To look at acetals in a new light Expanding Chemistry 8-9 November 2017 1
Acetals RANGE 2
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
Acetals CLP CLASSIFICATION & LABELLING 4
Classification Acetal Boiling point ( C) Flash Point ( C) CLP (pictogram) Methylal 42.3-30,5 Ethylal 87,1-7 Propylal 132,2 26 Butylal 177,9 62,2 None TOU 210 88 None 2-ethylhexylal 290 142 None 1,3-Dioxolane 76 <= 2,5 5
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
Structure of the presentation Personal Care Methylal Butylal Cleaning /Degreasing Methylal Butylal Dioxolane TOU 7
Methylal Butylal PERSONAL CARE 8
9 INCI Names Acetals INCI Name Functions Methylal METHYLAL Solvent Butylal DIBUTOXYMETHANE Cleansing Emulsifying Solvent Source: CosIng - European Commission database 9
Methylal Chemical Formula H H H C 3 H 8 O 2 H C O C O C H H H H CHEMICAL NAME: Dimethoxymethane CAS: 203-714-2 EC: 109-87-5 REACH: 01-2119664781-31 INCI: Methylal Liquid 10
Methylal CLP - Regulation (EC) No. 1272/2008 [CLP] Classification : Flammable liquids, Category 2 H225 Labelling : Highly flammable liquid and vapour, H225 Composition Product s Code 9900 / 9901 (deodorized) Pure grade Methylal 99.5 % min Methanol < 0.05 % Water < 0.5 % 11
Butylal CHEMICAL FORMULA: C 9 H 20 O 2 C 3 H 7 H 2 H 2 H 2 C O C O C C 3 H 7 CHEMICAL NAME: Dibutoxymethane CAS: 2568-90-3 EC: 219-909-0 REACH: 01-2119973500-41-0000 INCI: Dibutoxymethane Liquid 12
Butylal CLP - Regulation (EC) No. 1272/2008 [CLP] Classification : Not classified Labelling : No labelling applicable Composition Product s Code 1800 / 1801 (deodorized) Butylal Water 99.0 % min. 0.25 % max. 13
General properties I. Excellent solvent II. Water miscible III. Low viscosity IV. Evaporation V. Low surface tension 14
I. Solvent power Helps these ingredients to be Dissolved Polymers, UV filters organic, actives Dispersed UV filters, Talc, Silica Solubilized lipo-ingredients Silicones, Oils, Perfumes 15
I. Solvent power Silicone DM 500.000 METHYLAL ETHANOL 16
I. Solvent power Sunflower oil METHYLAL ETHANOL 17
Example in the market Hair car - Shining spray Ingredients Cyclomethicone (Cyclopentasiloxane), Methylal, Phenyl Trimethicone, Parfum (Fragrance), Linalool, Butylphenyl Methylpropional, Aqua (Water), Coumarin, Geraniol, Malachite (Malachite Extract), Parfum (Fragrance) 18
Example in the market Mousse against lice Es una espuma en spray a base de aceites naturales con propiedades para ahuyentar piojos y todo tipo de insectos. COMPOSICIÓN: Methylal, Isobutane, Propane, Alcohol Denat., Cyclopentasiloxane, Isodecane, Garapa Guaianensis Seed Oil, Cymbopogon Citratus Herb Oil, Aminopropylphenyl Trimetricone, Ethylhexyl Methoxycinnamate, Acetum, Quassia Amara Wood Extract, Prunus Armeniaca Fruit Extract, Polysorbate 80, Parfum, Butane, Citral, Iso Eugenol, Benzyl Salicylate, Geraniol, Hydroxyisohexyl 3-Cyclohexene Carboxaldehyde (Lyral), Butylphenyl Methylpropinal, Linalool, Citronellol, Hexyl Cinnamal, Limonene. 19
Example in the market Foot deodorant Anti-perspirant 47
UV filters solubility a a Solubility made until concentration limit b Source : BASF sunscreen simulator c Source : Annexe VI Regulation (CE) n 1223/2009 21
II. Water miscibility Acetals Solubility in water (g/l) Methylal 330 Butylal 0,225 to obtain full miscibility of acetal with water, a co-solvent needs to be added. Acetal % ethanol Methylal 9 Butylal 54 22
III. Viscosity Dynamic viscosity (at 25 C) Cp 2,50 2,00 1,50 0,98 1,00 0,50 0,32 0,00 23 * At 20 C
IV. Evaporation rate (BuAc=1) Methylene Chloride Diethyl Ether Acetone Methyl acetate Ethyl acetate IPA Ethanol Butyl acetate Butylal Methylal 24 0 2 4 6 8 10 12 14 16 18
Time (sec) Influence of the evaporation Drying time Influence of Methylal in water based body deo 300 250 200 150 100 50 0 Formulation A Water : 75 % Methylal : 18,6 % Sorbitol : 3 % Tween 20 : 3 % Germal 115 : 0.25 % Fragrance : 0.15 % Formulation B Water : 75 % Ethyl alcohol : 18,6 % Sorbitol : 3 % Tween 20 : 3 % Germall 115 : 0.25 % Fragrance : 0.15 % 25
