Improved polyester coating resins from carbohydrate derived, biobased building blocks Bas van Leeuwen Technical Marketing Specialist NVVT Studiemiddag Nieuwegein, 28 mei 2013 Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 1 Content • Introduction • Biobased building blocks • Saturated polyesters • Resin • Non-air drying industrial coating • Alkyd • Resin • Air drying architectural coating • Summary Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 2 Purac profile • Focus on: • Natural food preservation • Biobased building blocks & chemicals • Monomers for bioplastics • 80 years of experience in the development, production and marketing of natural Lactic acid based chemicals • Global sales network & manufacturing footprint • Headquarters in Gorinchem, The Netherlands • 2011 turnover € 407 million • Part of CSM: • A Dutch multinational • Listed at Amsterdam Stock Exchange Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 3 Our ‘pure by nature’ concept Raw materials from nature ▪ ▪ ▪ ▪ Beet sugar Cane sugar Corn starch Tapioca starch Processes based on nature ▪ Fermentation ▪ Crystallization ▪ Filtration Products compatible with nature ▪ Environmentally friendly ▪ Human friendly ▪ Biodegradable ▪ Low CO2 footprint Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 4 Purac: Product portfolio Food market: ▪ Natural preservation solutions ▪ Taste & Nutrition solutions Chemical & Pharma markets: ▪ Lactic acid, Lactides and Lactic acid derivatives ▪ Biobased building blocks Bioplastics markets: ▪ L-Lactide monomers for PLA based bioplastics ▪ D-Lactide monomers for PLA based bioplastics Medical markets: ▪ Lactide, glycolide and caprolactone monomers ▪ Polymers for medical devices and drug delivery Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 5 Content • Introduction • Biobased building blocks • Saturated polyesters • Resin • Non-air drying industrial coating • Alkyd • Resin • Air drying architectural coating • Summary Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 6 Biobased building blocks - Monomers Lactic acid C3 Lactide Lactate esters O OR Fermentation OH C4 Succinic acid (JV with BASF) Cx Under Development Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 7 Lactic acid – Current process Lime Sulphuric acid Energy Lactic Sugar fermentation Acidification Purification Biomass Gypsum Co-Products Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party acid 8 CO2 Balance Lactic Acid Cradle to gate Sugar Sugar production Sugar Transport Aux Chemical Steam Electricity Total Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 9 Lactic acid – Gypsum free process Lime Sulphuric acid Energy Lactic “Sugar” fermentation Acidification Purification Biomass Gypsum Co-Products Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party acid 10 CO2 Balance Lactic Acid Cradle to gate; renewable utilities and gypsum free process Sugar Sugar production Sugar Transport Aux Chemical Steam Electricity Total Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 11 Lactide as biobased building block in polyester resin Improvement CO2-footprint Balance of hardness / flexibility Reduced reaction water Crystallinity Stiffness Gloss Adhesion Lactide Renewable content Higher fatigue resistance Availability Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 12 Content • Introduction • Biobased building blocks • Saturated polyesters • Resin • Non-air drying industrial coating • Alkyd • Resin • Air drying architectural coating • Summary Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 13 Saturated polyester resins • Saturated polyesters are of increasing importance in coatings • Greater demand on: • • • • Hardness Flexibility Impact strength Chemical resistance • Driver towards Green chemistry • Carbon footprint • Independence of fossil resources based raw materials Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 14 Lactide modified saturated polyester resins • Polyester resin formulation • Modification of the formulation with 20% of Lactide • Replacing a mixture of di functional glycol / aliphatic diacids Enamel Lactide modified enamel Adipic acid √ Phthalic anhydride √ NPG √ TMP √ √ Lactide - 20% √ Theoretical Acid value (mg KOH/g) 10 OH value (mg KOH/g) 160 Mw (avg) 1008 Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 15 Lactide modified saturated polyester resins • Range of saturated polyester resin formulation • Modification of the formulations with 20% of Lactide • Replacing a mixture of di functional glycol / aliphatic diacids • Saturated polyester for enamel coatings • Theoretical Mw of 1000 • Saturated polyester for coil coatings • Theoretical Mw of 2800 • Saturated polyester for performance enamel coatings • Theoretical Mw of 1300 Enamel Enamel Modified Coil Coil Modified Perf. Enamel Perf. Enamel Modified Acid value (mg KOH/g) 10 10 10 10 10 10 OH value (mg KOH/g) 157 155 33.8 34 110 110 1008 1008 2774 2767 1303 1338 Analytical data Mw (avg) Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 16 Impact on CO2 footprint • Modification with Lactide reduces the CO2-footprint of the pure resin • Based on raw materials Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 17 Characteristics of the resins • Modification with Lactide reduces the viscosity of the resins • Comparable molecular weight Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 18 Characteristics of the resins • Enabling higher solid formulations through the reduced viscosity of the Lactide modified resins Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 19 Characteristics of the resins • Modification with Lactide reduces the viscosity of the resins • Retention of the rheological behaviour of the polymer resin Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 20 Characteristics of the resins • Influence of the Lactide % on the viscosity of the