BIO World Congress Paul J Caswell President, Cathay Industrial Biotech May 13,2014
Outline The First Odd-Even Polyamide Polyamdies- A Nature Mimic Odd-Even Molecular Difference Pentane Diamine (DN5), An improvement on HMDA Terryl: An Improved Fabric Business Opportunity Cathay Other Polyamide Monomers
Polyamide & Silk similar bonds, similar structure
Nylon66: Similar Beta-Structure of Peptide
Terryl A New Polymer PA6 PA66 Terryl
Terryl Disrupt H-Bonding Structure PA66 PA6 X X Terryl X X X X X X
Cathay C-Bio DN5 Technical Data DN5 HMDA CAS No. 462-94-2 124-09-4 % Renewable (ASTM D6866) 100% 0% Molecular weight 102 116 Formula H 2 N-(CH 2 ) 5 -NH 2 H 2 N-(CH 2 ) 6 -NH 2 % NH2 31% 28% Appearance clear liquid clear solid Melting point ( C) 9 41 pka1 10.05 10.24 pka2 10.93 11.02 ph 5% solution 12.6 12.4 8% less diamine needed in polyamide with DN5
DN5-Renewable from Plant Sugars 8
Lower Melt Temperature than HMDA 60 Melt Point PDA Melt Point HMDA O C 40 20 0-20 100% 90% 85% Concentration 9
DN5---A Platform of BioBased Chemical DN5 Isocyanates PA56 salt Pyridine/piper idine PE modification PA56 Terryl textile Engineering Plastic
Outline The First Odd-Even Polyamide Terryl : An Improved Fabric Renewable Strength Similar to PA66 Improved Properties for Textile Business Opportunity Cathay Other Polyamide Monomers
Terryl Production Process Bio RM Bioconversion Biomimic Polymer Biomimic Products
45% Renewable Carbon 13
More Renewable Carbon Than PTT Terryl is a new generation of nylon, inspired by nature, renewable, low carbon, environmentally friendly. Renewable Carbon Content (according to ASTM D6866) Terryl offers: Higher biobased content Lower overall cost Terryl PTT
Cathay PA56 Properties Test Method Unit PA66 PA6 PA56 Decomposition temperature TGA C 424.7 426.3 424.3 Melting point TGA C 261.1 217.9 254.0 Crystallization temperature DSC C 222.3 193.7 213.5 Notched Izod Impact ASTM D256 J/m 42.4 41.8 35.3 Tensile Modulus ASTM D638 Mpa 3087.2 3010.2 2940.1 Tensile Strength at Break ASTM D638 Mpa 75.4 72.4 69.8 Elongation at Break ASTM D638 % 17.4 8.0 15.7 Flexural Modulus ASTM D790 Mpa 2851.8 2600.0 2870.1 Flexural Strength ASTM D790 Mpa 124.3 118.0 125.6 Density ASTM D792 g/cm 3 1.14 1.13 1.13 % Renewable ASTM D6866 % 0 0 47% PA56 Similar to PA66 with key differences 15
PA56 Mechanical Properties 500 Modulus tensile flex 20000 Strength tensile flex 400 15000 ksi 300 200 psi 10000 100 5000 0 PA56 PA66 PA6 0 PA56 PA66 PA6 35 Tensile Elongation 1.4 Notched Izod % 25 15 5 ft-lb/in 0.9 0.4-5 PA56 PA66 PA6-0.1 PA56 PA66 PA6
Clothing Samples
Spinning Strength Fiber Strength(cn/dtex) 4.0 3.0 2.0 1.0 0.0 PET PTT PLA PA6 Terryl
Lower Density Means Less Cost in Use Terryl is a new biomimic material with superior performance properties: density (g/cm³) Density Terryl has similar density to PA6 and PA66 PET Terryl is lighter weight than polyester PTT PTT Terryl TM
Improved Moisture Absorbance (Saturated %) 15.0% vs Polyester 15.0% vs Polyamides 12.0% 10.0% 9.0% 5.0% 6.0% 3.0% 0.0% PET PTT Terryl 0.0% PA6 PA66 Terryl
Terryl Fiber Dyability (Carpet) Temperature( C) 20 Terryl PA6 PA66 30 40 50 60 70 80 90 100
Fiber Ease of Dyeing (Filament) Terryl PA6 Bright FDY Terryl PA6 Dyed simultaneously in the same bath, average color fastness 4~4.5, Terryl dyed deeper color than PA6
Terryl --A Polymer From Nature Continuous Production, April 14,2014
Outline The First Odd-Even polyamide Terryl : An improved Fabric Business Opportunity Market wants renewable Customer voice Value Proposition Cathay Other Polyamide Monomers
Renewable Where Nylons are Growing Company Renew Line Polyamides Market RM Source Dupont Zytel RS PA610, 1010 Specialty Castor Arkema Rilsan T PA 11, 610, 1010, 1012 Evonik Vestamid Terra PA610, 1010, 1012 EMS Green Line PA610, 1010 PPA Cathay Terryl PA56, 510, 512, 514, 612, PA56, PA5X Specialty Specialty Specialty Textile, Injection Molded, Specialty Castor Castor Castor Plant sugar, Palm oil, Castor oil Cathay has the broadest source of renewable polyamides 25
Voice of the Customers Customer 1 Customer 2 Customer 3 Application Textile Engineering Polymers Carpet Status Met all needs. Negotiating a 20,000 MT per year supply Positive initial DN5 test. Currently testing multi-mt. Initial spinning and performance of PA56 was good. Ordered 70 kg for next stage test, expect commercial launch Q2-3 2015.
