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BIO World Congress Paul J Caswell President, Cathay Industrial Biotech May 13,2014
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Page 1: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

BIO World CongressPaul J Caswell

President, Cathay Industrial BiotechMay 13,2014

Page 2: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 3: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Polyamide & Silk similar bonds, similar structure

Page 4: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Nylon66: Similar Beta-Structure of Peptide

Page 5: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

PA6

PA66

Terryl

Terryl® A New Polymer

Page 6: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

PA66

PA6 X X

Terryl XXX

XXX

Terryl® Disrupt H-Bonding Structure

Page 7: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 8: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

DN5-Renewable from Plant Sugars

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Page 9: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Lower Melt Temperature than HMDA

-20

0

20

40

60

100% 90% 85%

Melt Point PDA Melt Point HMDA

OC

Concentration9

Page 10: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

DN5---A Platform of BioBased Chemical

Isocyanates PA56 salt Pyridine/piperidine

Terryl® textile Engineering Plastic

PA56PE modification

DN5

Page 11: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 12: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Terryl® Production Process

Bio RM BiomimicPolymer

BiomimicProducts

Bioconversion

Page 13: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

45% Renewable Carbon

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Page 14: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 15: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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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Page 16: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 17: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Clothing Samples

Page 18: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Spinning Strength

0.0

1.0

2.0

3.0

4.0

PET PTT PLA PA6 Terryl

Fiber Strength(cn/dtex)

Page 19: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 20: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 21: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Terryl® Fiber Dyability (Carpet)

20

30

40

50

60

70

80

90

100

PA6 PA66Terryl®Temperature(°C)

Page 22: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 23: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Terryl®--A Polymer From NatureContinuous Production, April 14,2014

Page 24: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

The First Odd-Even polyamide

Terryl®: An improved Fabric

Business Opportunity Market wants renewable Customer voice Value Proposition

Cathay Other Polyamide Monomers

Outline

Page 25: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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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Page 26: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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.

Page 27: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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).

Page 28: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Cathay Biobased Diamine is Cost Competitive

Page 29: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Terryl® & All Renewable Cost Advantages

otherBio PEPLA

PE

PA6PA56PA66

dashed line shows potential improved future cost

Polyester fiber cost Polyamide fiber cost

Page 30: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

The first Odd-even Polyamide

Terryl®: An Improved Fabric

Business Opportunity

Cathay Other Polyamide Monomers Polyamide 5X

Outline

Page 31: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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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Page 32: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Ordinary and Specialty Nylons

Page 33: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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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Page 34: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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

Page 35: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

Thank You

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Page 36: BIO World Congress › sites › default › files › legacy › bioorg... · 2014-06-30 · If all of the nylon in the world was Terryl and made only from corn then it would use

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.•


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