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• Sustainable Chemicals • Sustainable Materials

• Flexible Chemical • Academic-Industry
Manufacturing Collaborations
• More Efficient Processes • Chemicals Policy
• Green Chemistry Curricula • Cosmetics
• Circular Economy • And More!
Considerations
Early Bird Registration will be open from February 15 until April 28, 2017
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 2/16/2017

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.

11

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 2/16/2017

Upcoming ACS Webinars

www.acs.org/acswebinars

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

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Contact ACS Webinars® at acswebinars@acs.org 13

“Natural, Sustainable Innovation: L’Oréal’s Commitment

to Renewable Materials and Eco-Friendly Processes”

David Constable Xavier Marat Michel Philippe

Group Leader, L’Oréal Fellow,
Science Director,
Advanced Research, L’Oréal L’Oréal
Green Chemistry Institute,
The American Chemical Society

Slides available now! Recordings will be available once they are posted.
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7
 2/16/2017

NATURAL, SUSTAINABLE INNOVATION:

L’ORÉAL’S COMMITMENT TO RENEWABLE
MATERIALS & ECO-FRIENDLY PROCESSES
Michel PHILIPPE, PhD and Xavier MARAT, PhD - L’Oréal R&I

1st WORLDWIDE COSMETIC GROUP

205 Products sold every second

25.8 Billions € (2016)

140 countries

82,900 people

32 International
brands

16

8
 2/16/2017

ALL THE BEAUTY NEEDS

Make up Hair care Perfume Skincare Hair dye

17

Audience Survey Question

ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT

About how many patents does L'Oreal hold?

• Almost 250 patents
• Almost 300 patents
• Almost 425 patents
• Almost 500 patents
• Almost 750 patents

18

9
 2/16/2017

RESEARCH & INNOVATION

761
748
680
624
582
523 539

2008 2009 2010 2011 2012 2013 2014

3,870 497
794M € (2015) people patents

19

20

10
 2/16/2017

I N N OVAT I N G DEVELOPPING
SUSTAINABLY SUSTAINABLY

PRODUCING LIVING
SUSTAINABLY SUSTAINABLY

21

INNOVATING
SUSTAINABLY

BY 2020, WE WILL INNOVATE

SO THAT 100% OF OUR
PRODUCTS HAVE AN
ENVIRONMENTAL
OR SOCIAL BENEFIT.

22

11
 2/16/2017

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

12
 2/16/2017

L'Oréal has implemented

Green Chemistry Principles for Many Years

25
http://youtu.be/QOi3ja1TaDo L’Oréal commitment to Green Chemistry

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

26

13
 2/16/2017

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)

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

Audience Survey Question

ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT

For you, how many essential pillars are contained in the 12

principles?
• 1
• 2
• 3
• 4
• 5
28

14
 2/16/2017

THE 3 PILLARS
OF GREEN CHEMISTRY

renewable

obtained from an
eco-respectful process

demonstrating
a favorable
environmental impact

29

RENEWABLE RAW MATERIALS

FIRST PILLAR
RENEWABLE = if carbon content from
renewable source is above 50% of its total
carbons.

>> 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

15
 2/16/2017

OUR RENEWABLE RAW MATERIALS

FIRST PILLAR
52% (2016) by volume of our Raw Materials from renewable origin:

1400 Raw Materials

290 Botanical species

60 Countries

31
31

FIRST & SECOND PILLARS

NATURALNESS INDEX
=
ORIGIN INDEX
+
DENATURATION INDEX

https://www.youtube.com/watch?v=svc9givqhe0
32
L’Oréal Naturalness Index 32

16
 2/16/2017

ORIGIN & NATURALNESS INDEXES

FIRST & SECOND PILLAR
Plant
Plant
(Organics/wild)
Farming Mineral Fossil Animal

5 4 3 2 1 No inf.
O.I. = ORIGIN INDEX

+ 5 4 3 2 1 No inf.

