Caprolactone chemistry

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2 Caprolactone chemistry Tailor-made polymerization by: Ring-opening polymerization Initiator H-functionality to react with f.x. NC or melamine crosslinkers General properties Very low acid number (<1 mg KH/g) Exactly defined functionality Narrow molecular weight distribution Low viscosity generate low VC Due to very controlled ring-opening polymerization

3 Polycaprolactones General structures Perstorp has produced caprolactone monomer for 40 years biggest producer of caprolactones in the world Supply caprolactone polyols for a wide range of applications Coatings PUDs PU elastomers PU adhesives Grades for crosslinked coatings Functionality 2-4 Mw g/mol H-content % { } CH 2 CH 2 CH 2 H n { } n { } n H Trifunctional polycaprolactone H H (H 2 C) 5 (H 2 C) 5 Difunctional polycaprolactone H n n (CH 2 ) 5 H n (CH 2 ) 5 H Tetrafunctional polycaprolactone n

4 Capa Polyols - ur offer Caprolactones are aliphatic, liquid, low viscosity polyols suitable as reactive diluents with: Very low acid number (<1 mg KH/g) Standard grades - workhorses Product Type Mw H-value (mg KH/g) Exactly defined functionality H % Viscosity C) Recommendations Capa 2054 Diol K HMMM SB Capa 2085 Diol (@ 35 C) 1K HMMM SB Capa 3050 Triol ,190 2K PUR WB & SB Capa 3091 Triol ,246 2K PUR & 1K HMMM SB Capa 4101 Tetrol 1, ,850 2K PUR WB & SB Special grades - for high functionality / dense crosslinking Product Type Mw H-value (mg KH/g) H % Viscosity C) Recommendations Capa 2043 Diol K PUR & 1K HMMM WB & SB Capa 3031 Triol K PUR WB & SB Special grades - for SB 2K PUR soft feel formulations Product Type Mw H-value (mg KH/g) H % Viscosity C) Remarks Capa 7203 Diol 2, Polycarbonate co-polymer Capa 8025D Diol 2, Polylactide co-polymer

5 Application studies Properties of hydroxylfunctional components Solid content Viscosity H-content Mw Functionality wt-% C % g/mol Acrylic polyol 75 5, * n.a. n.a. Polyester polyol 78 6, * n.a. n.a. Capa , Capa , , Acrylic emulsion * n.a. n.a. * n solids

6 2K PUR Solventborne formulations Straight forward additions, if pigmented formulations, preferably in grinding part Principle of formulations *Used to set final 22 sec in DIN Cup 4 All acrylic Ref polyester Mod. A Mod. B Mod. C Mod. D PART A Capa 3050 Capa 3050 Capa 3050 Capa 4101 Acrylic polyol Polyester polyol 7.68 Capa Capa Solvent mixture Additive package DBTL (1% in BuAc) Total: PART B Low viscosity HDI-trimer Solvent mixture* In Mod. A - Capa 3050 replace reference polyester on weight basis In Mod. B - Capa 3050 replace reference polyester to match H content In Mod. C Double amount of Capa 3050 in order to stress influence In Mod. D - Capa 4101 replace reference polyester to match H content

7 g/l Solventborne formulations VC All acrylic VC at spray viscosity Ref Polyester Mod. A Mod. B Mod. C Mod. D VC reduced in formulation already considered to be High solid Even more pronounced when doubling amount of polycaprolactone (Mod. B Mod. C) Important to use low viscosity NC crosslinkers Due to relatively high H-number

8 Weight loss (mg) Solventborne formulation Abrasion resistance All acrylic Ref Polyester Mod. A Mod. B Mod. C Mod. D Abrasion test on steel panels, 500g load, 1000 cycles A combination of high crosslink density, low Tg and semicrystalline caprolactone segments give the coating a rubbery, elastomeric character

9 cm*kg Solventborne formulation Impact resistance All acrylic Impact resistance at -25 C Ref Polyester Aliphatic, low Tg properties of caprolactone segments improve impact resistance at low temperature Also has an impact of stone chip resistance and rain erosion resistance Mod. A Mod. B Mod. C Mod. D Indirect impact Direct impact Especially pronounced effect on indirect (reverse) impact

10 Solventborne formulation Scratch resistance All Acrylic Ref polyester Mod. A Mod. B Mod. C Mod. D Plastic / Plastic transition 10 g 10 g 10 g 10 g 10 g 10 g Plastic / Fracture transition 140 g 140 g 180 g 220 g 230 g 200 g Low Tg of caprolactone segments reduce brittleness and risk of creating permanent scratch. Semi-crystallinity introduced by caprolactones also reduces internal stress and increases viscoelastic properties which improve reflow properties. Principle of Taber Model 550 Rotation speed 0.5 rpm: the coating is scratched by the indenter with a progressive increased load. Traces left by the indenter are evaluated on the film: Smooth scratch: Plastic deformation of the film which recovers by a slow reflow at temperature higher than Tg Permanent scratch: Fracture deformation of the film which remains even after slow reflow at T > Tg Measured: Critical load for plastic/fracture transition

11 Relative gloss decrease, % Solventborne formulation Accelerated weathering 120 Accelerated wheathering (QUV-B) gloss hours All acrylic Ref Polyester Mod. A Mod. B Mod. C Mod. D Excellent stability due to aliphatic structure with low acid number Even more pronounced with an increaced amount of polycaprolactones

12 Force in N Solventborne formulation Flexibility40 Mod. D 30 All acrylic Mod. A 20 Mod. B Ref Polyester 10 Mod. C Strain in% Effect on strain is emphasized by result from double amount Possible to find a balance between strength and elongation

