O
R5
R4O
R3O
R2
R1
OH
OH
O
O
R5
R4O
R3O
R2
R1
O
R11
R10
R9
Amides
Esters-Hydroxy-acides
Cyclic ketones
collab. P.Anastas
54
2/16/2017
28
O OH
OH
OH
OH
New types of C-glycosides synthetized : More than 300 → SAR studies New reactions discovered New ingredients identified and developed… and further to be launched in the market
C-glycosides: great knowledge & valuable know-how at L’OREAL
CONCLUSION & PERSPECTIVES
55
SHARING BEAUTY WITH ALL INNOVATING SUSTAINABLY AT L’OREAL
« We have no desire to do Green Chemistry. We desire to do the best Chemistry, and it happens to be green. »
P. T. Anastas Science for a Sustainable Society Symposium, McGill
No
protecting
group
Eco-friendly
solventsStraightforward
routes
RENEWABLE
STARTING
MATERIALS
ECO-FRIENDLY
PROCESSES
ENVIRONMENTAL
& HUMAN
SAFETY almost
56 56
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29
• L’OREAL Research & Innovation teams
(10 years from conception to development and continuous exploration)
• CHIMEX teams
• L. RICARD (X-Ray) at Ecole Polytechnique
• Pr. LUBINEAU’s team at Paris-Sud University
• Pr ANASTAS’s team at Yale University
ACKNOWLEDGEMENTS
57
REFERENCES
https://www.youtube.com/watch?v=h6MYI5JFDGo L’Oréal assessment of Water Footprint
https://www.youtube.com/watch?v=svc9givqhe0 L’Oréal Naturalness Index
http://youtu.be/QOi3ja1TaDo L’Oréal commitment to Green Chemistry
P.T. Anastas and J.C. Warner, Green Chemistry, Theory and practice, Oxford University Press, New-York, 1998, p.30.
http://www.sharingbeautywithall.com/fr (accessed 14/02/17).
M. Philippe, B. Didillon and L. Gilbert, Green Chem., 2012, 14, 952.
M. Philippe, A. Cavezza, P. Pichaud, S. Trouille and M. Dalko-Csiba, Carbohydr. Chem., 2014, 40, 1.
R.A. Sheldon, “The E factor: fifteen years on”, Green Chem., 2007, 9, 1273.
J. Hitce, M. Crutizat, C. Bourdon, A. Vivès, X. Marat and M. Dalko-Csiba, Green Chem., 2015, 17, 3756-3761.
Q. Zhang, M. Benoit, K. de Oliveira Vigier, J. Barrault, G. Jégou, M. Philippe and F. Jérôme, Green Chem., 2013, 15, 963.
M. Philippe, B. Didillon and L. Gilbert, Annales des falsifications, de l’expertise chimique & toxicologique, 2016, 985, 36-43.
Rodrigues, F; Canac, Y; Lubineau, Andre, Chem Comm (2000), (20), 2049-2050 Hersant, Y; Abou-Jneid, R; Canac, Y; Lubineau, A; Philippe, M; Semeria, D; Radisson, X; Scherrmann, M Carbohydr Res (2004), 339(3), 741-745.
58
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30
59
“Natural, Sustainable Innovation: L’Oréal’s Commitment to Renewable Materials and Eco-Friendly Processes”
www.acs.org/acswebinars
Slides available now! Recordings will be available once they are posted.
Michel Philippe L’Oréal Fellow,
L’Oréal
David Constable Science Director,
Green Chemistry Institute,
The American Chemical Society
Xavier Marat Group Leader,
Advanced Research, L’Oréal
This ACS Webinar is being co-produced by the ACS Green Chemistry Institute
gcande.org 60
• Sustainable Chemicals
• Flexible Chemical
Manufacturing
• More Efficient Processes
• Green Chemistry Curricula
• Circular Economy
Considerations
• Sustainable Materials
• Academic-Industry
Collaborations
• Chemicals Policy
• Cosmetics
• And More!
Early Bird Registration will be open from February 15 until April 28, 2017
2/16/2017
31
Upcoming ACS Webinars www.acs.org/acswebinars
61 Contact ACS Webinars® at [email protected]
Thursday, February 23, 2017
Fighting Cancer: Epigenetic Targets for Oncology Session 2 of the 2017 Drug Design and Delivery Symposium
Stuart Conway, Professor of Organic Chemistry, University of Oxford Sharan Bagal, Senior Medicinal Chemist, AstraZeneca
Thursday, March 2, 2017
TERA-print: From Academic Discovery to a Commercial Desktop Fab Session 2 of the 2017 Industrial Science Series
Chad Mirkin, Director, International Institute for Nanotechnology Mark Jones, Executive External Strategy and Communications Fellow, Dow Chemical
62
“Natural, Sustainable Innovation: L’Oréal’s Commitment to Renewable Materials and Eco-Friendly Processes”
www.acs.org/acswebinars
Slides available now! Recordings will be available once they are posted.
Michel Philippe L’Oréal Fellow,
L’Oréal
David Constable Science Director,
Green Chemistry Institute,
The American Chemical Society
Xavier Marat Group Leader,
Advanced Research, L’Oréal
This ACS Webinar is being co-produced by the ACS Green Chemistry Institute
2/16/2017
32
“This ACS Webinar presented just the right mix of actual chemistry and practical applications to make it worthwhile for every participant. I used to work in the field myself and really appreciated the way the presenter organized the material.”
Frans Zonnevijlle, Consultant at Intex Diagnostika AG, ACS member for 40 years strong!
How has ACS Webinars benefited you?
®
Quote in reference to: http://bit.ly/CosmeticChemistry
Be a featured fan on an upcoming webinar! Write to us @ [email protected] 63
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Upcoming ACS Webinars www.acs.org/acswebinars
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Thursday, February 23, 2017
Fighting Cancer: Epigenetic Targets for Oncology Session 2 of the 2017 Drug Design and Delivery Symposium
Stuart Conway, Professor of Organic Chemistry, University of Oxford Sharan Bagal, Senior Medicinal Chemist, AstraZeneca
Thursday, March 2, 2017
TERA-print: From Academic Discovery to a Commercial Desktop Fab Session 2 of the 2017 Industrial Science Series
Chad Mirkin, Director, International Institute for Nanotechnology Mark Jones, Executive External Strategy and Communications Fellow, Dow Chemical