1M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Politecnico di Milano, Department of Chemistry, Materials and Chemical Engineering “G. Natta”
Serinol: a biosourced building block for better mechanical reinforcement and sustainable vulcanization
of rubber compounds
Maurizio Galimberti
Vincenzina Barbera, Giuseppe Infortuna, Valeria Cipolletti1, Attilio Citterio, Shuquan Sun2
Present addresses: 1Pirelli Tyre, 2BUCT Beijing
2M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Research on sustainable chemistry
ISCaMaPInnovative Sustainable Chemistry and Materials and Proteomics
Group
3M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Raw materials, from renewable sources, are easily available
No impact on the food chain
To use wastes and residues
Syntheses according to principles of green and sustainable chemistry
Good economic perspectives
ISCaMaPInnovative Sustainable Chemistry and Materials and Proteomics
Group
Research on sustainable chemistry. Key features
4M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Objective of the research
5M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Sustainable chemistry and rubber technology
Objective of the research
Quiringh Gerritsz. van BrekelenkamA Cobbler at work, his wife spinning wool
6M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Selection of starting building block
Synthesis of derivatives: control of reaction pathways
Innovative chemicals for rubber compounds
Mechanical reinforcement
Vulcanization
Outline of the presentation
7M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Selection of starting building block
Synthesis of derivatives: control of reaction pathways
Innovative chemicals for rubber compounds
Mechanical reinforcement: in brief
Vulcanization: main subject
Outline of the presentation
8M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
2-amino-1,3-propanediol
Selection of the building block: serinol
9M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Selection of the building block: serinol
OH
HO OH
NH2
HO OH
chemical synthesis bacterial synthesis (E. Coli)
glycerol
Sugar caneserinol
10M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Why serinol for rubber compounds?
Starting building block for many reaction pathways: many derivatives
Chemoselectivity
Interaction with polar fillers and polar surroundings
Active role in vulcanization
11M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Starting building block for many reaction pathways: many derivatives
Chemoselectivity
Why serinol for rubber compounds?
12M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Starting building block for many reaction pathways: many derivatives
Chemoselectivity
Why serinol for rubber compounds?
Reactions of the amino group with carbonyl compounds
13M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reactions of the primary amines with carbonyl compounds
Only imines are formed
14M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reactions of the primary amines with carbonyl compounds
Only imines are formed
Imines and Oxazolidines are formed
With amino alcohols
15M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reactions of serinol with carbonyl compounds
O
O
O
O
O
O
O
O
O
Formaldehyde
Cinnamaldehyde
3-methylbenzaldehyde
acetone
5-methylpentanone
Cyclohexanone
Acetophenone
Benzophenone
Fluorenone
Camphor
2,4-pentandione
Carbonyl compounds
Aldehydes Ketones
16M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Neat reactions of serinol with aldehydes
No solvent, no catalyst, T > melting point of carbonyl compound
17M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Neat reactions of serinol with aldehydes
No solvent, no catalyst, T > melting point of carbonyl compound
Carbonyl
compound
Yield (%) Product Type
56 Oxazolidine
92 Imine
98 imineO
18M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Neat reactions of serinol with ketones
