Nanostrength Block Copolymers for Epoxy Toughening

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1 Nanostrength Block Copolymers for Epoxy Toughening PABu 100 nm PMMA PMMA / Epoxy

2 Nanostrength for epoxy toughening Arkema Overview Nanotechnology Platform at Arkema NANOSTRENGTH Block Copolymers for Epoxy Value Drivers Epoxy Toughening with NANOSTRENGTH Range of properties achievable using NANOSTRENGTH How it works Application Specific Properties- Composites and Adhesives 2

3 Arkema 2007 overview Sales by region Sales: 5.7 bn ($8.5B) Europe (excl. France) 39% North America 25% Capital employed: 3.1 1bn Capex: 4% of sales France 18% Row 5% Asia 13% Sales per year 2007 R&D: 3% of sales 15,200 employees In bn

4 R&D accelerates product innovation Overview (2007) R&D by segment 3% of sales Breakthrough 1,350 researchers Near 100 joint projects with universities 6 R&D centers Portfolio around 5,700 patents Vinyl Products Industrial Chemicals 12% 12% 25% 51% Performance Products 2005 Recent breakthroughs 4

5 Nanotechnology Platform at Arkema CRP* initiator & FlexiBloc CRP* macroinitiator Our customers : Compounds, Thermosets, Pigments, Engineering resins, Paints, Coatings, Adhesives, Block Copolymers Functionalized Specialty Block Copolymers & FlexiBloc Reactive Block Copolymer 5

6 Nanotechnology Platform at Arkema Block copolymers for epoxy toughening 6

7 Classical vs. Controlled Free Radical Classical Radical Polymerization No control of termination Wide polydispersities Random sequencing of monomer units Controlled Radical Polymerization Living chain ends experience reduced termination Reduced polydispersities Block copolymers possible 7

8 Complete Control of Block Structure Block copolymers Classical Block copolymers Random copolymer Diblock copolymer ABA triblock copolymer ABC triblock copolymer Incompatibility between blocks organization at the nanometer scale 8

9 Nanostrength Triblock Polymers Controlled Radical Polymerization (CRP) ABA, AB Poly[(Methyl)methacrylate] l) l t -b- poly(butyl lacrylate) -b- poly[(methyl)methacrylate] l) l t Poly[(Styrene] -b- poly(butyl Acrylate) -b- poly[(styrene] Functional comonomers can be added (AA, MAA, PEGMA, HEMA, ) Anionic polymerization SBM polystyrene -b- polybutadiene -b- poly[(methyl)methacrylate] Outstanding control of molecular weight, molecular weight distribution, composition, chain architecture, functionalization 9

10 Block Copolymers for Epoxy Toughening Structural Adhesives (Automotive, Industrial, Assembly, Wind Energy, Electronics ) Coating (Solvent, Powder, ) Composites (Aerospace, Sports and Leisure, ) Epoxy compounds Nanostrength is suited for every application that needs an increase in resistance to crack propagation while maintaining Tg and Modulus of the systems. Due to the unique nanostructuration achievable with Nanostrength, it is possible to achieve identical toughness to competitive e modifiers (CTBN) but using reduced loading levels. 10

11 Block Copolymers for Epoxy Toughening Advantages of Nanostrength : Toughening with little loss of Tg or Modulus Outstanding toughening at lower loading due to unique modifier morphologies Ease of Processing- additive dissolves in epoxy resin Nanoscale self-assembled particles allow for toughening of: 1. Thin adhesive bond lines 2. Thin coatings 3. Composites with small inter-fiber spacing CTBN / TP Core-Shell Nanostrength 0.1 ~ 0.8 µm 1 ~ 5 µm 10 ~ 100 nm 11

12 Block Copolymers for Epoxy Toughening Low Tg systems: DGEBA + Jeffamine TM T403 M53 CTBN Loading Level K1C G1C Tg K1C G1C Tg 0% % % % % Superior toughening at equivalent loadings Equivalent toughening at lower loadings 12

