Cognis EP Surfactants. Matthew Guo / June 1st, 2011 Functional Products

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1 Cognis EP Surfactants Matthew Guo / June 1st, 2011 Functional Products

2 Content EP-Surfactants Product Range Some basic Surfactants Emulsion Polymerization Application Tests Some Concepts in EP Disponil NG Series Backup slides 2 Cognis is now part of BASF

3 EP-Surfactants Product Range Overview Portfolio Range 3 Cognis is now part of BASF

4 EP Surfactants - Basic Definitions Surfactants are a critical component of a waterborne polymer latex. They control the size of the polymer particle during production and ensure latex stability during and after processing 4 Cognis is now part of BASF

5 Surfactant - Characteristics The hydrophobe / hydrophilic balance in a surfactant molecule is responsible for the incorporation between oil and aqueous phases to remove barriers between regularly non-miscible substances. 5 Cognis is now part of BASF

6 Surfactant - Characteristics 6 Cognis is now part of BASF

7 Surfactant - Characteristics 7 Cognis is now part of BASF

8 Product Manufacture / Oleo chemistry 8 Cognis is now part of BASF

9 Product Manufacture Oleo chemistry 9 Cognis is now part of BASF

10 Refinement Technolgies in EP Surfactant Manufacture 10 Cognis is now part of BASF

11 Products and Solutions 11 Cognis is now part of BASF

12 Cognis EP Surfactant Portfolio by Chemistry 12 Cognis is now part of BASF

13 Recommendation Guideline EP- Surfactants 13 Cognis is now part of BASF

14 Recommendation Guideline EP- Surfactants 14 Cognis is now part of BASF

15 Some basic Surfactants 15 Cognis is now part of BASF

16 Fatty Alcohol Ethoxylates OH EO O O H n Reaction Refining Fatty Alcohol EO M M Ethoxylate 16 Cognis is now part of BASF

17 Fatty Alcohol Ethoxylates HLB Value (Hydrophile-lipophile balance) HLB value can be calculated roughly from their structural group (Griffin, 1954). HLB Value = 20 X MW H MW H + MW L For example, in the case of Lauryl alcohol 7EO. CH 3 (CH 2 ) 10 CH 2 (OCH 2 CH 2 ) 7 OH MW H HLB Value = 20 X MW H + MW L 339 = 20 X = Cognis is now part of BASF

18 Fatty Alcohol Ethoxylates Product Properties Eumulgin O 2 Eumulgin O 5 Eumulgin O 10 Eumulgin ET 5 Eumulgin ET 10 Chemical description HD-Ocenol 50/55 V + 2 EO HD-Ocenol 50/55 V + 5 EO HD-Ocenol 50/55 V + 10 EO HD-Ocenol 50/55 III V + 5 EO HD-Ocenol 50/55 III V + 10 EO Appearance clear to cloudy liquid clear to cloudy liquid pasty cloudy liquid pasty Colour yellowish yellowish yellowish yellowish yellowish Active substance [%] Water content [%] < 0.3 <= 0.5 < 1.0 <= 0.5 <= 0.5 Hydroxyl value [kg KOH/g] Turbidity Temp. [ C] (10% in BDG) Cloud point [ C] Solidification point [ C] < <= 30 < 30 ph value (1%) Registration AICS/DSL/ ENCS/EU/INV/ KECI/PICCS/ TSCA According to EU- Detergent Regulation yes Biodegration readily biodegradable 18 Cognis is now part of BASF

19 Fatty Alcohol EO/PO Adducts CH 3 Principle Structure: CH 3 (CH 2 ) n CH 2 (OCH 2 CH 2 ) x (OCHCH 2 ) y OH Dehypon LS 24 / LS 36 / LS 45 / LS 54 / LS 64 Performance Profile low foaming at higher temperatures sufficient antifoam capability stable at acidic and moderate alkaline ph 19 Cognis is now part of BASF

20 Fatty Alcohol EO/PO Adducts Product Properties Method Dehypon LS 24 Dehypon LS 36 Dehypon LS 45 Dehypon LS 54 Dehypon LS 64 Chemical description FA C12/14+2E O+4PO FA C12/14+3E O+6PO FA C12/14+4E O+5PO FA C12/14+5E O+4PO FA C12/14+6E O+4PO Physical Form liquid liquid liquid liquid liquid Colour yellowish yellowish yellowish colourless colourless Active substance [%] Water content [%] DGF C-III 13a <0.5 <0.5 <0.5 <0.5 <0.5 Hydroxyl value [kg KOH/g] DGF C-V 17a/ Q-C Cloud Point H2O, 1% [ C] DIN Cloud Point in BDG [ C] approx. 28 approx. 35 approx. 43 Turbidity Titration Value [ml] approx. 18 approx. 21 approx. 26 Density [g/cm³, 70 C] DIN Storage <40 C, 2 years 20 Cognis is now part of BASF

