Tecnoflon FKM and FFKM portfolio: an overview on standard grades and specialties

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1 Tecnoflon FKM and FFKM portfolio: an overview on standard grades and specialties R. Villa Utrecht,

2 Introduction

3 History of FKM-FFKM 1892: Development of fluroalkanes (Swarts reaction) 1955: Elastomeric copolymer VDF-CTFE (M.W. Kellogg Co.-US Army) 1956: Copolymer VDF-HFP (Dupont) improved heat stability 1960: Terpolymer VDF-HFP-TFE (Dupont) better chemical resistance 1960s: Perfluoroelastomers - copolymers TFE/PMVE (Dupont) 1960s: Copolymers TFE-P (Dupont, Asahi Glass) 1960: Copo and terpolymers using 1HPFP instead of HFP (Montecatini-Edison SpA) 1970: Bisphenol curing chemistry (Dupont and 3M) 1970s: Terpolymers VDF/TFE/PMVE improved low T performance Late 1970s: Peroxide curing chemistry Br as CSM (Dupont) I as CSM (Daikin)

4 Solvay Solexis: FKM and FFKM portfolio

5 Presentation overview Tecnoflon Solvay Solexis tradename for Fluoroelastomers (FKM) and perfluoroelastomers (FFKM) 1. Introduction Fluoroelastomers key benefits 2. Fluoroelastomers classification/performances 3. Tecnoflon grades portfolio: fluoroelastomers 4. Perfluoroelastomers classification/performances 5. Tecnoflon PFR grades portfolio: perfluoroelastomers

6 Fluorine plus Typical properties of fluoroelastomers are: Excellent chemical resistance Excellent thermal resistance Very low permeability Very good weather, O 2 and O 3 resistance + Fluorine

7 Fluorine plus ASTM D2000/SAE J200 Spec. System EA ACM CSM CR FFKM ECO NBR FKM FVMQ Heat Resistance ( C) FKM and FFKM are at the top of the range! Swelling in IRM 903 oil (%)

8 Fluoroelastomers applications Automotive industry Aerospace industry Chemical & Processing industry Oil field / Mining Semicon industry

9 Fluoroelastomers classification FKMs are classified according to monomer composition and ratio FKMs are manufactured by polymerization of a limited number of monomers: Vinylidene Fluoride (VF 2 ) CH 2 =CF 2 Hexafluoropropylene (HFP) CF 2 =CF-CF 3 Tetrafluoroethylene (TFE) CF 2 =CF 2 Perfluoroalkylvinylether (PAVE) CF 2 =CF-OCF 3 (main monomer MVE when Rf = CF3) Ethylene (E) CH 2 =CH 2 Propylene (P) CH 2 =CH-CH 3 FKMs can be further differentiated by curing chemistry Two main cure systems: Bisphenol Peroxide

10 Chemical composition Fluoroelastomers (FKM) are classified according to monomer composition (ASTM D1418): Type 1 VF 2, HFP (Bisphenol) Example: Tecnoflon FOR 80HS Type 2 VF 2, HFP, TFE (Bisphenol or Peroxide)» Example: Tecnoflon FOR 4391 (Bisphenol)» Example: Tecnoflon P 959 (Peroxide) Type 3 VF 2, TFE, PMVE (Bisphenol or Peroxide)» Example: Tecnoflon PL 855 (Peroxide) Type 4 TFE, P, VF 2 (Bisphenol) Type 5 TFE, HFP, VF 2, E, PMVE (Peroxide)» Example: Tecnoflon BR 9151 (Peroxide) Perfluoroelastomers (FFKM) are usually TFE / PAVE (MVE) copolymers

11 ! "# CF 3 ( PR 4 ) + - O O - ( PR 4 ) + CF 3 $# O=C CH 2 -CH=CH 2 N C=O CH 2 =CH-CH 2 -N C O N-CH 2 -CH=CH 2

12 &* &'()&#"%!$# ) " &" * +)",-../- '&&() %!#"!!# ),!" +" *" #" -.!"" * & %&

13 Tecnoflon Bisphenol Curable A full range of products for all kinds of items and processing technologies (compression, injection, transfer, extrusion) Tailor made materials for special requirements New copolymers with improved performances (HS grades manufactured in US plant) For bisphenol curable FKM, Solvay Solexis supplies: Raw gum Cure incorporated materials (rubber + bisphenol + accelerator + possibly processing aids) Cure incorporated materials for rubber-metal bonding