No solvent, no catalyst, T > melting point of carbonyl compound
Carbonyl
compound
Yield (%) Product Type
90 Oxazolidine
95 Oxazolidine
90 Oxazolidine
83 Imine
75 Imine
80 Imine
70 Imine
95 Imine
O
NOH
OH
N
HO
HO
19M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Imines from the reaction of serinol with carbonyl compounds
Aromatic and sterically hindered carbonyl compounds
lead to Imines
Carbonyl
Compound
Product Yield (%)
92
98
83
80
70
75
95
N
HO
HO
20M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Oxazolidines from the reaction of serinol with carbonyl compounds
Aliphatic carbonyl compounds with low steric hindrance
lead to oxazolidines
Carbonyl
Compound
Product Yield
(%)
56
90
95
90
21M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
In the presence of acidic catalyst
22M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
In the presence of acidic catalyst
23M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
In the presence of acidic catalyst
24M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
In the presence of acidic catalyst
25M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
HONH2
HO
RO
R'
HONH2
HO
R
O
R'
first molecule VI
26M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
HONH2
HO
RO
R'
HONH2
HO
R
O
R'HO
NHHO
ROH
R'
first molecule VIIVI
27M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
HONH2
HO
RO
R'
HONH2
HO
R
O
R'HO
NHHO
ROH
R' ONH2
O
H
H
first molecule second moleculeVII
HONH
HO
ROH2
R' ONH2
O
H+
VIIIVI
28M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
HONH2
HO
RO
R'
HONH2
HO
R
O
R'HO
NHHO
ROH
R' ONH2
O
H
H
first molecule second moleculeVII
HONH
HO
ROH2
R' ONH2
O
H+
VIIIVI
29M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
HONH2
HO
RO
R'
HONH2
HO
R
O
R'HO
NHHO
ROH
R' ONH2
O
H
H
HONH
HO
RR' O
NH2
O
H
OH
NHO
RR'
ONH2
OH
H
H2O
NHO
HO R'
R
NHHO
O R'R
first molecule second moleculeVII
X
HONH
HO
ROH2
R' ONH2
O
H+
VIII
IXXIXII
VI
30M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
HONH2
HO
RO
R'
HONH2
HO
R
O
R'HO
NHHO
ROH
R' ONH2
O
H
H
HONH
HO
RR' O
NH2
O
H
OH
NHO
RR'
ONH2
OH
H
H2O
NHO
HO R'
R
NHHO
O R'R
first molecule second moleculeVII
X
HONH
HO
ROH2
R' ONH2
O
H+
VIII
IXXIXII
VI
OH
NHO
RR'
ONH2
OH
HX
31M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
HONH2
HO
RO
R'
HONH2
HO
R
O
R'HO
NHHO
ROH
R' ONH2
O
H
H
HONH
HO
RR' O
NH2
O
H
OH
NHO
RR'
ONH2
OH
H
H2O
NHO
HO R'
R
NHHO
O R'R
first molecule second moleculeVII
X
HONH
HO
ROH2
R' ONH2
O
H+
VIII
IXXIXII
VI
OH
NHO
RR'
ONH2
OH
H
NHO
HO R'
R
XXI
32M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
HONH2
HO
RO
R'
HONH2
HO
R
O
R'HO
NHHO
ROH
R' ONH2
O
H
H
HONH
HO
RR' O
NH2
O
H
OH
NHO
RR'
ONH2
OH
H
H2O
NHO
HO R'
R
NHHO
O R'R
first molecule second moleculeVII
X
HONH
HO
ROH2
R' ONH2
O
H+
VIII
IXXIXII
VI
OH
NHO
RR'
ONH2
OH
H
NHO
HO R'
R
NHHO
O R'R
XXIXII
33M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
NHHO
O R'R
XII
Without steric hindrance
and aromatic substituents
With steric hindrance
and aromatic substituents
OH
NHO
RR'
X
34M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
HONH2
HO
RO
R'
HONH2
HO
R
O
R'HO
NHHO
ROH
R' ONH2
O
H
H
H2O
first molecule second moleculeVII
HONH
HO
ROH2
R' ONH2
O
H+
VIIIVI
HONH
HO
RR' O
NH2
O
H
IX
OH
NHO
RR'
ONH2
OH
H
NHO
HO R'
R
NHHO
O R'R
XXIXII
Reaction of serinol with carbonyl compounds. Mechanism
Without acidic catalyst
35M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with carbonyl compounds. Key intermediates
In the presence of acidic catalyst Without acidic catalyst
NH R'
R N CR'
R
36M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Control of synthetic pathways to serinol imines and oxazolidines
37M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Control of synthetic pathways to serinol imines and oxazolidines
38M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Control of synthetic pathways to serinol imines and oxazolidines