13 Waterborne formulations Polycaprolactones are essentially hydrophobic Not possible to dissolve in water Low molecular weight polycaprolactones are still suitable to add in systems based on acrylic emulsions due to: Low viscosity Relatively high H-number Excellent compatibility with acrylic polymer Migrate into hydrophobic emulsion droplets - Utilizing shear force - Utilizing existing emulsifiers Case sensitive

14 Waterborne formulation Emulsification Frequenny Mixing with an dissolver Effect of additions of 3-functional polycaprolactone (wt-%) on particle size distribution of an uncured acrylic emulsion ,01 0, % - stable peak Particle size [µm] 32% - peak is moving towards higher particles 40% - distinct bimodal particle size distribution instant separation Without Capa Add 8% Capa 3050 Add 13% Capa 3050 Add 16% Capa 3050 Add 32% Capa 3050 Add 40% Capa 3050

15 2K PUR Waterborne formulations 8% 8% Products All acrylic Capa 3050 Capa % Capa % Capa 4101 Acrylic emulsion Capa Capa Defoamer Wetting agent Water (demin.) Water dispersable NCcrosslinker BGA Water (demin.) * Solid content 42.1 % 43.1 % 43.5 % 44.6 % 44.3 % VC g/l g/l g/l g/l g/l NC/H = 1.2 *used to set viscosity at 25s DIN4

16 lvc (g/liter) Waterborne formulations Effect on VC Capa 3050 Capa % Capa on total resins Replacement of acrylic polyol emulsion by polycaprolactones leads to a VC reduction of the formulation up to 10%.

17 Time (min) Waterborne formulations Influence on drying time Drying time, T % 8% 13% Level of addition (wt-%) Capa 3050 Capa 4101 Replacement of 8% of the acrylic polyol emulsion by 3-functional polycaprolactone has limited influence on the drying time of the coating

18 Waterborne formulations Gloss & Haze 20 Haze % 8% 13% % 8% 13% Capa 3050 Capa 4101 Level of addition (wt-%) Level of addition (wt-%) Significant improvement of gloss and haze are combination of: Perfect compatibility Low viscosity improve flow and levelling (longer open time) improve film formation polycaprolactones act as REACTIVE CALESCING AGENT

19 Inch*Ibs Waterborne formulations Impact resistance Reverse impact resistance (ASTM) % 8% 13% Level of addition (wt-%) Capa 3050 Capa 4101 Addition of polycaprolactones tremendously improves the impact resistance of the coating Due to semicrystalline and low Tg segments Even more pronounced in a WB formulation

20 Weight force (g) Waterborne formulations Scratch resistance Scratch Plastic / fracture transition % 8% 13% Level of addition (wt-%) Capa 3050 Capa 4101 Both polycaprolactones lead to a better resistance towards permanent scratches up to 50% improvement with 4-functional Capa

21 Capa in 1K HMMM Formulations Set parameters Polyol Acrylic Capa Polyols Crosslinker (HMMM) Cymel 303* Varied parameters Acrylic polyol ref % Capa Polyols 0-30% Solvent Catalyst BuAc ptsa Mw of Capa polyols Branching of Capa polyols 2-3 Solid content 73% Polyol/melamine (solid) 80/20 H-value of Capa Polyols (mg KH/g) Curing 150 C, 10min * Cytec General properties Excellent appearance/compatility Good hardness Excellent chemical resistance A winning formula for performance

22 mm mm Capa in 1K HMMM Flexibility Erichsen flexibility Effect of increasing concentration of Capa Polyols Capa Polyols - wt% CAPA 2043 CAPA Erichsen flexibility Effect of M w of Capa Diols (20%) CAPA 2043 CAPA 2054 CAPA Capa Diols - M w (g/mol) Significant effect on flexibility due to flexible aliphatic chains Influenced by both amount and length of Capa A winning formula for performance

23 inchlbs Capa in 1K HMMM Impact resistance Impact resistance Effect of increasing concentration of Capa Polyol Capa Polyol - wt% CAPA 2043 CAPA 3091 Significant increase of impact resistance due to flexible aliphatic chains A winning formula for performance

24 Relative gloss recovery (%) Capa in 1K HMMM Self healing Gloss recovery Method: Scratching: 25 double rubs with scotch brite Recovery: C Gloss recovery - 20 Effect of increasing concentration of Capa Polyol Capa Polyol - wt% CAPA 2043 CAPA 3091 Significant improvement of gloss recovery Semicrystallinity, less internal stress and viscoelastic properties of cured coating A winning formula for performance

25 Technical benefits Conclusions Caprolactones are aliphatic, liquid, solvent free, low viscosity (polyester)polyols resin modifiers suitable as reactive diluents or reactive coalescing agents Properties of polycaprolactones in crosslinked coatings High gloss and good appearance Low viscosity low VC Excellent outdoor durability Excellent low temp flexibility and impact resistance Excellent abrasion resistance Excellent scratch resistance Possible self healing effect Due to semicrystalline, viscoelastic aliphatic structures with low Tg created by caprolactone segments Benefits can be obtained without compromising on chemical resistance and final hardness.

26 Final conclusions Polycaprolactones in 2K PUR Caprolactones are versatile tools to improve existing coating formulations Resin modifiers replace 5-20% acrylics or polyesters Easy to add Use to alter overall formulation properties Regarded as conventional raw materials but formulations should be balanced in order to take advantage of the unique properties from aliphatic structures with low Tg and relative high H-number Can be used in automotive coating, protective coatings (windmills), aerospace coatings, transportation coatings Many properties more pronounced in WB systems Caprolactones improve sustainability by prolonged life-time and reduced emissions Perstorp continues to develop new grades meeting customer needs Capa polyols can be very versatile tools (as resin modifiers) in a coating formulators toolbox

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