To look at acetals in a new light. Expanding Chemistry 8-9 November 2017

Transcription

1 To look at acetals in a new light Expanding Chemistry 8-9 November

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 Structure of the presentation Personal Care Methylal Butylal Cleaning /Degreasing Methylal Butylal Dioxolane TOU 7

8 Methylal Butylal PERSONAL CARE 8

9 9 INCI Names Acetals INCI Name Functions Methylal METHYLAL Solvent Butylal DIBUTOXYMETHANE Cleansing Emulsifying Solvent Source: CosIng - European Commission database 9

10 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: EC: REACH: INCI: Methylal Liquid 10

11 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

12 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: EC: REACH: INCI: Dibutoxymethane Liquid 12

13 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 % max. 13

14 General properties I. Excellent solvent II. Water miscible III. Low viscosity IV. Evaporation V. Low surface tension 14

15 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

16 I. Solvent power Silicone DM METHYLAL ETHANOL 16

17 I. Solvent power Sunflower oil METHYLAL ETHANOL 17

18 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

19 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

20 Example in the market Foot deodorant Anti-perspirant 47

21 UV filters solubility a a Solubility made until concentration limit b Source : BASF sunscreen simulator c Source : Annexe VI Regulation (CE) n 1223/

22 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

23 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

24 IV. Evaporation rate (BuAc=1) Methylene Chloride Diethyl Ether Acetone Methyl acetate Ethyl acetate IPA Ethanol Butyl acetate Butylal Methylal

25 Time (sec) Influence of the evaporation Drying time Influence of Methylal in water based body deo 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

26 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

27 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

28 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

29 V. Surface Tension mn/m Dichloromethane Butylal MEK Ethyl Acetate Acetone Butyl Acetate Ethanol IPA Methylal 29

30 Methylal Butylal Dioxolane TOU DEGREASING/ CLEANING 30

31 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

32 Methylal Butylal DEGREASING 32

33 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 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

34 Petroleum jelly degreasing Thin layer applied on the surface Dynamic immersion (stirring) 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

35 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

36 Silicone oil degreasing Static immersion 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

37 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

38 Methylal Butylal Dioxolane TOU CLEANING 38

39 39 Wetting of substrates NMP Dioxolane UP TOU Metal Polypropylene PVC- U

40 Polymers and Resins To remove residues in blenders, tanks, process lines, pumps or on tools: Dioxolane TOU for PU Epoxy Polyester Rosin (colophan) 40

41 Optical Cleaning Cleaner for optical devices with TOU Non labelled, not flammable High solvent power TOU used in ultrasonic tunnel machine NMP Substitution 41

42 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