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Preparation of Polymer/Silica ParticleNanocomposites and Their Applications

(/)

Nov. 5, 2009

KiRyong Ha ()

2012-05-01


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Colorado

Colorado


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University of Colorado

Three campuses: Boulder, Colorado Springs and Denver.


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National Parks in Colorado

Mesa VerdeNational Park

Rocky MountainNational Park


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National Parks in Colorado

Great Sand Dunes NationalPark

Black Canyon of theGunnison National Park


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Tourist Attractions

Aspen mountainscomprises of 4993acres, forty liftsand 335 trailsalong with sharp

vertical slopes inthe entire Colorado,which makes itmore thrilling and

stimulating.Aspen Colorado Ski Resort
http://2.bp.blogspot.com/_NO2UOMMYKZ0/STPmX9iN6oI/AAAAAAAAC-Y/Rf0g9ltdbbM/s1600-h/Buttermilk+Ski+Map.jpg


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Tourist Attractions

Maroon Bells One Colorado Fall day
http://images.google.co.kr/imgres?imgurl=http://clarkvision.com/galleries/images.colorado.sanjuans/web/colorado.fall.c09.30.2003.L4.9421.c-700.jpg&imgrefurl=http://www.clarkvision.com/galleries/gallery.large_format/web/colorado.fall.c09.30.2003.L4.9421.c-700.html&usg=__LVdHwOfJQE3KwAaLuWdphILaHZQ=&h=555&w=700&sz=334&hl=ko&start=22&sig2=LTpVUGVnhFhgi7_411cccQ&um=1&tbnid=JOCbEw0OkYMifM:&tbnh=111&tbnw=140&prev=/images%3Fq%3DFall%2Bin%2BColorado%26ndsp%3D20%26complete%3D1%26hl%3Dko%26lr%3D%26sa%3DN%26start%3D20%26um%3D1%26newwindow%3D1&ei=oBztSr-BHpD0sgOiw-H1Aw


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Tourist Attractions

Garden of the godsUnited StatesAir Force Academy


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University of Colorado at Boulder


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Our department has been ranked 19th overall and 10th

among public graduate programs by U.S. News & WorldReport, and ranked 4th in average citations per publicationby University Science Indicators.

Department of Chemical and Biological Engineering

Dr. Christopher N. Bowman

Associate Dean for Research,Patten Professor of Chemicaland Biological Engineering,Clinical Professor ofRestorative Dentistry and

Co-Director of the NSF I/UCRCfor Fundamentals andApplications and Photopolyme-rizations


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Outlines

1. Introduction

- Composites and Nanocomposites- Silica & Silane Coupling Agent2. Experimental- Silanization of Silica Particles- Characterization

(a) FTIR(b) TGA(c) Solid State NMR

- Fabrication of Nanocomposites

(a) Curing Kinetics using Real Time NIR(b) DMA results

3. Conclusions


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Introduction


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Composite

20,

000

120,

000

Composite theory is based the rule-of-mixtures (simple version ormodified rule). In almost all cases, the solid dispersed phase is onewith the better properties.

Definition: Materials containing at least two constituents that can be

physically or visibly distinguished. Any two-phase material can beconsidered a composite.


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Composite


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Effect of Fillers

Functional fillers transfer applied stress from the polymermatrix to the strong and stiff mineral.


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Polymer Nanocomposites


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Polymer Matrices


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Dimensions of Nanoparticles


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Preparation of Nanocomposites


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Why Nanocomposites? Multi-functionality

Small filler size:

High surface to volume ratio Small distance between fillers bulk interfacial material

Mechanical Properties

Increased ductility with no decrease of strength,

Scratching resistance

Optical properties Light transmission characteristics particle size dependent

Interaction Zone

Particle


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Production of Precipitated Silica

1) Precipitated silica: reaction of an alkaline silicate solution

with a mineral acid

Na2(SiO2)3.3(aq) + H2SO4(aq) 3.3 SiO2(s) + Na2SO4(aq)


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Production process of fumed silica

2) Fumed silica

Flame pyrolysis of silicon tetrachloride


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Fumed Silica


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TEM of SiIica (OX-50 & AS380)

Formation of aggregates due to high temperature

manufacturing process.

Evonik technical bulletin No. 11

TEM of Aerosil OX-50 TEM of Aerosil 380


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Fumed Silica for Insulating Materials

Thermal Conductivity vs Total Pressure & Pore Size

Reliable and most cost-effective way to reduce both energy use

and CO2 emissions.