13 Block Copolymers for Epoxy Toughening Intermediate Tg systems: DGEBA + DICY M52N CTBN Loading Level K1C Tg K1C Tg 0% % TBD 5.00% % Dicyandiamide (Dicy) is hardener representative of: - Adhesives - Sports and Leisure composites - Coatings 13

14 A Self-assembling Nanotechnology - Affinity between epoxy monomers and PMMA - Repulsion between epoxy monomers and the middle block(s) Nanophase separation of PBuA blocks: M - A - M DGEBA PABu PMMA PMMA / Epoxy PABu PMMA / Epoxy PMMA 14

15 Toughening of epoxy systems Many mechanisms contribute to epoxy toughness : Shear yielding Multiple crazing Crack pinning Crack bridging Crack deflection. Toughening is more than flexibilization. Flexibilization lowers the modulus of the material to decrease brittleness (CTBN - flexibilizer) by reacting to the backbone of the epoxy. Nanostrength (and core shells) maintain i modulus while toughening. Pearson (1993) Huang, Y., and Kinloch, A.J., J. Mater. Sci., 27, 2763 (1992). 15

16 Toughening of epoxy systems The most efficient mechanisms to toughen are system & condition dependant: Low Tg systems, high T or low speed testing conditions: Shear yielding Matrix network has enough mobility to activate plasticity High Tg systems, low T or high speed testing conditions: Multiple crazing Matrix network too cross-linked to Crack bridging activate plasticity Crack pinning i Crack deflection R.A. Pearson, "An overview of organic toughening agents for epoxy resins", ERFD Spring 2000 Conference, April 16-18, 2000, San Antonio, TX 16

17 Toughening of epoxy systems Existing tougheners have specific toughening mechanisms: Liquid reactive rubbers shear yielding Thermoplastics crack bridging, pinning & deflection Acrylic block copolymers: all mechanisms Shear Yielding (cavitation of the rubber phase) Nanoscale modifiers lead to high density of shear band formation Unique morphologies lead to better toughening Crack Bridging Crack Pinning (strong matrix adhesion) Crack Deflection 17

18 Toughening of epoxy systems Cavitation of nanodomains 18

19 Toughening of epoxy systems Modifier morphology in cured epoxy dependent on: Crosslinking/Resin chemistry Block Copolymer Chemistry M51, M52, M53: PMMA-block-PBuA-block-PMMA DGEBA + M-DEA DEGBA + Jeffamine T403 19

20 Toughening of epoxy systems Block Copolymer Chemistry dictates Modifier Morphology DGEBA + DDS Ref +10% MAM exp1 +10% MAM exp2 +10% MAM M22N MAM exp1 5µm MAM exp2 3µm Development of functionalized grades to further improve nanostructuration with all types of epoxy systems: M22N or M52N: PMMA/DMA-block-PBuA-block-PMMA/DMA PBuA M22N 2µm 20

21 Toughening of epoxy systems Modifier Morphology dictates Properties Low Tg systems DGEBA + Jeffamine T403 M22N gives excellent nanostructuration for perfect transparency M53 gives spider web agglomeration for superior toughening Neat Epoxy M22N K 1C M53 G 1C

22 Toughening of epoxy systems Low Tg systems DGEBA + Jeffamine T403 Plastic Deformation of the samples with block copolymers e (N) Forc Neat 10% M53 10% CTBN Displacement (mm)

23 Toughening of epoxy systems Balance of properties: Fluidity at 80 C Superior DGEBA+ Jeffamine T toughening with 0.8 some viscosity 0.6 penalty with 10% Tg Fluidity at 40 C 0.4 M53 or Equivalent viscosity and toughening, g, improved Tg and modulus at ¼ of the loading GIC KIC E Neat 10% CTBN 10% M53 2.5% M53 23

24 Block Copolymers for Epoxy Toughening Intermediate Tg systems: DGEBA + DICY M52N CTBN Loading Level K1C Tg K1C Tg 0% % TBD 5.00% % K 1C = 1.54 K 1C = 1.82 Nanospherical micelles for perfect transparency (exp. grade) M52N gives worm-like micelle structure for excellent toughening 24

