ITR Amorphous PLA for coating applications. TOYOBO CO.,LTD. Vylon Department Takashi Miyamoto

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1 ITR-2012 Amorphous PLA for coating applications TOYOBO CO.,LTD. Vylon Department Takashi Miyamoto

2 CONTENTS 1. About TOYOBO 2. About VYLOECOL 1Key features 2Molecular design 3Grades and each specification 4Applications (1)Packaging material (2)Ship bottom paint 3.Conclusion

3 About TOYOBO 1Date of establishment: May 3, Date of incorporation: June 26, Paid-in capital: \51,730,003,166 4Number of employees on a nonconsolidated basis: 3,238 (as of March 31,2011) 5Number of employees on a consolidated basis 10,178 (as of March 31,2011)

4 Key features VYLOECOL is amorphous polylactic acid. VYLOECOL dissolves in most of the general organic solvents due to its amorphous state. VYLOECOL shows the good adhesion property to regular polylactic acid film. Every grade provides high functionality of either pigment-dispersible binder or cross-linking property. VYLOECOL shows high-grade biodegradability and some grades are listed as the approved materials by JBPA (Japan Bio-plastic Association).

5 Molecular design PLLA Co-polymerization of D-lactic acid molecurar weight down Amorphous PLA Pigment dispersible :ionic group :D-lactic acid Tg adjustment :aliphatic momomer

6 Grades and each specification Grade Molecular weight ( 103) Tg ( ) Functional group Biobased content (wt%) Typical application BE Heat seal adhesive BE Pigment dispersion BE Cross- linking BE Cross- linking 99 Gravure ink binder 90 Primer coating 60 Dry lamination adhesive

7 Solution viscosity of VYLOECOL (Solvent: Ethyl-acetate ) 1000 ηb[dpa s] BE-400 BE NV[wt%] Solid content

8 Packaging material - Dry laminate adhesive application - Substrate: Cellulose nonwoven sheet and PLA film of other company Application: BE-910 is used for the adhesive to bond film with sheet.

9 Adhesion strength of dry lamination adhesive Substrate:25μm PLA film Coated layer thickness: 3μm Drying condition: 60 for 15min Laminate condition: 0.9m/min 29N/cm2 for 15min Cross linking agent: Colonate HX(made by Nippon Polyurethane, Aliphatic Isocyanate) Aging condition: 40 for 3days Resin grade Coated side Dry lamination adhesion strength (N/cm) PLA resin/cross linking agent (wt ratio) 100/0 100/5 100/10 100/15 BE-910 Coating to one side

10 100 The Biodegradability of Cross-linked BE ISO14855, by OWS Biodegradation (%) Time (Days) Cellulose BE91OHX5 BE91OHX10

11 Heat-sealing property; Print side Cellophane (20μm) PLA derived resin coat (1μm each) Heat-sealing property Water vapor barrier property Anti-blocking property Cellophane and coat resin both are biomass products that are derived from renewable resources, and also holds the Biodegradability.

12 GFML Comparative Table Test Item Unit GFML#300 (coating Cellophane) PL#300 (Cellophane) Coat resin PLA derivative - Thickness mm Weight g/m Tensile strength Elongation at break MD N/15mm width TD N/15mm width MD % TD % Oxygen permeability 1 cc/ m2 24h atm Moisture permeability 2 g/ m2 24hr Haze 3 % JIS K JIS Z JASCO Corporation turbidimeter These figures are test values and is not guaranteed values or standared values.

13 Ship Bottom Paint Applications This area was coated by PLA based ship bottom paints on the 16 th of Dec 1999.

14 Mechanism of Antifouling Ship Bottom Paint Layer Sea Water Typical Resin (oil-based) (-CH 2 -CH-) C=O O - M 2+ O - C=O R Self-polishing Layer (hydrolysis of resins) (-CH 2 -CH-) C=O O - Na + Antifouling Agents

15 Typical requirements for Resins 1. Resistance to cold flows 2. Suitable hydrolysis rates 3. Suitable solution viscosity

16 Cold flow test Sample resins were coated on a disk. The disk spins round at 30 knots speed. Sailing model test Good sample NG sample

17 Results of cold flow tests Good Cold Flow NG Reduced viscosity (dl/g)

18 Molecular design for Ship Bottom Paint Amorphous PLA The Hydrolysis rate is not enough -COO - M 2+ - OOC- M: Metal Key structure

19 Hydrolysis rates of PLA resins Hydrolysis rate(%) Acrilic resins(cu 2+ ) PLA ( Mg 2+ ) PLA Time (day)

20 Solution viscosity (dpa.s) Solution viscosity and ionic species Mg Ca Cu ( 1460dPa.s) Reduced viscosity(dl/g)

21 Ship Bottom Paint Applications This area was coated by PLA based ship bottom paints on the 16 th of Dec 1999.

22 Performance tests of a ship on site The Ship bottom was cheked on the 13th of Dec 2002.

23 Conclusion 1.Amorphous PLA resin is promising for coating applications. 2.Developments of biodegradable adhesives and inks have been completed. 3.There are several possibilities to commercialize PLA based Ship bottom paint and others.

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