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Hydrophobic Treatment of Fumed Silica

Silica is hydrophilic in due to silanol (Si-OH) groups on the surface.These silanol groups may be chemically reacted with various reagentsto render the silica hydrophobic


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Properties of Hydrophobic Fumed Silica


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Production of Monodisperse Nanoparticles

3) Stber-Process

HydrolysisSi(OC2H5)4+ 4H2O Si(OH)4+4C2H5OHCondensationSi(OH)4SiO2+ 2H2O both in a NH3alcohol solution

-monodisperse, spherical silicananoparticles that range in sizefrom 52000 nm.


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Particle-Matrix Compatibility

Regardless of filler size and shape, intimate contact between the matrixand mineral particles is essential, since air gaps represent points ofpermeability and zero strength.


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SiIane Coupling Agent

General Formula:

R: Amino, vinyl, epoxy, chloro, mercapto, methacryloxy,acryloxy, etc.)

X: Hydrolyzable group typically alkoxy, acyloxy, halogen oramine.

Gelest Catalog 3000-A, Silicon compounds: Silanes & Silicones, p. 166, Gelest Inc.


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SiIane Coupling Agent

Silane coupling agents have the ability to form a

durable bond between organic and inorganic materials.Enhance interfacial adhesion via chemical bonding.

Gelest Catalog 3000-A, Silicon compounds: Silanes & Silicones, p. 166, Gelest Inc.


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Silane Coupling agent Treatment

Modification with organosilane depends on the ability to form a bondwith silanol groups, -Si-OH, and/or aluminol groups (-Al-OH) on the fillersurface.


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Typical Silane Coupling Agents

Generally the reactivitydifferences betweenmethoxy and ethoxysilanes are not a problem.At typical hydrolysis pH(acidic ~5, basic ~ 9),both versions hydrolyzein under 15 minutes at

2% silane concentrations.


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Applying a Silane Coupling Agent


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Silane Effectiveness on Inorganics

Hydroxyl-containing substrates

vary widely in concentration andtype of hydroxyl groups present.


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Silane Coupling agent Treatment

SEM photomicrographs of fractured silica-filled epoxy compositea) silica without silane treatment, b) silica with silane treatment.


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CO2 Reduction


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Established Nanotechnologies


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Green Tires

Lower rolling resistance Fuel economy lower carbon dioxide emissions lower global warming impact


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Green Tires


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Green Tires

How can the Silane coupling agent meet the needs?

Si-69; Bis-[-3-(triethoxysilyl)-propyl]-tetrasulfide


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Green Tires

SilicaSilane: How it Works


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Green Tires

SilicaSilane: How it Works


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Green Tires How it works


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Silanes to Meet the Need


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New Silanes for Silica Tire 1


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Green Tires


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Experimental


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Properties of SiIica (OX-50 & Aerosil 380)

1) Noncrystalline form of silicon dioxide (SiO2) Fumed silica

- OX-50: Low specific surface and only slight tendency toagglomerate. ( 2.2 Si-OH/nm2)- Aerosil 380: Highest specific surface area (2.5 Si-OH/nm2)- Hydrophilic grades.2) BET Surface Area [m2/g]: 50 (+-) 15, 380 (+-) 30

3) Average primary particle size: 40 nm, 7 nm4) Tapped density: 130 g/L, 50g/L5 Density: 2.2g/cm3

6)Hardness: 5.36.5 (Mohs Scale)Fillers for transparentscratch-resistant coating

7) Refractive index: 1.46Very close to the most organic monomers8) Tensile strength: 48.3 MPa9) Bulk modulus: ~37 Gpa10) Youngs modulus: 71.7 GPa Fillers for reinforcing

E i t l
http://en.wikipedia.org/wiki/Mohs_scale_of_mineral_hardnesshttp://en.wikipedia.org/wiki/Mohs_scale_of_mineral_hardness


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Experimental

Three parameters which will be dealt here:

1)Filler surface modification

2) Filler concentration

3) Particle size and the particle dispersion state.

