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“Synthesis and study of a crystalline epoxy resin for high heat resistance” Pradip K. Dubey*, Hitesh. K. Soni, Mahesh Soni, Samir Kanitkar Thitikan, Patcharaporn Aditya Birla Chemicals (Thailand) Ltd- Epoxy Division. Introduction. Emerging needs Miniaturization of electronic components - PowerPoint PPT Presentation
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Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 1
“Synthesis and study of a crystalline epoxy resin for high heat resistance”
Pradip K. Dubey*, Hitesh. K. Soni, Mahesh Soni, Samir Kanitkar Thitikan, Patcharaporn
Aditya Birla Chemicals (Thailand) Ltd- Epoxy Division
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 2
Introduction
Emerging needs
Miniaturization of electronic components
High speed data transfer
Lower dielectric constant and high heat resistance
Possible to apply in lower thickness
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 3
Introduction
High Purity resin
Low melt viscosity
High heat resistance
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 4
Hydrophobic/ saturated backbone – lower dielectric constant
Higher aromatic content - higher heat resistance
Purity/ symmetry- crystalline / lower melt viscosity
High functionality/ high crosslink density – high heat resistance
Chemical structure and characteristics
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 5
CH2CH
O
H2C CH2 CH CH2
O
O O
O O OCH2 CH CH2
O
CH2 CH CH2
O
CH2 CH CH2
O
n
High performance resins
Multifunctional DCPD type epoxy resin
Difunctional DCPD type epoxy resin
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 6
High performance resins
O
O
CH2 CH CH2
O
CH2CH
O
H2C
CH2CH
O
H2C
CH2 CH CH2
O
O
CH2
O
OO
CH2 CH CH2
O
CH2CH
O
H2C
Difunctional 1,5-Dihydroxy Naphthalene type epoxy resin
O CH2 CHOCH2CH
O
H2C CH2
O
Difunctional Dihydroxy Biphenyl type epoxy resin
Tetra functional Naphthalene type epoxy resin
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 7
C
CH3
CH3
O CH2 CHOCH2CH
O
H2C CH2
O
O H2C
OH2C
O
2.6
CH2
CH
CH2O
CH2
CH
CH2O
CH2
CH
CH2O
S
O
O
O CH2 CH
O
CH2OCH2CH
O
H2C
H3C
H3C
CH3
CH3
Diglycidyl ether of Bisphenol-A (DGEBA)- YD 128
Epoxy Phenol Novolac (EPN)- YDPN 638
Epoxy Tetramethyl Bisphenol-S (ETMBPS)
Epoxy resins used for present study
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 8
OHH3C CH3
H2SO4
S
O
O
H3C
HO
H3C
CH3
OH
CH3
Scheme I
2,6-Dimethyl phenol Bis(3,5-dimethyl-4-hydroxyphenyl) sulphone
2 H2O
H2C
O
CHCH2ClS
O
O
H3C
HO
H3C
CH3
OH
CH3
S
O
O
H3C
O
H3C
CH3
O
CH3
H2C
O
CHCH2 H2CHC
O
CH2
Scheme II
Bis(3,5-dimethyl-4-hydroxyphenyl) sulphone
Epichlorohydrin
+2 +
+ NaCl+ H2O+NaOH
Diglycidyl ether of bis(3,5-dimethyl-4-hydroxyphenyl)sulphone
Preparation of ETMBPS
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 9
Properties YD 128 YDPN 638 ETMBPS
Epoxy equivalent weight (g/eq) 188.0 175.1 216.7
Hydrolysable chlorine (% w/w) 0.0574 0.072 0.0034
Total chlorine (% w/w) 0.17 0.18 0.062
Viscosity (oC), cPs 12200 @25oC
29094 @ 52oC
119.1 @ 120oC
Number average molecular weight (g/mol)(Functionality)
380(2)
600(3.6)
421(2)
Melting point (oC) - - 114
Properties of various epoxy resin used for present study
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 10
GPC of ETMBPS DSC of ETMBPS
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 11
Physical form of various epoxy resin used for present study
Diglycidyl ether of Bisphenol-A (DGEBA) Epoxy Phenol Novolac (EPN)
Epoxy Tetramethyl Bisphenol-S (ETMBPS)
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 12
Melt Viscosity
0
200
400
600
800
1000
1200
1400
1600
1800
120 130 140 150 160 170 180
Temperature, oC
Vis
co
sit
y,
cP
s
ETMBPS ECN EPN
Melt viscosity Vs. Temperature of various epoxy resins
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 13
OH H2C
OHH2C
OH
2.6
C
H
OHHO
OH
S
H2N NH2O
O
3,3’-Diaminodiphenyl Sulphone (3,3’-DDS) Omicure 3,3’-DDS
Phenol Novolac (PN)
HRJ 1583 Tris(4-hydroxyphenyl) methane (THPM)
Curing agents used for present study
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 14
Properties PN THPM DDS
Hydroxyl equivalent weight (g/eq)(Functionality)
106(3.6)
97(3)
-
Amine equivalent weight (g/eq)(Functionality)