resins Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 21 Lactide modified saturated polyester resins in coatings • Screening within a saturated polyester / melamine coating system: • Curing cycle 15 min at 160°C with Cymel 303LF • Applied 50 µ wet • Evaluation of the coating on: • Mechanical properties • Chemical resistance Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 22 Characteristics of the coatings - Mechanical properties • Modification with Lactide enhances the hardness while maintaining flexibility Hardness König (s) 300 250 200 150 100 50 0 Surface hardness Reference Lactide modified Conical bend (diameter mm) Increased hardness 6 5 Flexibility Reference Lactide modified 4 3 2 1 0 Increased flexibility Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 23 Characteristics of the coatings - Mechanical properties • Overall mechanical properties • • • • Improvement on hardness both pencil and König Retention of flexibility Impact resistance Adhesion improvement • Formulation dependent Enamel reference Enamel lactide modified 0= not effected …5= fail 5 4 3 2 1 0 Steel Aluminium Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 24 Characteristics of the coatings - Outdoor stability • Modification with Lactide exhibits a comparable outdoor behaviour as the reference coating. • Modification with 30% Lactide performs less in this formulation Gloss retention 20° 100 90 80 Test method: ISO 4892-2A Cycle: 102min. Light / 18 min. Light+ss 70 Initial Reference enamel coating 200h 10% Lactide 500h 20% Lactide 1000h 30% Lactide Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 25 Content • Introduction • Biobased building blocks • Saturated polyesters • Resin • Non-air drying industrial coating • Alkyd • Resin • Air drying architectural coating • Summary Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 26 Alkyd resins • Alkyds still an important role in coatings. • Greater demand on: » » » » » Hardness Flexibility Impact strength Chemical resistance Solvent content • Driver towards Green chemistry. • Carbon footprint • Independence of fossil resources based raw materials Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 27 Lactide modified long oil alkyd resins • Modification of the formulations with 10% of Lactide • Replacing a mixture of di functional glycol / diacids • Soya fatty acid based long oil alkyd Long oil alkyd Lactide mod. Long oil alkyd Acid value (mg KOH/g) 10 10 OH value (mg KOH/g) 27 29 3621 3621 Oil length (%) 68 65 Alkyd constant 1.02 1.02 Analytical data Mw (avg) Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 28 Impact on CO2 footprint • Modification with Lactide reduces the CO2-footprint of the pure resin • Based on raw materials 80 Kg CO2 eq / Kg 0.39 0.38 75 0.37 0.36 0.35 70 0.34 0.33 65 0.32 0.31 0.3 Renewable content (%) 0.4 60 Long oil alkyd Lactide modified long oil alkyd Renewable content Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 29 Characteristics of the resins • Modification with Lactide reduces the viscosity of the resins • Comparable molecular weight Viscosity @ RT (cP) 500 450 400 350 300 250 200 150 100 50 0 Long oil alkyd Lactide modified long oil alkyd 85% in xylene Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 30 Lactide modified long oil alkyd resins • Coating system • Combi dryer: Borchers Dry 0133 • Applied 60 µ wet • Evaluation of the coating on: • Mechanical properties • Chemical resistance Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 31 Characteristics of the coatings - Mechanical properties • Hardness development in time • Lactide modification gives a slightly harder coating and maintaining a similar hardness build-up in time 35 König hardness (s) 30 25 20 15 10 Long-oil alkyd reference 5 Lactide modified long-oil alkyd 0 0 5 10 15 20 25 30 Time (days) Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 32 Characteristics of the coatings - Mechanical properties • Drying time • Lactide modification improves the drying time Lactide modified long oil alkyd Long oil alkyd 0 leveling 2 4 basic trace 6 ripped film 8 10 surfac trace Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 12 Dry 33 Characteristics of the coatings - Chemical properties • Overall chemical properties • Comparable chemical resistance • Influence of Lactide modification on forced yellowing • 4 wks at 50°C in the dark Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 34 Content • Introduction • Biobased building blocks • Saturated polyesters • Resin • Non-air drying industrial coating • Alkyd • Resin • Air drying architectural coating • Summary Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 35 Summary • Purac’s biobased building blocks have a good fit in resins. • The modification of saturated polyesters resins with Lactide enables: • Improvement of the CO2-footprint • Increase biocontent • Balancing performance in melamine and PU-coatings • • • • Lower resin viscosity for higher solid formulations Improved hardness while maintaining flexibility Adhesion improvement Chemical resistance Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 36 Summary • The modification of alkyd resins with Lactide enables: • Improvement of the CO2-footprint • Increase renewable content • Balancing performance • Lower resin viscosity for higher solid formulations • Gloss and gloss retention after yellowing in the dark • Hardness and flexibility (Industrial) • Tune the drying time behaviour (Architectural) Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 37 Bas van Leeuwen Technical Marketing Specialist Biobased Building Blocks P +31 183 713 044 M +31 615 959 035 bas.van.leeuwen@purac.com Disclaimer: Nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the described materials or processes in violation of existing or future patent of Purac or any party 38
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