D.I. = DENATURATION INDEX

= CRUDE
MIXTURE
INTEGRATING
N.I. = NATURALNESS INDEX FOSSIL RM
EXTRACTION SLIGHTLY STRONGLY
WITHOUT DENATURING DENATURING
PETROCHEMICAL SOLVENT PROCESS PROCESS
ORIGIN INDEX RENEWABLE ORIGIN ≥ 4
GREEN CHEMISTRY
NATURALNESS INDEX : NATURAL ORIGIN ≥ 3.8 RAW MATERIAL/NATURAL ORIGIN
NATURALNESS INDEX : NATURAL ≥ 4 N.I.= 3.8
O.I.= 4 or 5
with D.I..= 3
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

17
 2/16/2017

THE NEW FORMULA

REDUCES THE ENVIRONMENTAL FOOTPRINT
THIRD PILLAR

IMPROVING THE % OF LOWERING THE WATER

BIODEGRADABILITY FOOTPRINT

+ + O2

+ CO2 + H2O

https://www.youtube.com/watch?v=h6MYI5JFDGo L’Oréal assessment of Water Footprint

35

GREEN CHEMISTRY PASSPORT

THREE PILLARS
= RENEWABLE + ECO-RESPECTFUL PROCESS + NO UNFAVORABLE ENVIRONMENTAL IMPACT
E-FACTOR

NB OF STEPS
WITH EXTREME CONDITIONS
(<-15°C OR > 150°C OR >10H)

36

18
 2/16/2017

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

19
 2/16/2017

39

RENEWABLE INGREDIENTS DEVELOPMENT

Collaborations with suppliers on BIOBASED PRODUCTS

O.I. = 4
D.I. = 3
N.I. = 3.8
xylose rhamnose mannose

40

20
 2/16/2017

R5 Ideal building blocks

R1
O  Sustainable starting materials
R4O
R3O OH  Green chemistry compatible
R2  Ecofriendly final products
 Non toxic

TO IMPROVE & DISCOVER

NEW BENEFITS
41

Is L’OREAL chemistry able to reach 1, 2 …. or all these goals ?

? ? ?

No
Straightforward protecting Eco-friendly
routes group solvents

RENEWABLE ENVIRONMENTAL
ECO-FRIENDLY
? STARTING & HUMAN ?
PROCESSES
MATERIALS SAFETY

42

21
 2/16/2017

But before chemistry a little bit of biology……..

Key components of the skin extracellular matrix are :

Glycosaminoglycans GAGs, Proteoglycans PGs, Collagens, Elastin

PROTEOGLYCAN (PG)

GLYCOSAMINOGLYCAN SUGAR
LINKER Core protein

uronic
acid Galactose Galacto Xylose
se

HO
O O
O
HN
O
?
O O
HO
Xylose H
O R2
O
Serine mimic H
O
-
C
-
g
l
yc
o
s
i
dR
1
e43

DETECTION OF A NEW GREEN PROCESS:

Formation of C-glycosides by a tandem Knoevenagel/Michael in H2O

O O

H 3 C C H 3

O H N a H C O O H
3
O O
R 3 O H 2O R 3 O R
R 1 1 C H 3

O H 9 0 °C R
H O R H O 2
2 9 H - 1 2 H O

( g lu c o s e , m a n n o s e , c e llo b io s e )  - C - g ly c o s id e

 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

Lubineau A. et al., Chem. Commun. 2000, 2049-2050 44

22
 2/16/2017

SUGARS: a wide platform for SYNTHETIC CHEMISTRY

Mono-functional C-glycoside

A
R O CH2

R O OH
? HO n OH
OH
n=0,1
HO n OH
OH
n=0,1 Di-functional C-glycoside

A
ROC
How to open the chemical space towards HA
*

new C-glycosides without using any protecting group? H

O O
nH
O
H
n
=0
,
1
45

Opening the chemical space of C-glycosides

mono-functional C-xylosides

1. Reduction O 4. Aldol condensation R

O O

OH O O OH
HO OH H O O H HO OH
OH O H OH

2. Oxime formation 3. Reductive amination

OR
O N
O NHR

HO OH
HO OH
OH
WO2014096699 OH
WO2010063948
WO2010067036
WO2010063953

46

23
 2/16/2017

Candidate Selected, Developped & Marketed as a New Antiaging Active

H 3 C
PROXYLANE TM
O O H O
b a s e O C H 3 O C H
+ c a t. r e d u c tio n 3

H O O H O H 2O O O H
H 2O
O H H 3 C 9 0 °C H O O H H O O H
O H O H
(D -x y lo s e )

