acce 2002, september 13- bio based thermoset resins and their composites€¦ · ·...
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ACCE 2002, September 13ACCE 2002, September 13--14, 200214, 2002
BioBio--based based Thermoset Thermoset Resins and Resins and Their CompositesTheir Composites
M. M. MisraMisra, L. T. Drzal, A. K. , L. T. Drzal, A. K. MohantyMohanty, L. , L. BelchlerBelchler, , G. G. MehtaMehta, J, J--P. P. Latere DwanLatere Dwan’’sIsasIsa
Michigan State UniversityMichigan State University2100 Engineering Building, East Lansing, MI, 488242100 Engineering Building, East Lansing, MI, 48824
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Presentation OutPresentation Out--linelineIntroduction and motivationIntroduction and motivation
BioBio--based resins, Biobased resins, Bio--fibers and Biofibers and Bio--CompositesComposites
BiobasedBiobased Epoxies and Their CompositesEpoxies and Their CompositesBiobased PolyurethanesBiobased Polyurethanes and Their Compositesand Their CompositesBiobasedBiobased Unsaturated Polyesters and Their Unsaturated Polyesters and Their CompositesComposites
ConclusionsConclusions
AcknowledgementsAcknowledgements
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Motivation
BLENDof Functionalized Oil
WITH Thermoset Resins?(Thermoset Resins:
Brittle & Expensive)
ECONOMY:Economically Viable
HOW ? Example: Epoxy ResinCosts 126 cents/lb.
WhereasEpoxidized Oils
Costs ~ 60 Cents/lb
TECHNOLOGY:To ImproveToughness
ECOLOGICALBENEFIT:
Incorporation OfBio-resources
To the MaximumPermissible Extent
To achieve Required Properties
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NATURAL FIBERSNATURAL FIBERS
FLAXFLAX HEMPHEMP
COIRCOIR
WOODWOOD
JUTEJUTE HENEQUENHENEQUEN
KENAFKENAF
Woven JUTE Cloth
GRASSGRASSCORNCORN
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Natural/BioNatural/Bio--Fiber Composites (BioFiber Composites (Bio--Composites)Composites)
Thermoplastic basedThermoplastic based Thermoset Thermoset based based
BiofiberBiofiber-- ThermoplasticThermoplastic( Polypropylene/PVC/PS)( Polypropylene/PVC/PS)
Green: PLA, Cellulose esters etc.Green: PLA, Cellulose esters etc.
BiofiberBiofiber--ThermosetsThermosets(Epoxy, Polyesters, (Epoxy, Polyesters, PolyurethanesPolyurethanes))
BioBio--based: Blend with based: Blend with functionalizedfunctionalizedVegetable oilVegetable oil
HYBRID BIOHYBRID BIO--COMPOSITESCOMPOSITES(Fiber blending/Matrix blending)(Fiber blending/Matrix blending)
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Thermoset vs. thermoplastic composites
• Use of reinforced thermoset composites: ~doubled in the last decade
• Expected to increase 47% during next 5 years through 2004
• ~ 65% of all composites use glass fiber - polyester composites.
• Natural fiber polyester composites: target is to replace glass-polyester composites
70%Reinforcedunsaturated polyester
15%otherthermosets
15%Reinforcedthermoplastics
Matrix patternin Polymer Composites
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BioBio--based Epoxies based Epoxies and and
their Compositestheir Composites
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ReagentsDGEBA (Diglycidylether of bisphenol A)
m = 0, 1, 2
O
CH OCH2
CH3
CH3
C O CCH2 CH CH2 O O CH2 CH CH2
O
CH3
CH3OH
m
J-T403 (Jeffamine T403) MPDA (m-phenylene diamine)
NH2
NH2
CH2CH CH3 NH2
CH2
CH2
CH3CH2 C CH2 O
CH2CH CH3 NH2O
CH2CH CH3 NH2O
X
Y
Z
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Reagents: Epoxidized Soy(ESO)/Linseed Oils(ELO)
CH2 C CH2 7 CH CH CH2 CH CH CH2 4 CH3
CH2 O C CH2 4 CH CH CH2 CH CH CH2 CH CH CH2 4 CH3
CH2 O C 7 CH CH CH2 7 CH3CH2
O
OO
O OO
O O O
O
Epoxy equivalent wt. of ESO: 225-230
CH2 C CH2 7 CH CH CH2 CH CH CH2
CH2 O C CH2 4 CH CH CH2 CH CH CH2 CH CH CH3
CH2 O C 7 CH CH CH2 7 CH3CH2
O
OO
O OO
O O O
O
CH2 CH3
CH2
CH CH
O
Epoxy equivalent wt. of ELO: 173-178
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Epoxy-Primary Amine Curing Reaction
O
CH OCH2
CH3
CH3
C O CCH2 CH CH2 O O CH2 CH CH2
O
CH3
CH3OH
m
C C
O
+ RNH2 HO C C NHR
+C C
O
HO C C NHR HO C N C C OH
R
C
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* taken from Tensile Measurements
0
0.5
1
1.5
2
2.5
3
3.5
ESO(10) ESO(20) *ESO(30) ELO(10) ELO(20) ELO(30)Samples
Mod
ulus
(GPa
)Dynamic Mechanical Analysis of Bio-based Epoxy Resin with Jeffamine T403 at 30°C
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Impact Strength and Glass Transition Temp. of Bio-based Epoxy Resin with T 403
0
100
200
300
400
ESO(10%) ESO(20%) ESO(30%) ELO(10%) ELO(20%) ELO(30%)Samples
Impa
ct S
tr. (J
/m)
0
20
40
60
80
Tg (°C
)
IS Tg
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Modulus of Elasticity & Bending Strength of Epoxy Samples containing ELO and MPDA
0
1
2
3
4
0% ELO 30% ELO 40% ELO 50% ELO
Samples
Mod
ulus
of
Elas
tici
ty (G
Pa)
0
50
100
150
Bend
ing
Stre
ngth
(MPa
)MOEBending Str.