中国生物基尼龙的发展空间 Terryl Customer Value Proposition 100% 90% RM Cost Spin Cost Available Margin Current China Situation PA 6 Textile has no margin PA66 Textile has margin, no RM supply Terryl offers margin for Cathay & Customer (assume sale price at PA66 price). 80% 70% 60% 50% 40% 30% 20% 10% 0% PA6 PA66 Terryl
Cathay Biobased Diamine is Cost Competitive
Terryl & All Renewable Cost Advantages dashed line shows potential improved future cost PLA other Bio PE PA66 PA56 PA6 PE Polyester fiber cost Polyamide fiber cost
Outline The first Odd-even Polyamide Terryl : An Improved Fabric Business Opportunity Cathay Other Polyamide Monomers Polyamide 5X
3 1 Broad Innovative Product Range 1,11-Undecanedioic Acid 1,12-Dodecanedioic Acid 1,13-Brassylic Acid 1,14-Tetradecanedioic Acid 1,15-Pentadecanedioic Acid 1,16-Hexadecanedioic Acid 1,18-Octadecanedioic Acid HOOC(CH 2 ) 9 COOH HOOC(CH 2 ) 10 COOH HOOC(CH 2 ) 11 COOH HOOC(CH 2 ) 12 COOH HOOC(CH 2 ) 13 COOH HOOC(CH 2 ) 14 COOH HOOC(CH 2 ) 16 COOH 1,5 Pentane Diamine H 2 N(CH 2 ) 5 NH 2
Ordinary and Specialty Nylons
Renewable Polyamides Possible from Cathay Monomers PA Renewable % Diamine Diacid PA56 47% 5 6 PA510 100% 5 10 PA511 36% 5 11 PA512 34-100% 5 12 PA513 32-100% 5 13 PA612 up to 63% 6 12 PA514 31-100% 5 14 PA1012 46-100% 10 12 PA1212 up to 100% 12 12 33
Summary Terryl is a renewable polymer with performance advantages: Terryl is the first large scale odd-even polyamide More open amide bonds increases dyability Odd/even structure improves moisture absorbance for better fabric feel Terryl is the first renewable polyamide to compete with PA66. Polyamide 5X offers new opportunities to the nylon market Cathay has supplied C11-C15 long chain diacids for over 10 years Cathay now offers pentane diamine monomer: renewable with lower melt point than HMDA
Thank You 35
Talking Points Terryl is a nylon, similar to nylon 66, but is produced from 47% sustainable material. Terryl can be produced from any plant sugar or starch. At Cathay our first facility will use corn sugar. Cathay is working on biomass based sugar, using agriculture waste material, and plans a gradual conversion, as the technology develops. The timeline is still uncertain. 45% of the carbon in Terryl is from plant sources. This plant-based CO2 from the renewable feedstock has been removed from the atmosphere, not extracted from oil. Terryl is renewably based, but not biodegradable. The CO2 removed from the atmosphere will be locked up in Terryl for a long time in its use application, or when it is recycled. Finally, if Terryl is burnt, it would release 960 kilograms less oil-based CO2 per MT of nylon. Terryl is fully recyclable, like all polyamides. Terryl is a performance plastic, not a fuel. If all of the nylon in the world was Terryl and made only from corn then it would use 1.5% of the world s corn. By comparison, US ethanol for 10% of the US fuel uses 14% of the world s corn. Corn is not a stranger to industrial chemicals Many industrial products are made from corn starch. Most finished paper is coated with this starch. Terryl can and will also be made from sugar cane or industrial starch crops like cassava.