Acetals, more than solvents. Expanding Chemistry 8-9 November 2017

Transcription

1 Acetals, more than solvents Expanding Chemistry 8-9 November 2017

2 Acetals RANGE 2

3 Acetals Name Methylal Formula CH3-O-CH2-O-CH3 Ethylal CH3-CH2-O-CH2-O-CH2-CH3 Propylal CH3-CH2-CH2-O-CH2-O-CH2-CH2-CH3 Butylal CH3-CH2-CH2-CH2-O-CH2-O-CH2-CH2-CH2-CH3 TOU CH3-O-CH2-CH2-O-CH2-O-CH2-CH2-O-CH3 2-ethylhexylal n Bu -CH -CH 2 -O-CH 2 -O-CH 2 -CH- n Bu Et Et Dioxolane 3

4 Acetals CLP CLASSIFICATION & LABELLING 4

5 Classification Acetal Boiling point ( C) Flash Point ( C) CLP (pictogram) Methylal ,5 Ethylal 87,1-7 Propylal 132,2 26 Butylal 177,9 62,2 None TOU None 2-ethylhexylal None 1,3-Dioxolane 76 <= 2,5 5

6 General Characteristics Low Toxicity No pictogram Low Eco-Toxicity No pictogram Safe for human health and environment VOC 2-ethylhexylal is not a VOC according to the European general VOC definition. Bio-sourced Acetals or potentially Ethylal (> 85%) 6

7 Acetals PROPERTIES 7

8 General Properties I. Solvent power II. Water miscibility III. High to low evaporation rate IV. Medium to low surface tension V. Medium to low viscosity 8

9 I. Solvent Power 9

10 I. Solvent power Kauri -Butanol

11 II. Water Miscibility 11

12 Water miscibility II. Water Miscibility 12

13 III. Evaporation 13

14 Evaporation rate (BuAc=1) Methylene Chloride Diethyl Ether Acetone Methyl acetate MEK Ethyl acetate DMC IPA Ethanol Perchlo Toluene Xylene 1-Methoxy-2-propanol (PM) DMSO NMP Butyl acetate 2-Ethylhexylal TOU Butylal Propylal Dioxolane Ethylal Methylal

15 IV. Surface Tension 15

16 IV. Surface Tension Low mn/m 34 1,3-Dioxolane 32 TOU Butylal Ethylal Methylal Propylal Toluene 2-Ethylhexylal DPM PM Methylene chloride Ethyl Acetate Butyl Acetate Methyl acetate Methyl MEK acetate Butyl Acetate Acetone Ethanol 16

17 IV. High mn/m Surface Tension Propylene carbonate DMSO NMP Benzyl alcohol 34 1,3-Dioxolane DBE DMF TOU Ethylhexylal THF Toluene DPM PM 17

18 V. Viscosity 18

19 V. Viscosity Kinematic Acetal Kinematic viscosity (mm2/s) 25 C Methylal 0,371 Ethylal 0,507 Propylal 0,77 Butylal 1,18 TOU 1,532 2-Ethylhexylal 9,42 1,3-Dioxolane 0,553 19

20 Methylal Acetone * Methyl acetate* Ethylal MEK* Methylene Ethyl Acetate* 1,3-Dioxolane Toluene* DMC Propylal Butyl Acetate* DMF Butylal Ethanol TOU NMP 1-methoxy-2- DMSO* IPA* Benzyl alcohol 2-Ethylhexylal V. Viscosity Dynamic viscosity (at 25 C) 8,00 7,00 6,00 5,00 4,00 Cp 7,98 3,00 2,00 1,00 0,32 0,42 0,58 0,64 0,98 1,51 0,00 20 * At 20 C

21 Example to illustrate the solvent power SOLUBILITY OF RESINS

22 Heat resistant/ protective coatings Typically involve silicone resins: in liquid form (dispersed in toluene or xylene) as flakes Flakes solubility: in aromatic and chlorinated solvents in selected ketones, acetates and esters Flammability and/or labelling issues Boiling point ( C) Flash point ( C) Evaporation rate (BuAc = 1) Viscosity (mpa.s) CLP Labeling Toluene Xylene IPA MEK Ethyl acetate Dichloromethane Methylal 42.3 < TOU

23 Heat resistant/ protective coatings TOU as safe alternative Aerosol/spray applications: Methylal Flake silicone resin (RSN -0217) MW All Phenyl substituted Silanol content : 6% Silicon dioxide content: 47% Flake silicone resin (RSN-255) MW Phenyl : 1 Methyl Silanol content : 5% Silicon dioxide content: 51% 50% in Toluene 50% in TOU 50% in Methylal 60% in TOU 50% in Toluene 50% in Methylal 50% in TOU 23

