New building blocks to expand your formulation options.

JEFFAMINE amine JEFFLINK diamine New building blocks to expand your formulation options. Geert Dries Technical manager urethane chemistries Huntsman Performance Products

Content What is Polyurea? Why develop new molecules? JEFFAMINE amine and JEFFLINK diamine overview Some ideas Summary

What is Polyurea? POLYUREA O O OCN NCO R + Isocyanate Prepolymer H 2 N NH 2 R' Polyamine R N H N H Urea Linkage R' N H N H n

Typical formulation A side: Isocyanate component Prepolymer, (MDI, HDI, IPDI) 100% B side: Amine (Resin) component Polyether amine 40-75% Amine chain extender 15-50% Additives 0-10% System processing: Volume ratio: 1:1. Index 1.05-1.15 Application temperature & pressure: 75-80 80ºC C & 150-180 180 bar

Features and benefits of Polyurea Two component, 100% solids system, typically 1:1 volume mix Fast reactivity and cure without a catalyst Relatively moisture and temperature insensitive during application High abrasion resistance Excellent physical properties Good adhesion to variety of substrates Good low and high thermal stability

Typical uses Concrete protection Secondary containment Bridge decking Park decks Sewage installations Flat roofing Steel protection

Why develop new molecules? We are in the business of making molecules. Is there room for improvement? Adhesion Reactivity Wear and tear Processing Extending and opening new markets

JEFFAMINE amine and JEFFLINK diamine overview

PPG based polyether amines (primary) O x NH 2 R CH 2 n O NH 2 y O NH 2 z JEFFAMINE T-403 amine (x + y + z) = ~ 5-6 JEFFAMINE T-3000 amine (x + y + z) = ~ 50 JEFFAMINE T-5000 amine (x + y + z) = ~ 85

PPG based polyether amines (primary) O x NH 2 R CH 2 n O NH 2 y O NH 2 z JEFFAMINE T-403 amine (x + y + z) = ~ 5-6 JEFFAMINE T-3000 amine (x + y + z) = ~ 50 JEFFAMINE T-5000 amine (x + y + z) = ~ 85

PPG based polyether amines (primary) H 2 N O ( ) O x NH 2 JEFFAMINE D-230 amine JEFFAMINE D-400 amine JEFFAMINE D-2000 amine x ~ 3 x ~ 5 x ~ 32

PPG based polyether amines (secondary) Proprietary Huntsman catalyst technology allows high secondary amine formation with little primary or tertiary. Intrinsic reactivity drops roughly a factor of 20 for secondary compared to primary amines. Steric hindrance plays an additional role in slowing the reactivity. Cure speed (gel time) of a formulation is dependent on concentrations and inherent reactivity. Products are stable, there is no off-gassing of reversible blocking agents.

PPG based polyether amines (secondary) R NH O n O NH R JEFFAMINE SD-231 amine JEFFAMINE SD-401 amine JEFFAMINE SD-2001 amine Approximate mol weight, g/mol 315 515 2050 Approximate functionality 2 2 2 Kinematic viscosity, 25 C, cst 7 18 209 Equivalent weight, gram/eq 158 258 1025 Designed to be used in conjunction with, or to replace, aromatic or aliphatic chain extenders, or to partially replace existing primary polyether amines. Slow down reactivity Produce low viscosity prepolymers

IPDI quasi prepolymers Viscosity at 25 C (cst) 9000 8000 7000 6000 5000 4000 3000 2000 1000 0 Comparison of primary vs secondary polyetheramines in IPDI IPDI / Jeffamine D 2000 IPDI / Jeffamine SD 2001 12 13 14 15 16 17 18 19 20 NCOv (%)

H 12 MDI quasi prepolymer Viscosity at 25 C (cst) 7000 6000 5000 4000 3000 2000 1000 Comparison of primary vs secondary polyetheramines in H 12 MDI H12MDI / Jeffamine D 2000 H12MDI / Jeffamine SD 2001 0 12 13 14 15 16 17 18 NCOv (%)

PTMEG based polyether amines (primary and secondary) Poly(tetramethylene ether)glycol backbone amines - H 2 N O O a n O b ( ) ( ) ( ) NH 2 More hydrophobic, higher performance - premium soft segment

PTMEG based polyether amines (primary and secondary) JEFFAMINE THF-100 amine JEFFAMINE THF-140 amine JEEFAMINE THF-170 amine XTJ-652 (*) amine type Primary Primary Primary + Secondary Primary Fn 2 2 2.8 2 Mw 1000 1350 1700 2300 eq. weight 500 710 760 1150 viscosity 121 cst at 40 C 234 cst at 40 C 916 cst at 40 C 1245 cst at 40 C Melting point 8 C 16 C 33 C 35 C (*) experimental product

PTMEG based polyether amines (secondary) XTJ-604 (*) XTJ-605 (*) XTJ-653 (*) amine type Secondary Secondary Secondary Fn 2 2 2 Mw 1100 1430 2400 eq. weight 550 715 1200 viscosity 261 cst at 25 C 251 cst at 40 C 1150 cst at 40 C (*) experimental product