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Impact Strength of Epoxy Samplescontaining MPDA and ELO
0
20
40
60
80
100
120
0% ELO 30% ELO 40% ELO 50% ELO Samples
Impa
ct S
tren
gth
(J/m
)
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ESEMs of Impact Fractured Epoxy Resin containing MPDA and ELO
Scale: 5µm 10 µm 10 µm
30%ELO X 6000 50% ELO X 500040%ELO X 6000
Phase separation between epoxy-rich phase and ELO-rich phase
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0
20
40
60
80
100
120
0 100 200 300 400 500 600Temperature (°C)
Wei
ght
%
0
0.2
0.4
0.6
0.8
1
1.2
1.4
1.6
1.8
2
Der
ivat
ive
Wei
ght
(%/°
C)
Water-Washed (WW)5%Alkali2%Silane (Z-6040)***Plasma*UV**Water-Washed (WW)5%Alkali2%Silane (Z-6040)***Plasma*UV**
*550 W with O2 for 10 min.
**120 sec. of UV at 60 °C
***Epoxy compatible silane
Thermogravimetric Analysis of Surface Modified Henequen (HQ)
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0
0.5
1
1.5
2
2.5
3
3.5
4
4.5
No ELO or HQ ELO 30V%WW HQ
30V%5%Alkali HQ
30V%Plasma* HQ
30V%2%SilaneHQ
30V%UV** HQ
Samples
MOE
(GPa
)
0
20
40
60
80
100
120
140
160
Bend
ing
Str
engt
h (M
Pa)
MOE Bending Str.
Modulus of Elasticity (MOE) & Bending Strength of -Epoxy Composites containing 30% ELO and 30V% HQ
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Conclusion
The impact strength was directly proportional to the concentration of the epoxidized oils when using J-T403.The modulus, bending strength, and Tgwere inversely proportional to the concentration of the epoxidized oils when using J-T403.The impact strength was directly proportional to the concentration of the ELO when using 30 or 40% ELO and MPDA.
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BioBio--based based Polyurethanes Polyurethanes & their Composites& their Composites
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Polyurethanes: Synthesis and Uses
HO OH + OCN NCO HO OH+
OCNH
ONCOH
OOCN
O
HNCOH
O
POLYOL DIISOCYANATE
POLYURETHANE
• Fast reaction, no by-product• Wide range of polyols and isocyanates ⇒ numerous uses
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Distinguishing Characteristics of Polyols
250 to 1,00028 to 160Hydroxyl number
3.0 to 8.02.0 to 3.0Functionality
150 – 1,0001,000 to 6,500Molecular weight
Rigid coatings, Rigid foams
Elastomers, Coatings, Flexible foams
Characteristics
(SZYCHER’S HANDBOOK OF PURs), CRC Press (1999).
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HOOH
OH
HO
O
O
O
OOH
HO
HO
OH
HO
POH
OHO
O
O
OHO
OH
O
O
O
O
OO
OH
HO
HO OH
OH
OP
HO OH
O
HO
HO
OH
HO
Soy phosphate ester polyol
Mw = 2304 g/molFunctionality = 20
492 mg KOH/g
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2025181200142714312100
G’ (30˚C) (MPa)
1.064520 / 10061.0697125 / 7551.08811150 / 5041.05114275 / 2530.85515490 / 1021.072167100 / 01
Density (g/cm3)
Tg (˚C) (DMA)
Polyol OH ratio(JEFFOL / SOPEP)
Entry
Properties of Biobased Polyurethane's
Isocyanate / OH ratio = 1.1. Jeffol 495 polyol: polyether polyol(495 mg KOH /g) and SOPEP (154 mg KOH /g). Isocyanate: polymeric diphenylmethane diisocyanate (MDI).