24 Resins / Polymers Maximum Solubility in Lambiotte s Acetals a,b,c Coatings (Paint, Ink)

25 Resins / Polymers Maximum Solubility in Lambiotte s Acetals a,b Adhesive

26 Example to illustrate the surface tension WETTING OF SURFACE

27 Wetting of substrates Water 30% Methylal in water 5% Ethylal in water Polypropylene Teflon PVC-U 27

28 Wetting of substrates NMP Dioxolane UP TOU Metal Polypropylene PVC-U 28

29 Acetals for Coatings 29

30 Coatings Non-stick coatings Dioxolane in the solubilization of acrylates and vinyl ester resin Dioxolane or TOU as aprotic polar solvents in the formulation of polyimide and/or polyamide-imide resins coatings UV-curing Coatings and Adhesives TOU Miscible with both water and solvent-borne systems No/limited label TOU used as reactive diluent (10%) To improve the adhesion of acrylate-based UV-cured adhesive on PMMA substrate 30

31 Acetals for Inks Pigments/dyes solubility 31

32 Solubility/Bleed of pigments 20 g solvent 0,5 g pigment Type: dyed/pigmented melamine, sulphonamide, formaldehyde thermoplastic copolymer Trade name: FIESTA A Thermoplastic general purpose grade offering excellent brightness and colour strength for use in printing ink, paint and paper coatings systems containing water or mild solvents. The particle size ensures that good dispersion can be achieved with high -speed stirrers. Colour: Magenta 10 Solubility Bleed Acetone Soluble TOU Soluble Toluene None Methylal None

33 Solubility/Bleed of pigments 20 g solvent 0,5 g pigment Type: dyed/pigmented melamine, sulphonamide, formaldehyde thermoplastic copolymer Trade name: FIESTA FTX This ultra high-strength series is chemically similar to T series but has a finer particle size and is up to 50% stronger, making it suitable for thin film solvent based applications such as gravure and screen printing inks. Colour: Flame orange 4 Solubility Bleed Acetone Soluble TOU Soluble Toluene Slight Methylal Slight

34 Ink jet printing Ethylal Sustainability (bio-sourced) Boiling point its boiling point is 88 C., which is close to the boiling points of ethanol (78 C) and MEK (80 C), although higher Vapor pressure its vapor pressure at 25 C. is 80 mbar which is very close to that of ethanol which is 76 mbar Evaporation rate the evaporation rate is greater than that of similar compositions based on ethanol alone, while this evaporation rate is closer to that of MEK, whereas the boiling point of ethylal is 8 C higher than that of ethanol Solvent Power resins (polyhydroxystyrene, phenolic resins, acrylic acid resins, rosin and some of its derivatives, ketone and aldehyde resins), dyes - Ethanol, MEK, Acetates, Acetone EX: Inkjet printing (for continuous deflected jet printing)

35 Acetals for Adhesive & Bonding 35

36 Which ones Dioxolane Excellent solvent Listed in Commission Regulation n 10/2011 on plastic materials and articles intended to come into contact with food Methylal Good solvent Fast evaporation Methylal appears on the Combined Positive List Of Organic Substances in Contact with Drinking Water of the 4MS Group common use substances that appear on the existing Positive Lists in use in France, Germany, United Kingdom and the Netherlands Butylal Not hazardous Good solvent Slow evaporation Butylal appears on the Combined Positive List Of Organic Substances in Contact with Drinking Water of the 4MS Group common use substances that appear on the existing Positive Lists in use in France, Germany, United Kingdom and the Netherlands 36

37 37 ADHESIVES Known qualifications PVC adhesives PU adhesives PC bonding Heat sealable adhesives Sleeves Contact glues Glue Remover

38 Dioxolane substitutes: THF H225: Highly flammable liquid and vapour. H319: Causes serious eye irritation. H335: May cause respiratory irritation. PolyVinylChloride (adhesive/glue/cement) H351: Suspected of causing cancer <state route of exposure if it is conclusively proven that no other routs of exposure cause the hazard>. Concentration range (%)>= 25.0 : Eye Irrit. 2 / H 319 and STOT SE3 / H335 Formula usually containing also Cyclohexanone MEK example : PVC glues for pipes - tubes 38

39 Compatibiliyof PVC with the Acetals % Weight change Polyvinyl Chloride (PVC) Solvin 257RF (Solvay) Methylal Ethylal Propylal Butylal 1,3 - Dioxolane Glycerol Formal 2- Ethylhexylal 44,08 0,555 0,0923 0,0054 D 0,133 0,198 D TOU D = Destructuration Dioxolane and TOU are good components for PVC adhesives 39

40 Dioxolane substitute of: 1,4 - Dioxane DMF PU adhesives example : PU glues for packaging 2-Ethylhexylal substitute of: Toluene Xylene example : Non VOC PU glues for parquet/automotive industry 40

41 PC adhesive bonding Dioxolane to substitute: Methylene chloride for solvent bonding example : brands Makrolon Sustanat TECANAT Makrolon for medical devices Example : medical equipment, aeronautic seats Polycarbonate parts to be bonded : contact surfaces are slightly dissolved with solvent and then pressed together 41

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43 43 Flexible packaging adhesives Dioxolane is used in sealable adhesives : example : microwave and dairy food packaging 43

44 Sleeves Dioxolane to substitute: THF in PVC sleeves MeCl in PET or APET sleeves example : shrink sleeves 44