E. Chabert, M. Bornert, E. Bourgeat-Lami, J.-Y. Cavaille, R. Dendievel, C. Gauthier,J. L. Putaux, and A. Zaoui, Materials Science and Engineering A 381, 302-330 (2004)

E i t l


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Experimental

1) Silica OX-50 & Aerosil 3802) -methacryloxypropyltrichlorosilane (MPTS)3) [(Biscycloheptenyl)ethyl]tricholorosilane (BCTC)

Materials:

4) TMPTMP (Trimethylolpropane tris(3-mercaptopropionate)

-3 functional S-H-n20 = 1.518, d=1.21 g/ml-b.p. = 220 at 0.3mm Hg, m.w. = 398.565) TMPDE (Trimethylolpropane diallyl ether)

-2 functional allyl ether groups-nD =1.458, d= 0.955 g/ml-b.p. = 135/13mmHg, m.w. = 214.30

Experimental


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Experimental

6) GDMP (Glycol Dimercaptopropionate)

Chemical Formula: (HSCH2CH2COOCH2)2CAS #: 22504-50-3- 2 functional S-H

b.p.: 175-195C, m.w.: 238.32n

25= 1.5-1.51, d = 1.219

7) DMPA (2,2-dimethoxy-2-phenyl-acetophenone)C6H5COC(OCH3)2C6H5, photoinitiator, m.p. = 67~70)

Silane treatment proced re (D St k t )


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1) Silica particles were dried by heating under vacuum2) Dean-Stark trap was used to remove waterin the toluene solvent.

3) Dried silica particles were added to the reaction flaskwith dried toluene.4) Silane solution and triethylamine (catalyst) wereadded and stirred under nitrogen for 18 hrs.

5) The particles were washed with several kinds of solvents anddried in the vacuum oven.

Silane treatment procedure (Dean-Stark trap)

To make monolayer of silane coupling agent on the silica, water

must be removed from the reaction system.

S f G f SiO P i l


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Surface Groups of SiO2 Particles

Evonik technical bulletin No. 11

or isolated

Drying of OX 50


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Drying of OX-50 (FTIR Spectrum of of Pressed Disks)

Pressed OX-50 without any treatment

By drying process, increase of the intensity at 3747cm-1, which is causedby isolated Si-OH was observed (150 for 1hr).

After 1hr heating at150

Before heating

MPTS OX 50 FTIR S t


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MPTS OX-50 FTIR Spectrum

Pressed MPTS OX-50 Pressed Disk

C=C-H stretchingpeak of

methacrylate

AliphaticC-H

C=O

stretching

C=C

Disappearanceof isolated Si-OH

FTIR Results (C O P k Ch )


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(a)

(b)

(c)

FTIR Results (C=O Peak Change)

(a): Pure MPTS liquid, (b): Anhydrous toluene was used toprepare (multilayer), (c) Reflux method was used to prepare.

Q. Liu et al., JOURNAL OF BIOMEDICAL MATERIALS RESEARCH 57(3), 384-393 (2001).

Free C=O

H-bonded C=O C=C

Degradation Pattern by TGA


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Degradation Pattern by TGA

TGA can be used to determine silane content (MPTS on OX-50

& AS380)

M.W. of degrading part: 7 C + 2 O + 11 H= 7 x 12 + 2 x 16 + 11 x 1 = 127 (Assuming all Si-OHgroups reacted; T3 formation)Bond energy of the Si-O-Si bond (444 kJ/mol)Bond energy of the Si-C bond (306 kJ/mol)Bond energy of the C-C bond (345 kJ/mol).

Maher Abboud, Michelle Turner, Etienne Duguet and Michel

Fontanilleb, J. Mater. Chem., 1997, 7(8), 15271532.

TGA Results


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TGA Results

TGA thermogram of MPTS OX-50 & Aerosil 380

TGA results: m (100 800)1.65 wt % loss for OX-50 and 11.8 wt % loss for Aerosil 380Surface area: 7.6 times, wt loss = 7.2 times

TGA Results


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TGA Results

TGA thermogram of BCTC silane coupling agent

TGA results: m (100 800)Reflux method: (1.587% & 1.577% = avg. 1.58% ) weightloss Two step degradation characteristics

Solid State NMR Results (13C & 29Si)


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Solid State NMR Results (13C & 29Si)

29Si = DSX Bruker 400Mhz

Delay time: 3 secContact time: 2 msecSpinning rate: 6kHz

13

C = Bruker Avance II+Spinning rate: 9KHzDelay time: 3 secContact time: 2.5 msec

Cross-polarization combined with magic angle

spinning (CP/MAS) were used to get NMR spectra.4 mm ZrO2 rotorCalibration: TMS

Solid State 29Si NMR


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From 29Si CP/MAS NMR, it is possible to differentiate the different types of

silicon atoms present in the silica particles:Q4, Q3, and Q2, that is, in the bulk, on the surface bonded to one OH and totwo OH, respectively.T1, T2, and T3 correspond to the silicon atoms contained in the silane moleculewhich have formed one (or two, or three, respectively) Si-O-Si bond with thesilica particle, or one Si-O-Si binding between two silanes.