PROXYLANETM

 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

Synthesis of Pro-Xylane : A new biologically active C-glycoside in aqueous media M. Dalko-Csiba and al. Biorg. M
TM

ed Chem. Letters , 2009, 19 (3), pp. 845-849. L’Oreal Patent : WO2002051828

47
47

ProXylane™ In vivo results

6 month clinical study (versus placebo):

Effect on :
- overall skin strength
- tone
- elasticity
- smoothness and homogeneity

Launched on the market

Eur. J. Dermatol. 2008, 18, 297 ProXylane™ at 10% in cosmetic support

Eur. J. Dermatol. 2008, 18, 36

48

24
 2/16/2017

Opening the chemical space (mono-functional C-xylosides)

1. Reduction O 4. Aldol condensation R

O O

OH O O OH
HO OH H O O H HO OH
OH O H OH

2. Oxime formation 3. Reductive amination

OR
O N
O NHR

HO OH
HO OH
OH
OH

49

New more potent Candidate Selected

O H

O
H3C O M e O H
O O H N a H C O
O 3
H
H 2O O C H NaOH aq 50% O
+ 3 1. IPrOH/water 30°C O M e
H O O H O
9 0 °C O 2 . c a t. r e d u c tio n O H
H3C H O O H
O H 68% H O O H 6 2 -7 0 %
O H O H
(D -x y lo s e )

ProXylane R0064930

Atom economy 75% 81%

% Renewable C 60% 81%

6 months clinical trial on going

Environmental impact not ecotoxic not ecotoxic

L’Oreal Patents : WO2010067036 & WO 2014096699

50

25
 2/16/2017

Opening the chemical space (di-functional C-xylosides)

Mono-functional C-glycoside

A
R O CH2

R O OH
? HO n OH
OH
n=0,1
HO n OH
OH
n=0,1 Di-functional C-glycoside

A
ROC
How to open the chemical space towards HA
*

new C-glycosides without using any protecting group? H

O O
nH
O
H
n
=0
,
1
51

Route to hydroxy amides, esters and acids

Inspiration from literature: O

N
R
+
R
Na
another OH
O
OH
O N O
N
Knoevenagel/Michael O OH O R O N
R
tandem reaction1 NaHCO3
O
HO OH w a te r, h e a t HO OH
one-pot in water OH OH

(D-glucose) 98% Yield

without protecting group

Discovery and development +

CH3
Na
of a new synthetic OH
O N O
OH OH
methodology O N
H2O2
O
H
N
CH3 CH3
w a te r
in water O O
HO OH HO OH

without protecting group OH OH

1 Onthe synthesis of C glycosyl compounds containing double bonds without the use of protecting groups 52
Carbohydrate Res. 1994, 257, pp 81-95

26
 2/16/2017

Improved synthesis for further chemical diversity

OH OH
H
O N
R
O
HO OH
OH
new
method

OH OH OH OH HO
H H OH OH
O OH O N O N H
HO O N
O
O O O O
HO OH HO OH HO OH HO O OH
OH OH OH OH OH

OH OH OH OH OH OH
H H H
O N O N O N

O O O
HO OH HO OH HO OH
OH OH OH

L’Oréal patent pending

53
53

C-glycosides (mimetics of O-glycosides with higher stability) an overview

R1 R5 O
O HO
O HO HO
R4 O HO OH
R3 O HO
HO
R2 HO
Pro-Xylane HO O
HN
Secondary am ines R7

Reduction Aldolisation, R1 R5 O Am ides

R1 R5 reduction R6
Reductive R4 O O
R4 O O R3 O OH
am ination
R3 O R1 R5
R2
Alkoxy- R2 O O OH
am ines R4 O
R3 O R 6 : F, H, M e, Bn
N Esters
O xim es O R8 R2 Diacids
Ketones O

Lubineau

R1 R5
R4O O
R3O OH
R2
Mono, di or trisaccharides
R1 R5 Amides
R R10
R5 11 R4O OOH
R1
R9 R3O
collab. P. R4O O
OH
R3O R2
Anastas Esters
R2 -Hydroxy-acides O
Cyclic ketones O

54

27
 2/16/2017

CONCLUSION & PERSPECTIVES

C-glycosides: great knowledge & valuable know-how at L’OREAL

O OH

OH
HO
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
55

SHARING BEAUTY WITH ALL

INNOVATING SUSTAINABLY AT L’OREAL
RENEWABLE
« We have no desire to do Green STARTING
Chemistry. We desire to do the MATERIALS
best Chemistry, and it happens to
be green. »
P. T. Anastas ECO-FRIENDLY
Science for a Sustainable Society Symposium, McGill PROCESSES