14 Tecnoflon Bisphenol Curable Portfolio 7 6. # &0 11 /01/20/'" ("230 /4"23 56#"&230 01/#" )&0 123, #+(04+( 56#+(& 56'+'0 '+'0'+'78 /6) 1-#-11 56#+'& 8'+'08'+'8 4 )",5 & 56'" 0 &$ 56#+&! 0 56$+(" 0 &+7$ 564+(# &4!&

15 Tecnoflon Peroxide Curable A full range of products both for compression and injection moulding (high low Mooney viscosity) Very fast curing rate Excellent mechanical properties Very low compression set Very low post-curing times (1 2 h) Excellent processability For Peroxide curable FKM, Solvay Solexis supplies: Raw gum

16 Tecnoflon Peroxide Curable Portfolio )",5 8 )&0 /6) <0/6) 13 "93 -*#$0-$#$ &# 3, "9$ -*#40-4#4 $ 1: "92-8*##0-8(## +" 11 "91-8##$!4 11 "9$ -8*#(0-4#(!* 1192 "9,- 9-8(#$+":9-8*#$+" +" 1-9" "9;- 9-8*##+# +# 1-9" "9"1 9-8(##*"09-8###*" *" 3",9$- -64& 4

17 Tecnoflon PTFE nanocomposites FKMs Main features / Applications: NFT 7030 P757/30M processability Excellent mechanical properties Permeation reduction: automotive industry (low emissions) Friction reduction: automotive industry (shaft seals, valve stem seals) chemical resistance: oil industry High purity: semicon / food industry P959/30M

18 Solexis FFKMs: Tecnoflon PFR

19 FFKM: Chemical structure F F F F F F - C - C C -C C -C - F F n F O m F X z TFE CF 3 MVE Cure site monomer Perfluoroelastomers (FFKM) are basically TFE / MVE (PAVE) copolymers + CSM

20 FFKM: Thermal resistance FFKM 320 C Their thermal resistance is the highest one among rubbers!

21 FFKM: Chemical resistance Fluid type Typical example FFKM a FKM b Fluorine Content 72.5% 66% Aliphatic hydrocarbon Propane Excellent Excellent Aromatic hydrocarbons Benzene Excellent Excellent Organic acids Acetic acid Excellent Fair-good Inorganic acids Sulfuric acid Excellent Excellent Alcohols Methanol Excellent Fair-excellent Inorganic base Sodium hydroxide Excellent Poor-fair Organic base Aniline Excellent Fair Ethers MTBE Excellent Fair-poor Ketones Acetone Excellent Poor Nitrous oxidizers Ammonium nitrate Excellent Halogen oxidizers Chlorine Excellent Excellent Heat transfer fluids Ethylene glycol Excellent Excellent Oils & greases Mineral oil Excellent Excellent Halogenated refrigerants HFC-134a Fair-good Poor-fair Polar solvents Water Excellent Excellent Chemical resistance is by far improved with respect to FKM!

22 FFKM: Classification Differences in perfluoroelastomer performance are due to the different weak points nature (i.e. curing chemistry) F o Curing point: X-linking agent: Phenoxy groups Bisphenol AF F 3 C-C-CF 3 o F

23 X -CH 2 CH-CH 2 - FFKM: Classification Differences in perfluoroelastomer performance are due to the different weak points nature (i.e. curing chemistry) Curing point: X-linking agent: Halogen atoms (Br/I) TAIC 0 N 0 X -CH 2 CH-CH 2 - N 0 N X -CH 2 CH-CH 2 -

24 FFKM: Classification Differences in perfluoroelastomer performance are due to the different weak points nature (i.e. curing chemistry) CN R 4 Sn Curing point: X-linking reaction: Curing catalyst: Nitrile CN groups Triazine formation R 4 Sn, etc. N N N