2

29Si NMR Spectrum of Pristine OX-50 & AS380


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Si NMR Spectrum of Pristine OX-50 & AS380

Pristine OX-50

PPM

-200-150-100-500

Sig

na

l

-400

-200

0

200

400

600

800

1000

29

Si NMR can detect three types of silicon atoms at about -90, -100, and -110 ppm, designated Q2, Q3, and Q4 according to the number of OSi groupsbound, as shown below, where R is H or alkyl.Q2 = (RO)2Si(OSi)2,Q

3 = ROSi(OSi)3,Q4 = Si(OSi)4

R. Joseph, S. Zhang, and W. T. Ford, Macromolecules, 29, 1305-1312 (1996).

-99.76(Q3)

29Si NMR Spectrum of AS380

PPM

-200-150-100-500

Signal

-200

0

200

400

600

800

1000

1200

-100.1(Q3)

-91.3(Q2)

29Si NMR Spectrum of MPTS OX 50 & MPTS AS380


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29Si NMR Spectrum of MPTS OX-50 & MPTS AS380

Silane Treated OX-50 (Reflux method)

PPM

-200-150-100-500

Signa

l

-500

0

500

1000

1500

2000

2500

3000

Silanol signals of pristine OX-50 (Q2 & Q3) decrease upon silanization

compared to Q4 signal for MPTS treated OX-50 sample.MPTS AS380 has lower T3 and higher T1 contents compared to MPTS OX-50.

29Si NMR Spectrum of MPTS AS380

PPM

-200-150-100-500

Signal

-200

0

200

400

600

800

-99.9(Q3)

-48.5(T1)

-56.5(T2)

-108.5(Q4)-101.2(Q3)

-67.2(T3)-57.0(T2)

13C NMR Spectrum of MPTS OX-50(3 days vacuum dried sample)


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C NMR Spectrum of MPTS OX 50(3 days vacuum dried sample)

.R. Joseph, S. Zhang, and W. T. Ford, Macromolecules, 29, 1305-1312 (1996).

MPTS modified OX-50

PPM

050100150200

Intensity

-200

0

200

400

600

800

1000

1200

C=C

*

13C NMR Spectrum of MPTS AS380 (after 3 days more


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C NMR Spectrum of MPTS AS380 (after 3 days morevacuum dried sample)

R. Joseph, S. Zhang, and W. T. Ford, Macromolecules, 29, 1305-1312 (1996).

MPTS modified Aerosil 380

PPM

050100150200

Intensi

ty

-2000

0

2000

4000

6000

8000

58.4

*

One more peak at 58.4

ppm observed:1)Rotation about the COC bond may be highlyrestricted due to hydrogenbonding of C=O groups ofmethacryl with Si-OH

groups on the silicasurface, therefore peaksplittings due toconformational differencesmay be observed.2)Residual ethanol

Ethanol: 18.4 and 58.3 ppm

**

* : 22.0 & 16.5 ppm

29Si NMR Spectrum of BCTC OX-50


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Four peaks at-107.9, -103.2, -66.5, -58.0 ppm

29Si Solid State NMR(bicycloheptenylethyltrichlorosilane treated OX-50)

PPM

-200-150-100-500

Intensity

0

200

400

600

800

1000

1200

1400

Si NMR Spectrum of BCTC OX-50

Q4

Q3T2

T3

13C NMR Spectrum of BCTC OX-50 ( ft 3 d


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C NMR Spectrum of BCTC OX-50 (after 3 daysvacuum dried)

BCTC modified OX-50

PPM

050100150200

Intensity

-200

0

200

400

600

800

1000

1200

1400

1600

1800

C=C

Peaks at 136.2, 131.6,

58.1, 48.8, 44.7, 41.9,32.0, 29.0(shoulder), 27.2,16.9, and 10.0 ppm 11peaksBut BCTC has 9 carbons

in the molecule.Therefore, 2 more peaksmay be caused by endo-and exo- form of BCTC.Peaks at 136.2 and 131.6

ppm are by olefinic C=C.

Ethanol: 18.4 and 58.3 ppm

Dispersion test in H2O


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Dispersion test in H2O

2 ml water only in the vial.

OX-50 silica dispersed wellin the water.Some MPTS OX-50dispersed, but most of them

in the bottom of the vial.Most BCTC OX-50 stayed inthe bottom of the vial.

