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2015|16 Annual Report Fraunhofer IGB

92 Background and aims of project Large quantities of terpenes are a by-product of the produc- tion of cellulose. To date, these substituted cyclic or bicyclic, partially functionalized hydrocarbons are still mainly thermally utilized. The aim of the research described here was to continue the development of the use of terpene lactams as building blocks for biobased polyamides, as presented in the 2014 Annual Report. In addition to camphor, which can be converted into a monomer in only one synthetic step thanks to the carbonyl group that is already present in the molecule, we also investigated 3-carene, one of the main constituents in turpentine oil. Synthesis of carane lactam 3-carene is also a bicyclic terpene. However, the carbonyl group that is re uired for the synthesis of a lactam must first be produced through oxidation of the double bond in the molecule. In contrast to camphor lactam, the lactam that is derived from 3-carene (carane lactam) would appear to be simpler to polymerize as the second cycle is at a longer distance from the functional group required for polymeriza- tion. This ensures lower steric hindrance which is, however, still adequate for the expected properties of the polymer, as is indicated by DSC analysis (differential scanning calorimetry). Polymerization of carane lactam The conversion of the lactam can be carried out by anionic polymerization, analogous to the production of polyamide 6 (reaction in mold, RIM). In contrast to the hydrolytic po- lymeri ation where the lactams are opened in a first step to aminocarbonicacids in the anionic case the chain formation proceeds directly from the monomer in the presence of a catalyst and an activator. Carane lactam polymerizes within a few minutes at temperatures of approx. 220°C. We can hereby obtain a transparent polymer that has no melting point based on differential scanning calorimetry (DSC) (Fig. 2). This indicates that only minimal crystalline regions remain. Advantages of the new polyamides Most biopolymers are produced from sugar and starch and are thus in direct competition with the food supply. Converse- ly, the current case involves utilizing waste products. Based on the sterically complex substituted cycle between the amide bonds – in contrast to typical partially crystalline standard polymers – we obtain materials that mainly have amorphous properties and enable new applications due to their transpar- ency, for example, for the manufacture of ski goggles. CHEMISTRY DEVELOPMENT OF TRANSPARENT HIGH-PERFORMANCE POLYAMIDES FROM WOOD INDUSTRY WASTE PRODUCTS Harald Strittmatter, Dominik Pastötter, Paul Stockmann, Volker Sieber 1 C a r a n l a c t a m ( ) n 3 - C a r e n a u f 3 - C a r e n b a s i e r t e s P o l y a m i dC a r a n l a c t a m ( 3 - C a r e n a u f 3 - C a r e n b a s i e P o l y a m i d C a r a n l a c t a m ( ) n 3 - C a r e n a u f 3 - C a r e n b a s i e r t e s P o l y a m i dcarane lactam C a r a n l a c t a m ( ) n 3 - C a r e n a u f 3 - C a r e n b a s i e r t e s P o l y a m i dpolyamide based on 3-carene C a r a n l a c t a m ( ) n 3 - C a r e n a u f 3 - C a r e n b a s i e r t e s P o l y a m i d3-carene