25 Performances comparison 8 )=! ;"15 &! $2,5 *! $;,5 )0& &3,>$,,5 *! "-7 )=! ;-7 &! -,7 *! %6? % )=! &6? % Tecnoflon PFR grades are peroxide curable

26 Performances comparison Chemical resistance * & )= + ; < - + ; < - 86@ ; < - ; ; ; ( ; ; ; ; ; + < - ;

27 Tecnoflon PFR grades portfolio Grade Cross-linker Feature Max T ( C) PFR 91 TAIC Not a true FFKM - Chemical Resistance 230 PFR 94 TAIC Chemical Resistance 230 PFR 06HC TAIC Very high chemical resistance (strong amines) 230 All are peroxide curable! PFR 95HT Incorporated Very high thermal resistance 320 PFR 5910M Incorporated High purity - low hardness 320 PFR 5920M Incorporated High purity - medium hardness 320

28 Next Generation of Low Temperature Fluoroelastomers

29 Overview History of Low Temperature Fluoroelastomers MOVE - new Low Temperature Monomer Technology Tecnoflon VPL - a New Series of Low Temperature Grades Testing Data on VPL versus standard LT FKM Applications Examples

30 The Fluoroelastomer Challenge Could we have good low temperature properties and high chemical resistance as well? TR10 Performance High F wt% Target Current grades Low F wt% Chemical resistance

31 The Fluoroelastomer Challenge Low temperature performance and chemical resistance are dependent upon polymer composition Monomer VDF CH 2 =CF 2 HFP CF 2 =CF-CF 3 TFE CF 2 =CF 2 PMVE CF 2 =CF-O-CF 3 TR10 Effect Decrease Increase Increase Decrease Fluid Resistance Effect Decrease Increase Increase Slightly Decrease The only way to improve low temperature performance is to design a new monomer.

32 MOVE Monomer Solution HFP PMVE MOVE T g = 160 C T g = -8 C T g = -39 C CF 2 =CF CF 3 CF 2 =CF O CF 2 =CF O Fully Fluorinated Monomer CF 3 CF2 No weak point! O CF 3

33 -30 Unique Properties of MOVE monomer 2. T g of copolymer lower than two homopolymers Tg ( C) /T g = w A P AA /T ga + w B P BB /T gb + (w A P AB + w B P BA )/T gab PVDF PMOVE MOVE3 (mol%) Johnston eq. T gab = -55 C

34 Market Needs Automotive Lower Sealing Temperature (cold environments) High pressure generates Tg shift GDI engines require FKM with lower Tg compared to standard solutions Increased chemical resistance (biofuels) maintaining Low T performance Aerospace Low T Service combined with high thermal resistance Low T combined with Fuels and HTS oils compatibility FKM for low Temperature Sealing Oil & Gas Drilling in cold environments ED Resistance Chemical Resistance...with good process-ability as well!

35 MOVE Monomer Technology ) A </! /=38=< Tecnoflon VPL (45 MU) VPL (25 MU) VPL (45 MU) VPL (25 MU) TR10 ( C) ( Beside the 2 main family of -40 C and -30 C, the new MOVE monomer technology allows us to improve other FKMs in term of low T behaviour and chemical resistance.

36 MOVE Monomer Technology 50 Volume Swell in M15 23 C 40 PL -30 V (%) %F 68.5%F 10 VPL -40 VPL -30 PL %F Tr10 ( C)

37 Rheological Properties Compound recipe Polymer VPL Luperox 101XL 45 Drimix TAIC 75 ZnO MT N990 phr phr phr phr Product Name Polymer Viscosity ML 121 C Compound Viscosity ML 121 C MU MU Tecnoflon PL VPL VPL Small difference between Polymer and Compound viscosity: excellent process-ability MDR C ML MH Ts2 T50 T90 lb*in lb*in min min min 1,7 27, ,2 28, ,1 26, Excellent cure profile due to Solvay s Branching & Pseudo Living Polymerization Technology

38 Physical Properties Product Name L.T. -30 C VPL VPL Hardness Shore A pts Tensile Strength MPa % MPa Break % C-Set 200 C O-Rings #214, 25% def. % Sealing behavior has not been affected by the new monomer!!

