Abstract
Acrylonitrile was copolymerized with 8-methacryloxy-quinoline in Dimethylformamide using azobisisobutyronitrile as initiator. The composition of the copolymers was determined by nitrogen analysis and the monomer reactivity ratios (r 1 and r 2 ) were calculated. Both the homopolymer and the copolymers was characterized by a variety of spectral and thermal methods. Thermogravimetry and differential thermal analysis data showed that the comonomer (MAQ) initiates the nitrile oligomerization reaction in the copolymer upon heating. A mechanism for the initiation of (MAQ) units in the nitrile copolymers was also proposed.
Highlights
MAQ was prepared by the reaction of 8-hydroxyquinoline with the corresponding acid chloride or by the reaction of 8-hydroxyquinoline with the corresponding acid as follows: 2.2.1 Acid chloride method (Ferrnti, 1974)
Thermogravimetry and differential thermal analysis data showed that the comonomer (MAQ) initiates the nitrile oligomerization reaction in the copolymer upon heating
After the complete addition of methacryloyl chloride, the reaction mixture was allowed to stand at room temperature for 3 h. the solvent was evaporated
Summary
Acrylonitrile (AN) was obtained from BDH (Toronto, Canada) and was purified by distillation before polymerization; 8-hydroxyquinoline was provided by (S.D.finechem.- Ltd., Mumbai, Indi) methacrylic acid (Aldrich) was distilled twice at reduced pressure; N,N-dicyclohexylcarbodiimide (DCCI) and azobisisobutyronitrile (AIBN) were from Merck (Darmstadt, Germany), Dimethylformamide (El gomheria, Cairo, Egypt) triethanolamine (S.D.finechem.- Ltd., Mumbai, Indi) and methacryloyl chloride (Aldrich). To a well-stirred solution of 8-hydroxyquinoline (14.5 g; 0.1 mol) and triethylamine (28.5 ml; 0.3 mol) in 350 ml of dry methylene chloride, 8.61 ml (0.1 mol) of methacryloyl chloride was added dropwise under cooling in ice bath (0 –5°C). After the complete addition of methacryloyl chloride, the reaction mixture was allowed to stand at room temperature for 3 h. The residue obtained was crystallized from diethyl ether (yield 80%, m.p. 50°C). To a well-stirred cooled solution (0–5°C) of 8-hydroxyquinoline (2.9 g; 1 mol) and methacrylic acid (3.44 ml; 2 mol) in 300 ml of dry methylene chloride, 4.12g (0.1 mol) of DCCI was added dropwise. The resulting solution was evaporated under reduced pressure and the solid product was crystallized from diethyl ether (yield 70%, m.p. 49-52°C)
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