Comparing the PPG vs PTMEG based polyether amines Casting system REFERENCE XTJ-653 JEFFAMINE D 2000 amine 55 JEFFAMINE SD 401 amine 5 XTJ-653 50 BADPM 45 40 DETDA 5 Suprasec 2054 115 115 Reactivity Gel time seconds 180 120 Tack free time seconds 420 240 Mechanical properties Hardness shore D 45 44 Taber abrasion (H-18) mg loss 200 Abrasion is reduced with 70% 70

Comparing the PPG vs PTMEG based polyether amines Spray system REF XTJ-652 JEFFAMINE D 2000 amine 68 XTJ-652 68 DETDA 20 20 BADPM 12 12 MDI prepolymer (16%) 115 112 Reactivity Gel time (s) seconds 7 6 Tack free time (s) seconds 18 12

Comparing the PPG vs PTMEG based polyether amines Mechanical properties REFERENCE XTJ-652 Hardness shore D 48 49 Tear strength N/mm 83 83 Tensile at break MPa 20.3 20.1 Elongation at break % 455 407 Taber abrasion (H-18) mg loss 230 100 Abrasion is reduced with 55%

Comparing the PPG vs PTMEG based polyether amines water uptake (%) 5 days at RT 30 days at RT 150 days at RT REFERENCE 1.9 2 5.5 XTJ-652 1.5 1.5 2.5 Water uptake is reduced with 55%

JEFFLINK diamine

JEFFLINK diamine in an aliphatic system Prepolymer used Diamine used reactivity Gel time Tack free time Mechanical properties Hardness Tensile at break Elongation at break Tear strength gloss 20/60 appearance seconds seconds shore D MPa % N/mm IPDI + JEFFAMINE SD 2001 amine to NCOv 16% JEFFLINK 136 diamine JEFFLINK 754 diamine 14 6 70 155 47 35 18.2 12.3 477 444 83 57 85/85 56/55 smooth textured

JEFFLINK diamine features Colorless liquids Low viscosity Prolonged gel time Shorter dry time Variation in hardness Contribute to UV stability Product Process Property

Combining JEFFAMINE T 3000 amine with PTMEG polyether amines formulation REF 1 REF 2 T 3000 / XTJ-604 T 3000 / XTJ-605 T 3000 / XTJ-605 JEFFAMINE D 2000 amine 76 65 10 15 JEFFAMINE T 5000 amine 11 JEFFAMINE T 3000 amine 24 24 35 XTJ-604 40 XTJ-605 45 45 DETDA 24 24 16 16 20 BADPM 10 Suprasec 2054 111 111 112 114 111 Reactivity Gel time seconds 8 6 13 12 8 Tack Free Time seconds 16 12 62 42 20

Combining JEFFAMINE T 3000 amine with PTMEG polyether amines REF 1 REF 2 T 3000 / XTJ 604 T 3000 / XTJ 605 T 3000 / XTJ 605 Hardness Shore D 45 44 40 38 42 Tensile MPa 25.5 24.8 27.4 24.1 26.8 elongation % 541 561 525 510 337 Abrasion (H-18) mg loss 130 150 100 82 87 Water uptake 1 day at RT % 2.1 2.0 1.8 1.9 1.6 1 week at RT % 2.3 2.3 1.9 2.1 1.8 2 weeks at RT % Abrasion is reduced with up to 45% Water uptake is reduced with ~20%

Conclusions The new building blocks can extend your market reach Improving the abrasion resistance Reducing the water absorption Widen your formulation latitude Increase the processing latitude

What can HUNTSMAN do for you? To offer building blocks for making suitable systems towards the specialist formulators. Amine products under the JEFFAMINE amine and JEFFLINK diamine brand name MDI products under the SUPRASEC isocyanate brand name Titanium dioxide products under the TIOXIDE pigment brand name Joint projects to develop tailor made products for specific markets eg. Water proofing membranes, metal protection, To assist and offer guidance in the correct and safe use of our products EHS, ISOPA, Walk the Talk,

disclaimer Copyright 2011 Huntsman Corporation. All rights reserved. All information contained herein is provided "as is" without any warranties, express or implied, and under no circumstances shall the authors or Huntsman be liable for any damages of any nature whatsoever resulting from the use or reliance upon such information. Nothing contain in this publication should be construed as a license under any intellectual property right of any entity, or as a suggestion, recommendation, or authorization to take any action that would infringe any patent. The term "Huntsman" is used herein for convenience only, and refers to Huntsman Corporation, its direct and indirect affiliates, and their employees, officers, and directors. JEFFAMINE, JEFFLINK, SUPRASEC and TIOXIDE are registered trademarks of Huntsman Corporation or an affiliate thereof in one or more, but not all countries. Main Offices US: 500 Huntsman Way / Salt Lake City, Utah 84108 / 801-584-5700 Technical Service US: 8600 Gosling Road / The Woodlands, Texas 77381 / 281-719-7780 Main Offices Europe: Huntsman Belgium BVBA / Everslaan 45 / B-3078 Everberg, Belgium / 32-2 -758-9211 Technical Service Europe: Technical Services Representative / Everberg Office / 32-2-758-9392 Main Offices Asia Pacific Offices: Huntsman Singapore PTE / 150 Beach Road, #37-00 Gateway West / Singapore 189720 / 65 6297 3363 Technical Service Asia Pacific: Huntsman Performance Products / 61 Market Road, Brooklyn, Victoria / Australia 3012 / 61 3 9933 6666 www.huntsman.com