21 Fatty Alcohol EO/PO Adducts Defoaming Dehypon LS 24 Dehypon LS 36 Dehypon LS 45 Dehypon LS 54 Dehypon LS 64 Hydrophilie/Cleaning 21 Cognis is now part of BASF

22 Manufacturing APG surfactants coconut, palm Cognis is a world leader in APG production corn, potato, wheat coconut oil trans-esterification hydrogenation distillation fatty alcohol starch hydrolysis glucose 22 Cognis is now part of BASF

23 The Sulphation Process Technologies OH SO 3 CSA OSO 3 H Y O 3 SO 23 Cognis is now part of BASF

24 Emulsion Polymerization 24 Cognis is now part of BASF

25 Emulsion Polymers where are they to be found? Typical Applications 25 Cognis is now part of BASF

26 Emulsion Polymerization : polymerization equipment in the laboratory 26 Cognis is now part of BASF

27 Emulsion Polymerization A typical latex formulation consists of: Monomers Initiator Buffer Water Emulsifier Water: Water is the continuous phase, so required for emulsification and as heat transfer medium. Polymerization behavior is strongly influenced by water quality. Preferred is the use of emineralized water. High inorganic salt content, e.g. in tap water, can inhibit the polymer reaction and will cause coagulation. 27 Cognis is now part of BASF

28 Emulsion Polymerization Monomers 28 Cognis is now part of BASF

29 Emulsion Polymerization Monomers 29 Cognis is now part of BASF

30 Emulsion Polymerization Monomers the reactive C=C double bond: 30 Cognis is now part of BASF

31 Emulsion Polymerization Initiators: Oxidation catalysts ammonium persulfate potassium persulfate sodium persulfate Redox catalysts persulfates / sulfoxides (hydrogensulfite, thiosulfate) / metal salts Organic catalysts*) tertiary butyl- and cumene hydroperoxide *) organic initiators are used as secondary catalysts to increase the conversion rate 31 Cognis is now part of BASF

32 Emulsion Polymerization Buffers: bi-carbonate NaHCO3 borax Na2B4O7. 10 H2O soda Na2CO3 sodium dihydrogenphosphate NaH2PO4. H2O The ph value during polymerization is primarily in between ph 2 and 9. Monomers as vinyl acetate show the tendency to hydrolysis at lower ph-values. To prevent hydrolysis, use of buffers is recommended. 32 Cognis is now part of BASF

33 Emulsion Polymerization 33 Cognis is now part of BASF

34 Emulsion Polymerization all acrylic formulation: the reactor charge is given into the reactor, preemulsion is prepared by filling the water phase into the preemulsion flask and adding the monomers under stirring the apparatus is flushed w/ nitrogen for at least 15 minutes the heating jacket is adjusted to approx. 93 C, mea nwhil e 20ml of the preemulsion are added to the reactor 2 minutes after the polymerization start has been observed, the continuous dosage of the preemulsion is started and has to be finished in 80, +/- 5 minutes postpolymerization is placed for 1 hour, heating jacket temperature is adjusted to 96 C while the post polymerization t akes p lace the emulsion is cooled to < 40 C and the neutraliza tion c harge is added filter the emulsion through a 80 µm sieve 34 Cognis is now part of BASF