HydrophiliciltyOX-50 > MPTS OX-0 >BCTC OX-50

a) MPTS OX-50 in waterb) BCTC OX-50 in waterc) OX-50 in water

RTIR measurement by NIR


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RTIR measurement by NIR

BeforeUV

After UVDecreaseof thispeak areawas used.

5.0 mW/cm2 intensity

320~500 nm wavelength[{10 mol % TMPTMP+ 90 mol %GDMP} + TMPDE] +0.2 wt % DMPAphotoinitiator

1st overtone of TMPDE C=C-H band

C=CHcombinationband

S-Hband

J. B. Ang, D. JT. Hill, P. J. Pomery, and H. Toh, Polym. Int., 52, 1689-1693 (2003).

Real Time FTIR


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Real Time FTIR

Monitoring reactions in real-time.

Peak area change with UV irradiation was generated in realtime, that is, the data from both UV curing and FTIRmonitoring are collected simultaneously to follow the timedependent decrease of the C=C bond.

Peak area change with UV irradiation time


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Peak area change with UV irradiation time

Time (min)

0 1 2 3 4 5

PeakA

rea

-1

0

1

2

3

4

5

6

UV

irradiationstartedhere

Fabrication of Nanocomposite


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Fabrication of Nanocomposite

Thiol monomer +DMPA solution

Ene MonomerSilica particle

Mixing Mixing + UVComposite

DMA Measurement Conditions


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DMA Measurement Conditions

1. 1 1/2 days storage in the dark at ambient conditions for UV

irradiated samples2. Strain % = 0.8 %, frequency: 3Hz3. Room temperature -80 equilibrate for 2 mins heating

3/ min rate to 180

4. Measurement of three specimens to get average value

DMA Curves for (TMPDE+GDMP) system


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R. B. Bogoslovov, C. M. Roland, A. R. Ellis, A. M. Randall, and C. G. Robertson, Macromolecules,2008, 41, 1289-1296.2012-05-01

DMA Curves for (TMPDE+GDMP) system

1. Modulus in the glassy(-70) and rubbery region (100)increased byaddition of fillers whether thefillers were modified or not. Good reinforcingeffects.

2. The intensity of the tan peak

in all the filler added polymerswas reduced compared topristine (TMPDE+GDMP)system through reduction of thepolymer concentration.

3. Tg was very little affected bythe incorporation of fillers.

4. Shoulder peak can not beremoved after heating, coolingand reheating cycle.

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-0.5

0.0

0.5

1.0

1.5

2.0

2.5

TanDelta

0.1

1

10

100

1000

10000

StorageModulus(MPa)

-80 -30 20 70 120 170

Temperature (C)

DMA10%ox-aDMA10%mpts-a DMApri-b DMA10%bctc-a

Universal V4.3A TA Instruments

Black curve: Pristine

Shoulder?

Effects on Tg


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Effects on Tg

(-25.4 ~ -27.5 : small effecton Tg meansweakinteractionsbetween resinmolecules andfiller surface)

Glassy Region Storage Modulus


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Glassy Region Storage Modulus

Storage Modulus at -70C

Filler Contents (wt %)

0 5 10 15 20

StorageModul

us(GPa)

1.2

1.4

1.6

1.8

2.0

2.2

2.4

2.6

2.8

3.0

OX-50

MPTS OX-50

BCTC OX-50

AS380

MPTS AS380

Generallyincrease withfiller contents.

Rubbery Region Storage Modulus


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y g g

- Strong surface area

effect. (AS380 and MPTSAS380 vs. OX-50 and AS380).- Resin system with OX-50showed lowest storage

modulus at 20 wt% fillerconcentration, whichmay be caused by thepoor dispersion stabilityof OX-50, causingagglomeration.

Particle Size Effect on Transparency


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Particle Size Effect on Transparency

AS380 (primary particle size: 7 nm) incorporated nanocomposites

are more transparent than those of OX-50 (primary particle size:40nm) incorporated nanocomposites.

(a) 15% OX-50 (b) 15% AS 380

FE-SEM Results for TMPTMP+TATATO


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To investigate the dispersion state of the silica nano-partilces inthe cured resin, cured composites were fractured in liquidnitrogen, and then the morphology of the fractured surface wereobserved with FE-SEM.

Results for (TMPDE+GDMP) System


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( ) y

1. The moduli of the TMPDE+GDMP system with silica

particles increased.

2. Nanocomposite with smaller particle sizes such asAS380 & MPTS AS380 as fillers showed higher modulusthan those of OX-50 & MPTS OX-50 incorporatednanocomposites.


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Thank you for your kind attention.

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