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“Polyol” Hybridization ⇒ Biobased PURs with acceptable properties (thermal, mechanical
performances) and effective cost
Effect of the (Jeffol / SOPEP) OH molar ratio on flexural properties
0
20
40
60
80
100
0/100 25/75 50/50 75/25 90/10 100/0
Flex
ural
ste
ngth
(MPa
)
0
500
1000
1500
2000
Mod
ulus
(MPa
)
Flexural Strength (MPa) Modulus (MPa)
0
10
20
30
40
50
60
70
80
0/100 25/75 50/50 75/25 90/10 100/0
OH molar ratio (Jeffol/SOPEP)
Impa
ct s
treng
th (J
/m)
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Glass reinforced Polyurethanes from soy phosphate ester polyol: DMA Study
Effect of glass fiber on G' of soy phosphate ester PU
0
500
1000
1500
2000
2500
3000
-10 10 30 50 70 90 110 130 150
Temperature (C)
G' (
MPa
)
No fiber 15 wt % 30 wt % 50 wt %
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0
20
40
60
80
100
120
No fiber 15 wt % 30 wt % 50 wt %
Flex
ural
stre
ngth
(MPa
)
0
1000
2000
3000
Flex
ural
mod
ulus
(MP
a)
Flexural strength (MPa) Modulus (MPa)0
100
200
300
400
500
600
No fiber 15 wt % 30 wt % 50 wt %Im
pact
stre
ngth
(J/m
) Partial break
Modulus of Elasticity (MOE),Bending Strength and Impact Strength of Glass reinforced
Polyurethanes
⇒ Improvement of mechanical properties (dynamic, flexural and impact)
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10 wt %
50 wt %30 wt %
No fiber
100X
Impact Fractured surfaces of Glass reinforced Polyurethanes
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Conclusions
Preparation of PURs from soy phosphate ester combined with petroleum-based polyol (tuning of properties).
Commercially available plant-based polyols: low OH content for preparation of RIGID polyurethanes ⇒ Glass reinforced PURs from SOPEP.
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Unsaturated Polyester Resins and their Composites
ExteriorExterior (Natural Fiber(Natural Fiber--Polyester): Polyester): UnderUnder-- floor panels, engine & floor panels, engine & transmission covers
Ref.: DaimlerChrysler High Tech Report 1999
transmission covers
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Classification
Unsaturated Polyester Resins
Orthoresins Isoresins
Bisphenol-Afumarates Vinyl ester
resinsChlorendics
General purpose polyester resins (Cheapest resin)
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Nonwoven Hemp –Unsaturated Polyester Composites
0
10
20
30
40
50
60
70
A B C0
5
10
15
20
Tensile Strength (MPa) Tensile Modulus (GPa)
9.29
16.88
25.83
0
5
10
15
20
25
30
A B CIm
pact
Str
engt
h(J/
m)
A: Neat polyester, B: Raw Hemp (30 vol.%)-polyester, C: Surface treated Hemp-polyester
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CONCLUSIONSCONCLUSIONSThermoset Thermoset resins can be effectively blended with resins can be effectively blended with functionalized functionalized
vegetable oil (Stiffnessvegetable oil (Stiffness--toughness balance)toughness balance)Different BioDifferent Bio--based based polyurethanes polyurethanes can be designed and can be designed and
engineered engineered -- -- ReinformentReinforment with biowith bio--fiber/glass fiber result fiber/glass fiber result superior superior physicophysico--mechanical properties.mechanical properties.
BioBio--Composites can Replace/Substitute Glass Fiber CompositesComposites can Replace/Substitute Glass Fiber Composites–– Energy benefitEnergy benefit–– RenewabilityRenewability, biodegradability, CO, biodegradability, CO22 sequestrationsequestration–– Independent of dwindling petroIndependent of dwindling petro--sourcessources–– ValueValue--Added Opportunity for Agriculture IndustryAdded Opportunity for Agriculture Industry
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AcknowledgementsAcknowledgements
NSF-PATH (2001 Award No. 0122108)
Project GREEEN (GR01 Project GREEEN (GR01 –– 037)037)
Bayer AG, Huntsman, Johnson & Manville Bayer AG, Huntsman, Johnson & Manville
ATOFINA Chemicals ATOFINA Chemicals
Flaxcraft & HemplineFlaxcraft & Hempline
KemliteKemlite
Composite Materials & Structures Center Composite Materials & Structures Center -- MSUMSU