“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

TRFA Annual Meeting- Montreal, Canada 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

TRFA Annual Meeting- Montreal, Canada Introduction High Purity resin Low melt viscosity High heat resistance Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Chemical structure and characteristics 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 Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada High performance resins Difunctional DCPD type epoxy resin Multifunctional DCPD type epoxy resin Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

High performance resins Difunctional 1,5-Dihydroxy Naphthalene type epoxy resin Tetra functional Naphthalene type epoxy resin Difunctional Dihydroxy Biphenyl type epoxy resin Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Epoxy resins used for present study Diglycidyl ether of Bisphenol-A (DGEBA)- YD 128 Epoxy Phenol Novolac (EPN)- YDPN 638 Epoxy Tetramethyl Bisphenol-S (ETMBPS) Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Preparation of ETMBPS Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Properties of various epoxy resin used for present study 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 Melting point (oC) - 114 Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada GPC of ETMBPS DSC of ETMBPS Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Physical form of various epoxy resin used for present study Epoxy Phenol Novolac (EPN) Diglycidyl ether of Bisphenol-A (DGEBA) Epoxy Tetramethyl Bisphenol-S (ETMBPS) Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Melt viscosity Vs. Temperature of various epoxy resins Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

Curing agents used for present study Phenol Novolac (PN) HRJ 1583 Tris(4-hydroxyphenyl) methane (THPM) 3,3’-Diaminodiphenyl Sulphone (3,3’-DDS) Omicure 3,3’-DDS Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Properties of curing agent used for present study Properties PN THPM DDS Hydroxyl equivalent weight (g/eq) (Functionality) 106 (3.6) 97 (3) - Amine equivalent weight (g/eq) 62 (4) Softening point (oC) 78 102 Melting point (oC) 177 Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Mixing ratio used for laminate preparation Resin Hardener Catalyst Ratio (Part by weight) YD 128 3,3-DDS Anchor 1040 100 33.0 1 YDPN 638 35.0 ETMBPS 28.6 HRJ 1583 TPP 56.4 0.5 60.5 49.0 THPM 51.6 55.4 45.0 Binder- Fiber ratio : 30: 70 Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada % Weight loss Vs. Temperature by TGA Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada 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

TRFA Annual Meeting- Montreal, Canada YD 128/ HRJ 1583/ TPP YDPN 638/ HRJ 1583/ TPP ETMBPS/ HRJ 1583/ TPP Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada YD 128/ THPM/ TPP YDPN 638/ THPM / TPP ETMBPS/ THPM / TPP Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Electrical properties of various systems Property Test Method Unit 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 IEC60093 Ohms-cm 1016 Surface resistance Ohm 1013 Dielectric constant IEC60250 - 3.50 4.30 3.23 3.85 3.79 3.71 3.28 2.51 Dielectric loss % 1.5 1.9 1.6 1.0 Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada

TRFA Annual Meeting- Montreal, Canada 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

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

TRFA Annual Meeting- Montreal, Canada Thank You Sept,11, 2006 TRFA Annual Meeting- Montreal, Canada