39 Retention (%) Temperature of Retraction Due to correct monomer sequences in the polymer chain, TR10 and TR70 values are very close Example of bad low T relaxation behavior Temperature ( C) VPL VPL PL -30 C PL -24 C

40 Volume Swell (%) Fluid Testing in Ethanol Blends Fuel C: 60 C CE10: 60 C CE22: 60 C CE85: 60 C Ethanol: 60 C Superior fluid resistance Comparable fluid resistance as 70% fluorine terpolymer VPL VPL PL -30 C FKM 70% F (TR10 = -7 C)

41 Fluid Testing in Methanol Blends M15: 23 C M85: 40 C Methanol: 23 C Volume Swell (%) Comparable fluid Superior fluid resistance as 70% resistance fluorine terpolymer 20 0 VPL VPL PL -30 C PL -24 C FKM 70% F (TR10 = -7 C)

42 Fluid Testing in Additional Fuels PN-180: 60 C FAM B: 60 C Superior fluid resistance Volume Swell (%) VPL VPL PL -30 C PL -24 C FKM 70% F (TR10 = -7 C)

43 Fluid testing in Biodiesel 15,0 Volume Swell (%) 10,0 5,0 RME 150 C No problem also in Biodiesel! 0,0 Terpolymer 68.5% Bisphenol Curable (TR10 = -13 C) FKM 70%F (TR10 = -7 C) PL -24 PL -30 VPL 85540

44 Compression Set Testing for 70 hours Improved compression set resistance 200 C 150 C 23 C Compress Set (%) VPL VPL L.T. -30 C L.T. -24 C

45 Heat Aging Effect of heat 200 C 150% Retained mechanical properties 100% 50% 0% time (h) TS M100 EB HDS

46 Compression Stress Relaxation CSR via Elastocon at 150 C 100 % Retained Sealing Force Very Similar CSR to standard grades Hours VPL VPL PL -30 C PL -24 C

47 VPL Performance in Fuel System Sealing VPL -30 & VPL -40 versus standard PL -30 C Property Low Temperature Performance Fuel resistance Compression set CSR VPL VPL

48 Conclusions Breakthrough Monomer Technology (MOVE) Expanded low temperature performance of Fluoroelastomers Superior Chemical resistance compared to standard PL -30 C Chemical Resistance comparable to 70%F PC Excellent sealing behavior Very good process-ability

49 Base resistant technology

50 Tecnoflon BR grades Standard Technology: -(CF 2 -CF)-(CH 2 -CF 2 )-(CF 2 -CF)- Schmiegel Sequences: Weak point BR Technology: CF 3 CF 3 In order to reduce Schmiegel Sequences we can introduce Ethylene into VDF based polymers. -(CF 2 -CF)-(CH 2 -CF 2 )-(CF 2 -CF)-(CH 2 - CH 2 )- CF 3 CF 3 Protecting monomer

51 Base resistant materials FKM Type 5 definition accounts for our BR technology

52 BR 9151: Performance comparison FKM copo FKM Terpo BR 9151 TFE/P FFKM Aromatic Hydrocarbons Poor Fuels Poor Oil Methanol Poor Hydrogen Sulfide Poor Poor Steam Poor Amines Poor Poor Low Temperature Poor Poor

53 New BR 9171 Chemical resistance Cold flexibility BR 9151 BR 9152 BR 4152 BR 9171 New!

54 BR 9171 NEW A new grade with by far improved chemical resistance compared to BR 9151 was developed Application targets: Axle seals: Gear oil + 6% Sturaco additive (vs TFE/P) B"3" B"-" B"-$ )@ &" B: ) #CD$": $")!""%, +$ *! *+ #* *(!& ) ", +)";$B % B $ &* + $! >&"./-417"12>"-,5 3, $7 *', +",!&, &(, &", ;?, ":7!', &$, $,!,!, 2 3 +! & ' &:#, &, &, +, &, ",./-417",,,>"-,5 3, B7 #&, #!, A#", ;?, 37 +#, +#, A#", 2 3!! &:', &:$, &:(,

55 Thank you!

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