BIO World CongressPaul J Caswell
President, Cathay Industrial BiotechMay 13,2014
The First Odd-Even Polyamide Polyamdies- A Nature MimicOdd-Even Molecular Difference Pentane Diamine (DN5), An
improvement on HMDA
Terryl: An Improved Fabric
Business Opportunity
Cathay Other Polyamide Monomers
Outline
Polyamide & Silk similar bonds, similar structure
Nylon66: Similar Beta-Structure of Peptide
PA6
PA66
Terryl
Terryl® A New Polymer
PA66
PA6 X X
Terryl XXX
XXX
Terryl® Disrupt H-Bonding Structure
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 H2N-(CH2)5-NH2 H2N-(CH2)6-NH2
% 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
-20
0
20
40
60
100% 90% 85%
Melt Point PDA Melt Point HMDA
OC
Concentration9
DN5---A Platform of BioBased Chemical
Isocyanates PA56 salt Pyridine/piperidine
Terryl® textile Engineering Plastic
PA56PE modification
DN5
The First Odd-Even Polyamide
Terryl®: An Improved Fabric Renewable Strength Similar to PA66 Improved Properties for Textile
Business Opportunity
Cathay Other Polyamide Monomers
Outline
Terryl® Production Process
Bio RM BiomimicPolymer
BiomimicProducts
Bioconversion
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 261.1 217.9 254.0Crystallization 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/cm3 1.14 1.13 1.13% Renewable ASTM D6866 % 0 0 47%
PA56 Similar to PA66 with key differences
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PA56 Mechanical Properties
0
100
200
300
400
500
PA56 PA66 PA6
ksi
Modulustensile flex
0
5000
10000
15000
20000
PA56 PA66 PA6
psi
Strengthtensile flex
-5
5
15
25
35
PA56 PA66 PA6
%
Tensile Elongation
-0.1
0.4
0.9
1.4
PA56 PA66 PA6
ft-lb
/in
Notched Izod
Clothing Samples
Spinning Strength
0.0
1.0
2.0
3.0
4.0
PET PTT PLA PA6 Terryl
Fiber Strength(cn/dtex)
Lower Density Means Less Cost in Use
Terryl® is a new biomimic material with superior performance properties:
Density
Terryl® has similar density to PA6 and PA66
Terryl® is lighter weight than polyester PTT
density (g/cm³)
PET
PTT
TerrylTM
Improved Moisture Absorbance (Saturated %)
0.0%
5.0%
10.0%
15.0%
PET PTT Terryl™
vs Polyester
0.0%
3.0%
6.0%
9.0%
12.0%
15.0%
PA6 PA66 Terryl™
vs Polyamides
Terryl® Fiber Dyability (Carpet)
20
30
40
50
60
70
80
90
100
PA6 PA66Terryl®Temperature(°C)
Fiber Ease of Dyeing (Filament)
Terryl®PA6 Bright FDY PA6
Terryl®
Dyed simultaneously in the same bath, average color fastness 4~4.5, Terryl® dyed deeper color than PA6
Terryl®--A Polymer From NatureContinuous Production, April 14,2014
The First Odd-Even polyamide
Terryl®: An improved Fabric
Business Opportunity Market wants renewable Customer voice Value Proposition
Cathay Other Polyamide Monomers
Outline
Renewable – Where Nylons are GrowingCompany Renew Line Polyamides Market RM Source
Dupont Zytel RS PA610, 1010 Specialty Castor
Arkema Rilsan T PA 11, 610, 1010, 1012
Specialty Castor
Evonik Vestamid Terra PA610, 1010, 1012
Specialty Castor
EMS Green Line PA610, 1010 PPA
Specialty Castor
Cathay Terryl
PA56, PA5X
PA56, 510, 512,514, 612,
Textile, Injection Molded, Specialty
Plant sugar, Palm oil, Castor oil
Cathay has the broadest source of renewable polyamides
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Voice of the Customers
Application Status
Customer 1 Textile Met all needs. Negotiating a 20,000 MT per year supply
Customer 2 Engineering Polymers Positive initial DN5 test. Currently testing multi-MT.
Customer 3 Carpet
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
0%
10%
20%
30%
40%
50%
60%
70%
80%
90%
100%
PA6 PA66 Terryl
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).
Cathay Biobased Diamine is Cost Competitive
Terryl® & All Renewable Cost Advantages
otherBio PEPLA
PE
PA6PA56PA66
dashed line shows potential improved future cost
Polyester fiber cost Polyamide fiber cost
The first Odd-even Polyamide
Terryl®: An Improved Fabric
Business Opportunity
Cathay Other Polyamide Monomers Polyamide 5X
Outline
Broad Innovative Product Range
1,11-Undecanedioic Acid HOOC(CH2)9COOH1,12-Dodecanedioic Acid HOOC(CH2)10COOH1,13-Brassylic Acid HOOC(CH2)11COOH1,14-Tetradecanedioic Acid HOOC(CH2)12COOH1,15-Pentadecanedioic Acid HOOC(CH2)13COOH1,16-Hexadecanedioic Acid HOOC(CH2)14COOH1,18-Octadecanedioic Acid HOOC(CH2)16COOH1,5 Pentane Diamine H2N(CH2)5NH2
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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
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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
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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.•