39M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Reaction of serinol with dicarbonyl compound
40M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Serinol and serinol derivatives
for rubber compounds
41M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Mechanical properties
Vulcanization
Serinol and serinol derivatives for rubber compounds
42M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Mechanical properties
Serinol and serinol derivatives for rubber compounds
43M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
M. Galimberti, V. Barbera, R. Sebastiano, A. Citterio, G. Leonardi, A.M. Valerio WO 2016 050887 A1
Functionalization of sp2 carbon allotropes
sp2 carbon allotropes+
SP
Functionalized sp2 carbon allotropes
thermal or mechanical energy
M. Galimberti, V. Barbera, S. Guerra, A. Bernardi, Rubber Chemistry and Technology: 2017, 90( 2) 285-307
44M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Paal – Knorr reaction to SP
Carbonallotrope
Carbocatalyzed Oxidation of SP
Diels-Alder reaction
Domino reaction for the functionalization of sp2 carbon allotropes
CBHSAG
CNT
M. Galimberti, V. Barbera, S. Guerra, A. Bernardi, Rubber Chemistry and Technology: 2017, 90( 2) 285-307
45M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Ingredient With CB With CB-SP
CB N326 25 0
CB N326-SP 0 27CB326 0 25SP 0 2
IR 50, BR 50, Silica 50, Silane TESPT 2, Stearic acid 2, ZnO 2.5, 6PPD 2, Sulphur 1.5, TBBS 1.8
CB-SP in CB/Silica based composite
46M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
CB-SP
0
0,02
0,04
0,06
0,08
0,1
0,12
0,14
0,16
0,1 1 10 100
Tan δ
S i %Strain %
CB-SP
CB-SP in CB/Silica based composite
47M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
NH
NH
NH
Serinol camphorimine
DPG
Serinol
N OH
OH
Serinol cinnamaldehydeimine
Serinol acetoneoxazolidine
Serinol and serinol derivatives for rubber compounds
M. Galimberti, R. Sebastiano, V. Barbera, V. Cipolletti, G. Leonardi, S. Sun, L. Rossiello WO 2017/115253 A1
48M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Ingredient phrS-SBR 96.3
NR 15
BR 15
Silica 65
Silane TESPT Si69 5.6
Oil MES 10
Stearic Acid 2
ZnO 2.5
6PPD 2
Sulphur 1.8
TBBS 1.2
Secondaryaccelerator
X
Serinol and serinol derivatives as secondary accelerators in silica based compounds
NH
NH
NH2.4
0.83
2.04
or
or
1.87
Xphr
Secondaryaccelerator
or
Secondary accelerators were used in equal molar amount
49M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Secondary accelerator = DPG
Parameter
ML [dNm] 2.8 2.3
MH [dNm] 13.3 15.1
ts1 [min] 2.8 2.9
t90 [min] 11.5 7.1
0
2
4
6
8
10
12
14
16
0 5 10 15 20
Torque
S' [dN
m]
Time [min]
DPG
Ref
Curing at 170°C
50M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Secondary accelerator = DPG Serinol
Parameter
ML [dNm] 2.8 2.3 3.1
MH [dNm] 13.3 15.1 15.0
ts1 [min] 2.8 2.9 2.6
t90 [min] 11.5 7.1 9.5
0
2
4
6
8
10
12
14
16
0 5 10 15 20
Torque
S' [dN
m]
Time [min]
DPG
Serinol
Ref
Curing at 170°C
51M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Secondary accelerator = DPG Serinol SCam
Parameter
ML [dNm] 2.8 2.3 3.1 2.6
MH [dNm] 13.3 15.1 15.0 14.6
ts1 [min] 2.8 2.9 2.6 3.0
t90 [min] 11.5 7.1 9.5 10.5
0
2
4
6
8
10
12
14
16
0 5 10 15 20
Torque
S' [dN
m]
Time [min]
DPG
Serinol
SCam
Ref
Curing at 170°C
52M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Secondary accelerator = DPG Serinol SCam SOxa
Parameter
ML [dNm] 2.8 2.3 3.1 2.6 2.8
MH [dNm] 13.3 15.1 15.0 14.6 14.8
ts1 [min] 2.8 2.9 2.6 3.0 2.4
t90 [min] 11.5 7.1 9.5 10.5 9.2
0
2
4
6
8
10
12
14
16
0 5 10 15 20
Torque
S' [dN
m]
Time [min]
DPG
Serinol
SOxa
SCam
Ref
Curing at 170°C
53M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Secondary accelerator = DPG Serinol SCam SCin SOxa
Parameter
ML [dNm] 2.8 2.3 3.1 2.6 2.7 2.8
MH [dNm] 13.3 15.1 15.0 14.6 13.6 14.8
ts1 [min] 2.8 2.9 2.6 3.0 2.7 2.4
t90 [min] 11.5 7.1 9.5 10.5 9.2 9.2
Curing at 170°C
54M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
0
0,2
0,4
0,6
0,8