35 Emulsion Polymerization Reaction mechanism what s happening in the reactor? 35 Cognis is now part of BASF

36 Emulsion Polymerization 36 Cognis is now part of BASF

37 Emulsion Polymerization the different phases of the polymerization process: 37 Cognis is now part of BASF

38 Emulsion Polymerization 38 Cognis is now part of BASF

39 Emulsion Polymerization small dosage big effect! 39 Cognis is now part of BASF

40 40 Cognis is now part of BASF Application Tests

41 Determination of the viscosity 41 Cognis is now part of BASF

42 Determination of the solid content 42 Cognis is now part of BASF

43 Determination of the particle size 43 Cognis is now part of BASF

44 Determination of the electrolyte stability 44 Cognis is now part of BASF

45 Emulsion Polymerization 45 Cognis is now part of BASF

46 Emulsion Polymerization 46 Cognis is now part of BASF

47 Emulsion Polymerization 47 Cognis is now part of BASF

48 Emulsion Polymerization 48 Cognis is now part of BASF

49 Determination of the shear stability 49 Cognis is now part of BASF

50 Determination of the foaming behavior purpose of the method: Through this method a statement on foam properties of polymerdispersions and aqueous emulsifier solutions and the defoamer efficiency to this kind of systems can be given. application: Aqueous and solvent based, filmbuilding latices for adhesive-, paint-, textileand coating applications. Application range Foam behavior at temperatures between 10 to 90 C description: 50g of the latex will be diluted in 450g deionised water and quantitative charged into the foam apparatus. The foam apparatus is designed as graduated cylinder with double layer for thermostating and a flow inducer. Usual the mesurement will execute at 20 C. (For emul sif ier testing 1% surfactant (active substance) in 500 g aq. solution is used.) The thermostated dispersion is pumped in circulation for 10 min., with a flow of 3 l/min.! The dispersion or test liquid is taken from the bottom of the cylinder and re-filled at the 2000ml mark. During this procedure foam formation takes place. After foam formation to a maximum volume, the flow inducer is stopped and the foam decomposition will be messured as ml foam volume after 1, 2, 3, 5, 10, 15, 20 and 30min! Only for dispersions! After 30 min. the dispersion will be foamed for another 5 min. to the maximum volume and then 0,1 % (or less) defoamer are added on the foam surface. Here the foam formation will be measured after 10 min., when the defoamer has been added to the polymer dispersion. result: The result will be summarized in a diagramm. The diagramm shows the max. of foam volume versus time. The result of the defoamer test will be evaluated 50 Cognis is now part of BASF

51 Determination of the freeze / thaw stability purpose of the method: This method describes the determination of the freeze-thaw stability of polymer dispersions. application: Aqueous and solvent based, film building latices for adhesive-, paint-, textile- and coating applications. description: 50g of the dispersion will be filled in a 75ml closeable bottle. The bottle will be placed in a thermostated room and cooled down to 5 C within 16h. Subsequently it is warmed to 23 C within 8 h again. When the 23 C are reached, the dispersion is checked about its stability (1 cycle). Is it stable the cycle will be repeated until it is instable, but for max. 4 times again. (five cycles at all) Dispersions which are stable after the five cycles will be replaced by a new sample wich is cooled the same way for five cycles again, but this time to a temperature which is 5 C below the minimum temperature during the last cycles, but at most until 25 C. result: The result is the number of cycles, at which the dispersion becomes instable. Note the temperature next to the value. literature: ISO Cognis is now part of BASF

52 Determination of the water absorption purpose of the method: This method describes the determination of the water absorption of polymer films. application: Aqueous and solvent based, film building latices for adhesive-, paint-, textile-, and coating applications. description: For the determination of the water absorption three films of each dispersion (shape 75 * 35 * 0,5 mm) will be tested. Those films can be prepared in especially designed PTFE-forms and dried for 48h at 50 C. The dried films will be taken out of the form and its weight will be measured on a scale (precision: 0,1 mg). Then the films will be placed in deionised water at room temperature for 24, 48 or x hours. After that the weight of the wet film will be measured. First the film will be slightly touched with a tissue to remove water droplets from the film surface result: As result the mass of the absorbed water in relation to the mass of the dry film is calculated in percent. It is calculated on the mean value of the three films. The single values have to be within 0,5 % deviation. %W = percent water absorption mn = mass wet film mt = mass dry film literature: DIN EN Cognis is now part of BASF

53 Determination of the water / alkali resistance 53 Cognis is now part of BASF

54 Some Concepts in EP Emulsification Surfactants and foam Gelling phase Critical micelle concentration 54 Cognis is now part of BASF

55 Emulsification Surfactant structure of different anionics. 55 Cognis is now part of BASF

56 Emulsification 56 Cognis is now part of BASF

57 Surfactant and foam Foams are colloidal systems in which the dispersed phase is a gas and the continuous phase is a liquid. The foam bubbles are made possible by the presence of surfactants at the gas-liquid interface area, but they are thermodynamically instable due their interfacial free energy. However, some foams can persist for a long time in the absence of external disturbance, while others break down rapidly, this depending on the stability of the liquid film formed. 57 Cognis is now part of BASF

58 Surfactant and foam Foam in EP occurs in various positions. mostly during removal of not reacted monomer Stripping process or during filling the tank. Foam measurement: pictures of a new nonionic with good foam decay Foam creation under repetitious, measureable conditions by using SITA Foam Tester 58 Cognis is now part of BASF

59 Surfactant and foam Foam measurement: pictures of a new nonionic with good foam decay 59 Cognis is now part of BASF

60 Surfactant and foam 60 Cognis is now part of BASF

61 Gelling phase Nothing is better than a convenient handling of surfactant in special if the customers dilute his raw materials for his emulsion polymerization process. 61 Cognis is now part of BASF

62 Gelling Phase Below is a typical phase diagramm for surfactant, as a function of concentration (in water) and Temperature. 62 Cognis is now part of BASF

63 Micelle Size and Viscosity At higher concentration, surfactant can also form elongated columns that pack into hexagonal Arrays. The columns are separated form one another by water. At this point the viscosity is high. Or in other words gelling occurs. 63 Cognis is now part of BASF