25 Toughening of epoxy systems Balance of properties: Fluidity at 40 C Superior CTBN 10% toughening and M52N 10% Tg at equivalent M52N 5% loading Neat Tg Fluidity at 80 C Equivalent toughening and viscosity with enhanced Tg at ½ of the loading KIC E 25

26 Nanostrength for Epoxy Toughening 160 C cure K IC (MPa.m 0.5 ) T ( C) Reference Even greater advantages with Nanostrength in more toughenable DICY cured systems lower cure temperature 10% M52N % CTBN higher Epoxy Equivalent Weight (EEW) resin 2.5 DGEBA/DICY study done with Ray Pearson, Lehigh University Neat 10%M52N 10% CTBN X 8 10% CTBN X13 2 K1C DGEBA EEW 26

27 Toughening of epoxy systems High Speed Impact Resistance DGEBA + Dicyandiamide (DICY) Impact Testing Energy Absorbed (J) More than 2X improvement in impact energy (CEAST Fractovis dart drop) with block copolymers % improvement in peak force at break. 0 Neat M52N- 10% CTBN-10% 27

28 Toughening of epoxy composites High Tg systems RTM6 DGEBA + M-DEA M53 Loading Level K1C G1C Tg 0% % DGEBA + DDS 0.0 M52N Loading Level K1C G1C Tg 0% % Tg Fluidity at 100 C Fluidity at 120 C Neat M51 M52 PSU Excellent toughening and good maintenance of Tg KIC E M51, M52: Lower MW MAM meets RTM specs for viscosity 28

29 Toughening of epoxy adhesives Lap Shear Strength (MPa a) Neat Nanostrength-10% CTBN-10% 0 Study done by Rescoll laboratories DICY Jeffamine D230 DETA No detrimental effect on adhesion in DICY and polyetheramine (Jeffamine D230) cured epoxies while maintaining Tg and improving fracture toughness Significant improvement in lap shear strength in diethylene triamine (DETA) cured epoxies 29

30 Toughening of epoxy systems Dissolution of block copolymers in epoxy Dissolution time in low Mw epoxy resin 90 C 135 C Block copolymers will dissolve in epoxy resin; no need for dispersion Time (min) Block copolymers dissolve quickly at elevated temperatures with minimal shear M52 M53 M52N Transparency of solution does not always indicate dissolution! 30

31 SBM Block Copolymers for Epoxy Toughening PMMA block gives excellent compatibility to epoxy systems which are less polar (similar to non-functionalized MAM) Butadiene block has a lower Tg (-70 C) ) than butylacrylate y (-40 C) so improved toughening at lower temperatures possible Higher differences in chi parameters allows for shorter (lower MW) block copolymers to still nanostructure -> Lower viscosity yproducts possible Neat Epoxy E21 E41 DGEBA/Jeffamine Tg TBD K 1C TBD G 1C TBD DGEBA/MDEA Tg K 1C G 1C 258 TBD 418 Phenolic Novolac Tg 175 TBD 180 K 1C 0.63 TBD 0.86 G 1C 152 TBD

32 Toughening of epoxy systems Advantages: Superior Toughening to competitive products Equivalent toughening at much lower loadings ($ advantages) Versatile block copolymer chemistry allows for the proper grade to be selected for given epoxy systems Balance of Properties: Limited loss of Tg and Modulus High reproducibility (controlled by Thermodynamic)/ no need for dispersion Drawbacks: Need to dissolve at high h temperature in epoxy Increase of viscosity (mitigated by use at lower loadings) 32

33 Commercial Nanostrength Grades SBM grades E21 - Medium MW with high butadiene content, good for structural applications; excellent toughening with PMMA friendly cross-linking agents (Jeffamine, MDEA) E41 - Low MW with medium butadiene content, low increases in viscosity, good for electronic or viscosity sensitive applications MAM grades M52- medium MW, low viscosity M53-High molecular weight, excellent toughening with PMMA friendly cross-linking agents (Jeffamine, MDEA) M52N- Functionalized MAM; best toughening with PMMA unfriendly crosslinking agents (DICY, DDS); composite and adhesive applications M22N- Highly functionalized MAM for excellent compatibility and nanostructuration (transparent applications or highly polar systems) 33

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