Example in the market Hair Water Conditioning Ingredients Water, Trisiloxane, Alcohol Denat., Methylal, Panthenol, Glycerin, Benzophenone-4, Lactic Acid, Tocopheryl Acetate, Hydroxypropyltrimonium Hydrolyzed Corn Starch, Mentha Aquatica Extract, Rhodiola Rosea Root Extract, Malic Acid, Ceteartrimonium Chloride, Di-C12-15 Alkyl Dimonium Chloride, Citric Acid, Isopropyl Alcohol, PEG/PPG-14/4 Dimethicone, Ammonium Hydroxide, Polyquaternium-11, PCA, Tartaric Acid, Pyruvic Acid, Glycolic Acid, Phenoxyethanol, Fragrance, Limonene, Red 33 (CI 17200), Blue 1 (CI 42090) 26
Example in the market Lotion Ingredients Water (Aqua), Methylal, Glycerin, Qaternium- 26, Polysorbate-20, Sea Salt & Water (Dead Sea Water), Rose Centifolia Flower Water, Cucumis Sativus (Cucumber) Fruit Extract, Sodium Methylparaben, Imidazolidnyl Urea, Allantoin, Vaccinium Myrtillus (Bilberry) Extract, Saccharum Officinarum (Sugar Cane) Extract (and) Acer Sacchrium (Sugar Maple ) Extract (and)citrus Aurantium Dulcis (Orange)Fruit Extract (and) Citrus Medica Limonum (Lemon) Fruit Extract, Lactic Acid, Fragrance (Parfum), FD&C Blue#1(CI 42090), Butylphenyl Methylpropional, Linalool, Hydroxyisohexyl 3-Cyclohexene Carboxaldehyde, Hexyl Cinnamal, Dipentene 27
Example in the market Cooling spray Ingredients: METHYLAL, BUTANE, ALCOHOL DENAT.(SD ALCOHOL 3-C), CAPRYLIC/CAPRIC TRIGLYCERIDE, PARFUM (FRAGRANCE), CHAMOMILLA RECUTITA (MATRICARIA) FLOWER EXTRACT, TOCOPHEROL 28
V. Surface Tension mn/m 28 27 26 25 24 23 22 Dichloromethane Butylal MEK Ethyl Acetate Acetone Butyl Acetate Ethanol IPA 21 20 Methylal 29
Methylal Butylal Dioxolane TOU DEGREASING/ CLEANING 30
Which acetal at a glance Methylal Butylal Dioxolane TOU Solvent power High Good High high Water miscibility Partial None Total Total Evaporation Extremely fast Slow Fast Very slow Polarity Low Very low High High Surface tension Very low Low Medium Medium What for Mainly under spray form: - Cleaning - Degreasing - Degreasing - Cleaning (rubber, sealant, bitumen..) - Cleaning (fast evaporation ) - Cleaning (not hazardous ) 31
Methylal Butylal DEGREASING 32
Degreasing Grease/lubricant applied in excess on the surface of the substrate Part of the substrate is dipped into a beaker filled with Butylal: Static or dynamic conditions (stirring) Room temperature 10-15 or 30 minutes Dipped part air-dried only, no paper/cloth wiping Comparison before/after dipping: Aspect/appearance of the treated part of the substrate Water droplet test: Higher angle of contact (bead shape): surface more hydrophobic Lower angle of contact (flat shape): surface more hydrophilic 33
Petroleum jelly degreasing Thin layer applied on the surface Dynamic immersion (stirring) 10-15 minutes Room temperature Before dipping Water droplet contact angle > 90 More hydrophobic surface After dipping Water droplet contact angle < 90 More hydrophilic surface Non immersed part Immersed part 34
Lithium/calcium grease degreasing Static immersion 30 minutes Room temperature Non immersed part Immersed part Water droplet contact angle > 90 Surface more hydrophobic Water droplet contact angle < 90 Surface more hydrophilic 35
Silicone oil degreasing Static immersion 10-15 minutes Room temperature Non immersed part Immersed part Water droplet contact angle > 90 Surface more hydrophobic Water droplet contact angle < 90 Surface more hydrophilic 36
Degreasing Butylal is an efficient degreaser: Can solubilize different types of grease/lubricant Thin or thick layer Static or dynamic conditions At room temperature Time efficiency 37
Methylal Butylal Dioxolane TOU CLEANING 38
39 Wetting of substrates NMP Dioxolane UP TOU Metal Polypropylene PVC- U
Polymers and Resins To remove residues in blenders, tanks, process lines, pumps or on tools: Dioxolane TOU for PU Epoxy Polyester Rosin (colophan) 40
Optical Cleaning Cleaner for optical devices with TOU Non labelled, not flammable High solvent power TOU used in ultrasonic tunnel machine NMP Substitution 41
Modeling/hobby paint cleaning TOU to dissolve wet or dried acrylic, enamel and cellulose paints from brushes Can dissolve uncured epoxy and polyester resins as well Tested on all types of brush: sable, nylon, etc Works on airbrushes with Teflon or O-ring seals 42