64 Gelling Phase Phase diagram, this gives information about the solubility of the surfactant with water. Surfactants are liquid below 30% actice or >/= 70-80% active. Between a gel phase or Liquid-crystalline phase occurs. The new nonionic avoid those gel phases. 64 Cognis is now part of BASF

65 Critical micelle concentration, cmc 65 Cognis is now part of BASF

66 Critical micelle concentration, cmc 66 Cognis is now part of BASF

67 Critical micelle concentration, cmc Inside of a micelle the polymerization takes place. The micelles are also called mini reactors. Due to low concentration of surfactant the shape of the micelle is more or less spherical. During the polymerization the micelle swells. The amount is an important key factor! To run an EP you need surfactant To run a stable EP you need enough surfactant, that means >/= cmc value To achieve a long term stable Polymer disperion (latex) during storage time and a stable latex during handling like mixing the latex into an paint-emulsion, the performance of the used surfactant should be sufficient. BUT the amount and kind of surfactant affects: particle size; polymer film properties; application performance and very important: process stability of customers EP system 67 Cognis is now part of BASF

68 Disponil NG Series The new generation of gel-free non-ionic surfactants 68 Cognis is now part of BASF

69 Benefits of Disponil NG Series Sustainability Aspects APEO-free FDA approved Derived from renewable raw materials Energy saving through easier and faster handling Performance Highlights Excellent phase behavior No Gel Fast foam decay in the surfactant solution and in the polymerization process Low pour point High and constant quality Low coagulum and high mechanical stability in the final latex 69 Cognis is now part of BASF

70 Disponil NG Series Disponil NG Surfactants are modified ethoxylated C12/C14 fatty alcohols 70 Cognis is now part of BASF

71 Disponil NG Series - Test Results Disponil NG Series shows outstanding results in the following parameters: Excellent Phase Behaviour When diluted with water, Disponil NG presents no gel phases over the whole concentration range Low Foaming Fast decay of foam in both, the surfactant solution and the polymer latex Low Pour Points Disponil NG 3050 LP shows an extremely low pour point below -15 C 71 Cognis is now part of BASF

72 Disponil NG Series Test Method Phase Behaviour 1. The Active matter material in Disponil NG Surfactants was diluted with water to obtain samples with various concentrations 2. Each sample was placed in a temperature bath until thermal equilibrium was attained 3. Temperature was lowered stepwise by 1 C until the sample solidified 72 Cognis is now part of BASF

73 Disponil NG Series Phase Behaviour Disponil NG presents no gel phases over the whole concentration range Temperature C Disponil NG 3070 Standard surfactant iso-tridecyl-oh 30EO Active Substance % 73 Cognis is now part of BASF

74 Disponil NG Series Phase Behaviour Disponil NG presents no gel phases over the whole concentration range Temperature C 10 0 Disponil NG 1080 Disponil NG 2080 Disponil NG 3070 Disponil NG Active Substance % 74 Cognis is now part of BASF

75 Disponil NG Series Test Method Foam Behaviour 1. Disponil NG Surfactants were diluted with demineralized water containing NaCl (1 % Active matter, 0.05 % NaCl) 2. Surfactant solutions were examined in a SITA Foam Tester ("R-2000") at: Temperature T = 20 C Stirring Speed Stirring Interval Measurement Measurement Interval R = 1100 r.p.m. τ = 3 x 10 sec t = 20 min θ = 10 sec 3. Determination of height of foam column by measurement of electrical conductivity 75 Cognis is now part of BASF

76 Disponil NG Series Foam Behaviour Disponil NG show fast decay of foam in both, the surfactant solution and the polymer latex 400 1% surfactant solution Foam Column [mm] Disponil NG 1080 Disponil NG 2080 Disponil NG 3070 Disponil NG 4060 iso-tridecyl-oh 30EO :00 02:24 04:48 07:12 09:36 12:00 14:24 16:48 19:12 21:36 Time [min:sec] 76 Cognis is now part of BASF

77 Disponil NG Series Pour Point Disponil NG 3050 LP* offers easy handling through its extremely low pour point Product name Active Matter Pour Point Disponil NG 3050 LP* 50% <-15 C Iso-C13 alcohol 70% 5 C *Low pour point 77 Cognis is now part of BASF

78 Disponil NG Series Registration EINECS (EU), EINCS (Japan), TSCA (USA), DSL (Canada), KECI/ECL (Korea), IECSC (China), PICCS (Philippines), AICS (Australia), NZIoC (New Zealand) FDA 21 CFR , , , Cognis is now part of BASF

79 Top Performance of Disponil NG Series Key characteristics Excellent phase behaviour No Gel Fast foam decay in the surfactant solution and in the polymerization process Low pour point Low foaming performance in final applications FDA approved suitable for all types of latexes as in-process non-ionic surfactant as post-stabilization surfactant 79 Cognis is now part of BASF

80

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