- - 62(4)
Softening point (oC) 78 102 -
Melting point (oC) - - 177
Properties of curing agent used for present study
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 15
Resin Hardener Catalyst
Ratio (Part by weight)
Resin Hardener Catalyst
YD 128 3,3-DDS Anchor 1040 100 33.0 1
YDPN 638 3,3-DDS Anchor 1040 100 35.0 1
ETMBPS 3,3-DDS Anchor 1040 100 28.6 1
YD 128 HRJ 1583 TPP 100 56.4 0.5
YDPN 638 HRJ 1583 TPP 100 60.5 0.5
ETMBPS HRJ 1583 TPP 100 49.0 0.5
YD 128 THPM TPP 100 51.6 0.5
YDPN 638 THPM TPP 100 55.4 0.5
ETMBPS THPM TPP 100 45.0 0.5
Mixing ratio used for laminate preparation
Binder- Fiber ratio : 30: 70
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 16
Glass transition temperature of different systems
100
120
140
160
180
200
DGEBA EPN ETMBPS
Epoxy resin system
Gla
ss t
ran
siti
on
te
np
erat
ure
, o
C
PN
3,3'-DDS
THPM
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 17
% Weight loss Vs. Temperature by TGATGA- 5% degradation
300
320
340
360
380
400
420
PN DDS THPM
Curing agent system
Tem
per
atu
re,
0C
DGEBA
EPN
ETMBPS
TGA- 10% degradation
320
340
360
380
400
420
440
PN DDS THPM
Curing agent system
Tem
per
atu
re,
oC
DGEBA
EPN
ETMBPS
TGA-20% degradation
320
340
360
380
400
420
440
PN DDS THPM
Curing agent system
Tem
per
atu
re,
oC
DGEBA
EPN
ETMBPS
TGA-50% degradation
0
100
200
300
400
500
600
PN DDS THPM
Curing agent system
Tem
pera
ture
, o
CDGEBA
EPN
ETMBPS
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 18
Tensile strength Vs. Curing agents
050
100150200250300350400
PN DDS THPM
Curing agents
Ten
sil
e s
tren
gth
, M
Pa
DGEBA
EPN
ETMBPS
Tensile Modulus Vs. Curing agents
0
5000
10000
15000
20000
25000
30000
PN DDS THPM
Curing agents
Ten
sil
e M
od
ulu
s,
MP
a
DGEBPA
EPN
ETMBPS
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 19
Flexural strength Vs. Curing agents
0
100
200
300
400
500
PN DDS THPM
Curing agent system
Fle
xu
ral
str
en
gth
, M
Pa
DGEBA
EPN
ETMBPS
Flexural Modulus Vs. Curing agents
0
5000
10000
15000
20000
25000
PN DDS THPM
Curing agent system
Fle
xu
ral
Mo
du
lus,
MP
a
DGEBA
EPN
ETMBPS
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 20
Impact strength of various epoxy systems
020406080
100120140160180200
PN DDS THPM
Cring agents
Imp
act
stre
ng
th,
KJ/
sq.m
t
DGEBA
EPN
ETMBPS
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 21
Stress distribution during fracture by Impact
YD 128/ DDS/ Anchor 1040
YDPN 638/ DDS/ Anchor 1040
ETMBPS/ DDS/ Anchor 1040
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 22
YD 128/ HRJ 1583/ TPP
YDPN 638/ HRJ 1583/ TPP
ETMBPS/ HRJ 1583/ TPP
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 23
YD 128/ THPM/ TPP
YDPN 638/ THPM / TPP
ETMBPS/ THPM / TPP
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 24
PropertyTest
MethodUnit
YD128/ DDS/
Anchor 1040
YDPN 638/ DDS/
Anchor 1040
ETMBPS / DDS/ Anchor
1040
YD128/ HRJ1583/
TPP
YDPN638/ HRJ1583/
TPP
ETMBPS / HRJ1583/
TPP
YD128/
THPM / TPP
YDPN638/ THPM /
TPP
ETMBPS / THPM /
TPP
Volume resistivity
IEC60093Ohms-cm
1016 1016 1016 1016 1016 1016 1016 1016 1016
Surface resistance
IEC60093 Ohm 1013 1013 1013 1013 1013 1013 1013 1013 1013
Dielectric constant
IEC60250 - 3.50 4.30 3.23 3.85 3.79 3.50 3.71 3.28 2.51
Dielectric loss
IEC60250 % 1.5 1.9 1.9 1.5 1.9 1.9 1.5 1.6 1.0
Electrical properties of various systems
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 25
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 26
Conclusion:
High purity ETMBPS exhibits lower melt viscosity in uncured form.
ETMBPS shows higher Tg compared to conventional epoxy resin system.
ETMBPS cured systems shows better dielectric constant and dielectric loss compared to other systems.
Mechanical properties of ETMBPS systems are comparable or lower compared to other systems.
Properties at elevated temperature need to be studied further to establish true potential of this resin
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 27
Potential application areas
• Laminates involving high temperature and electrical properties
• Electronic molding compounds
• Powder coating of electrical and electronic components
• One component adhesives
Sept,11, 2006
TRFA Annual Meeting- Montreal, Canada 28
Thank You