No
Straightforward protecting Eco-friendly ENVIRONMENTAL
solvents
routes group & HUMAN
SAFETY
almost

56
56

28
 2/16/2017

ACKNOWLEDGEMENTS
• 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

57

REFERENCES
http://youtu.be/QOi3ja1TaDo L’Oréal commitment to Green Chemistry
https://www.youtube.com/watch?v=svc9givqhe0 L’Oréal Naturalness Index
https://www.youtube.com/watch?v=h6MYI5JFDGo L’Oréal assessment of Water Footprint
http://www.sharingbeautywithall.com/fr (accessed 14/02/17).
P.T. Anastas and J.C. Warner, Green Chemistry, Theory and practice, Oxford University Press, New-York, 1998,
p.30.
R.A. Sheldon, “The E factor: fifteen years on”, Green Chem., 2007, 9, 1273.

M. Philippe, B. Didillon and L. Gilbert, Green Chem., 2012, 14, 952.

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.

Q. Zhang, M. Benoit, K. de Oliveira Vigier, J. Barrault, G. Jégou, M. Philippe and F. Jérôme, Green Chem., 2013, 15, 963.
M. Philippe, A. Cavezza, P. Pichaud, S. Trouille and M. Dalko-Csiba, Carbohydr. Chem., 2014, 40, 1.
J. Hitce, M. Crutizat, C. Bourdon, A. Vivès, X. Marat and M. Dalko-Csiba, Green Chem., 2015, 17, 3756-3761.
M. Philippe, B. Didillon and L. Gilbert, Annales des falsifications, de l’expertise chimique & toxicologique, 2016, 985, 36-
43. 58

29
 2/16/2017

“Natural, Sustainable Innovation: L’Oréal’s Commitment

to Renewable Materials and Eco-Friendly Processes”

David Constable Xavier Marat Michel Philippe

Group Leader, L’Oréal Fellow,
Science Director,
Advanced Research, L’Oréal L’Oréal
Green Chemistry Institute,
The American Chemical Society

Slides available now! Recordings will be available once they are posted.
www.acs.org/acswebinars
This ACS Webinar is being co-produced by the ACS Green Chemistry Institute 59

• Sustainable Chemicals • Sustainable Materials

• Flexible Chemical • Academic-Industry
Manufacturing Collaborations
• More Efficient Processes • Chemicals Policy
• Green Chemistry Curricula • Cosmetics
• Circular Economy • And More!
Considerations
Early Bird Registration will be open from February 15 until April 28, 2017
gcande.org 60

30
 2/16/2017

Upcoming ACS Webinars

www.acs.org/acswebinars

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

Contact ACS Webinars® at acswebinars@acs.org 61

“Natural, Sustainable Innovation: L’Oréal’s Commitment

to Renewable Materials and Eco-Friendly Processes”

David Constable Xavier Marat Michel Philippe

Group Leader, L’Oréal Fellow,
Science Director,
Advanced Research, L’Oréal L’Oréal
Green Chemistry Institute,
The American Chemical Society

Slides available now! Recordings will be available once they are posted.
www.acs.org/acswebinars
This ACS Webinar is being co-produced by the ACS Green Chemistry Institute 62

31
 2/16/2017

How has ACS Webinars®

benefited you?
Quote in reference to: http://bit.ly/CosmeticChemistry

“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!

Be a featured fan on an upcoming webinar! Write to us @ acswebinars@acs.org 63

64

32
 2/16/2017

Benefits of ACS Membership

Chemical & Engineering News (C&EN)
The preeminent weekly news source.

NEW! Free Access to ACS Presentations on Demand®

ACS Member only access to over 1,000 presentation recordings from
recent ACS meetings and select events.

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Your source for leadership development, professional education,
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http://bit.ly/benefitsACS 65

ACS Webinars® does not endorse any products or services. The

views expressed in this presentation are those of the presenter and
do not necessarily reflect the views or policies of the American
Chemical Society.

Contact ACS Webinars® at acswebinars@acs.org 66

33
 2/16/2017

Upcoming ACS Webinars

www.acs.org/acswebinars

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

Contact ACS Webinars® at acswebinars@acs.org 67

34