Huntsman Corporation · NYSE:HUN
Huntsman — Technical Presentation (June 2007)
17 slides from Huntsman's technical presentation, June 2007
Slide 1: 'Spanning the Gulf' Between Primary Amine and Hydroxyl Reactivity
‘Spanning the Gulf’ Between Primary Amine and Hydroxyl Reactivity, New Secondary Aliphatic Amines for the Formulator’s Toolbox R1 NH R OH R NH2 R2 Mark Posey and Ken Hillman Huntsman – Advanced Technology Center Originally presented at 2005 Polyurea Development Association Annual Conference, updated
Slide 2: The Problem
The Problem • OH reaction with isocyanate is slow and usually requires catalyst. Water competes with OH for isocyanate reaction. • Primary amine is fast reacting, time for leveling and good adhesion is needed. • Chain extenders and aspartic esters are cost prohibitive for some applications. • The ne
Slide 3: The Technology
The Technology • Proprietary Huntsman catalyst technology allows high secondary amine formation with little primary or tertiary. O R R O NH y NH NH O R n R O O R NH NH x z • Intrinsic reactivity drops roughly a factor of 20 for secondary compared to primary amines. – Steric hindrance plays an additi
Slide 4: Huntsman's New Secondary Polyetheramines
Huntsman’s New Secondary Polyetheramines JEFFAMINE® SD-231 JEFFAMINE® SD-401 JEFFAMINE® SD-2001 JEFFAMINE ST-404 (XTJ-586)* ® Secondary Version of D-230 D-400 D-2000 T-403 Approximate Functionality 2 2 2 3 Density, 25°C, g/cm3 0.885 0.921 0.978 0.923 Kinematic Viscosity, 25°C, cSt 7 18 209 46 Total
Slide 5: Potential Uses for Secondary Polyetheramines
Potential Uses for Secondary Polyetheramines • Polyurea Chain Extender - Aliphatic AND Aromatic Systems – Used in conjunction with, or to replace, existing chain extenders. • Polyurethane/Polyurea hybrids • When using the amine as a reactant, prevents more than one reaction at each amine site. • Iso
Slide 6: Viscosity Reduction in Isocyanate Prepolymers
Viscosity Reduction in Isocyanate Prepolymers Hydrogen Bonding in Ureas Hydrogen Bonding in Ureas from Primary Amines from Secondary Amines O O R C R R C R N N N N H H H R2 O O R C R R C R N N N N H H H R2 2005 PDA Annual Conference, March 8-10, 2005, Biloxi, MS 6
Slide 7: IPDI Quasi-prepolymer Viscosity
IPDI Quasi-prepolymer Viscosity 9000 8000 IPDI/D-2000 7000 IPDI / SD-2001 Kinematic Viscosity at 25C, cSt IPDI / D-2000 / 10% PC 6000 5000 4000 3000 2000 1000 0 40 45 50 55 60 Wt% IPDI in Prepolymer Formation 2005 PDA Annual Conference, March 8-10, 2005, Biloxi, MS 7
Slide 8: H12MDI Quasi-prepolymer Viscosity
H12MDI Quasi-prepolymer Viscosity 7000 H12MDI / D-2000 H12MDI / SD-2001 6000 Kinematic Viscosity at 25C, cSt 5000 4000 3000 2000 1000 0 40 45 50 55 60 65 Wt% H12MDI in Prepolymer Formation 2005 PDA Annual Conference, March 8-10, 2005, Biloxi, MS 8
Slide 9: Aliphatic Coatings Formulations
Aliphatic Coatings Formulations Both Formulations 1:1 Volume Ratio at ~14.5% NCO Reference No. 8276-63-1 8349-96 A Side IPDI 45 45 JEFFAMINE® D-2000 amine 55 0 JEFFAMINE® SD-2001 amine 0 55 B Side JEFFAMINE® D-2000 amine 50.4 49 JEFFAMINE® T-5000 amine 8.6 10 JEFFLINK® 754 chain extender 34 36 TiO2
Slide 10: High Hardness Aliphatic Formulations
High Hardness Aliphatic Formulations All Formulations 1:1 Volume Ratio HDI trimer (~21.7% NCO) Reference No. 8276-68 8276-71 8349-31 JEFFAMINE® D-2000 amine 15 10 10 ® JEFFAMINE D-400 amine 20 0 0 ® JEFFAMINE SD-401 amine 0 25 0 Secondary Amine X 0 0 30 ® JEFFLINK 754 chain extender 60 65 45 TiO2 5
Slide 11: Modified Aspartic Ester Formulations
Modified Aspartic Ester Formulations HDI trimer/JEFFAMINE® SD-2001 Prepolymer (85/15 wt%), ~17.4% NCO, 1:1 Volume Ratio Reference No. 8349-24 8349-25 JEFFAMINE® SD-401 amine 0 20 DESMOPHEN® NH1420 resin 83 60 JEFFLINK® 754 curing agent 12 15 TiO2 5 5 Tensile Strength, psi 4488 2349 Max Elongation, %
Slide 12: Partial Replacement of Aromatic Chain Extenders
Partial Replacement of Aromatic Chain Extenders • Aliphatic amines react too fast to replace aromatic amines in aromatic formulations, right? Wrong. • The following tables shows the effect of replacing aromatic amines with secondary aliphatic amines (in small amounts). • Can improve flexibility and/
Slide 13: High Hardness Aromatic Formulations
High Hardness Aromatic Formulations All Formulations 1:1 Volume Ratio with SUPRASEC® 9549 isocyanate (~19.4%NCO) Reference No. 8314-9 8314-10 8314-11 JEFFAMINE® D-2000 amine 23 27 25 JEFFAMINE® T-5000 amine 9 9 9 ETHACURE® 100 curing agent 18 18 17 JEFFAMINE® SD-231 amine 0 0 17 JEFFAMINE® SD-401 am
Slide 14: Replacement of UNILINK 4200 additive with Secondary Amines in Aromatics
Replacement of UNILINK® 4200 additive with Secondary Amines in Aromatics All Formulations with RUBINATE® 9480 Aromatic Isocyanate (~15.5%NCO) Reference No. 8276-72 8314-12 8276-93 8276-92 JEFFAMINE® D-2000 amine 53 55 48 53 ® JEFFAMINE T-5000 amine 10 10 10 10 ® ETHACURE 100 curing agent 22 22 22 22
Slide 15: Summary
Summary • Secondary polyetheramines allow the efficient formation of low viscosity prepolymers with properties equivalent to primary polyetheramines or polyols. • Secondary amines allow the formation of high hardness coatings, with good flexibility, at a reasonable cost. • Secondary polyetheramines
Slide 16: Commercial Availability
Commercial Availability • Developmental quantity samples available now of JEFFAMINE® SD-231, JEFFAMINE® SD-401, JEFFAMINE® ST-404 (XTJ-586), JEFFAMINE® SD-2001. • Patent applications have been filed on the production method and use of these products. • Technical Data Sheets are available at www.hunt
Slide 17: Formulations Disclaimer
Formulations Disclaimer 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 conta