1
1,2
1,4
1,6
1,8
2
0,1 1 10 100
Stor
age
Mod
ulus
G' [
MPa
]
Strain [%]
DPG
Serinol
SCam
SCin
SOxa
Strain sweep at 170°C
55M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
aScorch time ts5: = time needed to have an increase of torque of 5 dNm
Secondary accelerator = DPG Serinol SCam SOxa SCin
Parameter
ML dNm 7.1 6.1 7.0 6.5 6.6 6.1
ts5a min 46.4 28.9 25.7 37.3 20.6 27.0
Scorch time at 130°C
56M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
2 h Boiling hexane
NH
NH
NH
Silica based masterbatch (1 : 1) with
2 h Boiling hexane
2 h Boiling hexane
Solvent extraction of silica / secondary accelerator masterbatches
57M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
2 h Boiling hexane
NH
NH
NH
Silica based masterbatch (1 : 1) with
2 h Boiling hexane
2 h Boiling hexane
Solvent extraction of silica / secondary accelerator masterbatches
NONE
Extracted substance
58M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
r.t.,14 days
+
SiO2 150 , 2 h
No weight loss
weight loss
Camphor(80% extracted)
Thermal treatment of silica / SCam masterbatch
1 : 1
59M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Ingredient Composite
phr phr phr
NR 100 100 100
Stearic acid 2 2 2
ZnO 5 5 5
Sulphur 2 2 2
CBS 1.5 1.5 1.5
Serinol - 0.83 ‐
Scam - - 2.04
Serinol and serinol derivatives as secondary accelerators in NR based compounds
60M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Secondary accelerator = Serinol SCam
Parameter
ML [dNm] 1.1 1.6 1.3MH [dNm] 8.5 8.7 8.7ts1 [min] 2.1 2.6 2.3
t90 [min] 4.6 2.0 2.6
Curing at 170°C
0123456789
10
0 2 4 6 8 10 12Time [min]
Torq
ue S
’ [dN
m]
Serinol
SCam
Ref.
61M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
ts2 vs curing Temperature
0
1
2
3
4
5
6
7
8
145 150 155 160 165 170 175 180 185
Ref.
SCam
Serinol
t s2[m
in]
Temperature [°C]
(T°C): 151 160 170 180
62M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
t90 vs curing Temperature
0
2
4
6
8
10
12
140 150 160 170 180 190
Ref.
SCam
Serinol
Temperature [°C]
t 90[m
in]
(T°C): 151 160 170 180
63M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Vulcanization rate vs Temperature
0
5
10
15
20
25
145 150 155 160 165 170 175 180 185
Serinol
SCam
Ref.
∆(M
H-M
L)/(T
90-T
S2)
[d
Nm
/min
]
Temperature [°C]
(T°C): 151 160 170 180
64M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Kinetics of vulcanization
Vulcanization temperatures (°C): 151, 160, 170, 180
Induction and crosslinking
0123456789
10
0 2 4 6 8 10 12Time [min]
Torq
ue S
’ [dN
m]
Experimental data elaborated through Arrhenius equation
65M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Ea (kJ/mol)
Serinol
Ref.
SCam
121.2
57.7
84.7
Kinetics of vulcanization
Induction
66M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Ea (kJ/mol)
91.1
99.7
84.7
Serinol
Ref.
SCam
Kinetics of vulcanization
Crosslinking
67M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Conclusions
68M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Conclusions
69M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Conclusions
70M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Conclusions
NHHO
O R'R OH
NHO
RR'
71M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Conclusions
0
2
4
6
8
10
12
14
16
0 5 10 15 20
Torque
S' [dN
m]
Time [min]
DPG
Serinol
SCam
Ref
NHHO
O R'R OH
NHO
RR'
0123456789
10
0 2 4 6 8 10 12Time [min]
Torq
ue S
’ [dN
m]
72M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
Acknowledgments
BUCT (Beijing) for supporting Shuquan Sun PhD period at Politecnico
Pirelli Tyre
Enhancing science, technology and business across the evolving elastomeric community.
73M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
74M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017
ISCaMaPInnovative Sustainable Chemistry and Materials and Proteomics
Group
2
75M. Galimberti et al Serinol: a biosourced building block International Elastomer Conference Cleveland (OH), October 9-12, 2017