Blocked bio-based carboxylic acids and their use in thermosetting materials
a bio-based carboxylic acid and thermosetting technology, applied in the field of bio-based polyfunctional carboxylic acids, can solve the problems of limited maximum degree of substitution (ds), resins that have not been commercialized, and performance properties inferior to those of current petrochemical based technology, and achieve excellent hardness, solvent resistance, adhesion, and flexibility.
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example 1
[0066]Synthesis of blocked-azelaic acid compounds (Table 5). In a 50-mL single neck round bottom flask, azelaic acid (5.00 g, 0.0266 mol) was combined with 4 molar equivalents (0.106 mol) of the appropriate vinyl ether compound (7.66 g of ethyl vinyl ether, 9.15 g of propyl vinyl ether, or 10.64 g of butyl or isobutyl vinyl ether). To this mixture, solid phosphoric acid (0.017 g, 0.177 mmol) was added. The mixture was stirred for 5 hours at a temperature dependent on the vinyl ether compound used (30° C. for ethyl vinyl ether, 70° C. for propyl vinyl ether, or 80° C. for butyl or isobutyl vinyl ether). After the reaction mixture cooled to room temperature, it was transferred to a 125-mL separatory funnel, where 40 mL of 0.05 M KOH was added. The funnel was capped and shaken to extract the phosphoric acid. The organic layer was isolated, and rotary evaporation was used to remove the excess vinyl ether. Blocked-azelaic acid compounds were recovered in 84-94% yield. Example 1H NMR data...
example 2
[0067]Synthesis of blocked-succinic acid compounds (Table 5). The procedure used for blocking azelaic acid compounds was used for their succinic acid equivalents, using 5.00 g succinic acid and the properly adjusted amounts of vinyl ether and phosphoric acid. Example 1H NMR data for propyl vinyl ether blocked succinic acid (CDCl3, δ, ppm): 0.83 (triplet, 6H, —CH3), 1.30 (multiplet, 4H, O—CH(CH2)—O), 1.50 (quartet, 4H, O—CH2-CH2—CH3), 2.56 (triplet, 4H, O2C—CH2—CH2—CO2), 3.33 (quartet, 4H, O—CH2—CH2-CH3), 5.86 and 5.87 (s, 2H, O—CH(CH2)-O). The presence of other peaks suggests that the product is 3:1 mixture of two blocked carboxylic acids per molecule to one blocked carboxylic acid per molecule.
example 3
[0068]Synthesis of blocked-citric acid compounds (Table 5). In a 50-mL single neck round bottom flask, citric acid (5.00 g, 0.0260 mol) was combined with 6 molar equivalents (0.156 mol) of the appropriate vinyl ether compound (13.45 g of propyl vinyl ether or 15.64 g of butyl or isobutyl vinyl ether). To this mixture, solid phosphoric acid (0.026 g, 0.260 mmol) was added. The mixture was stirred for 18 hours using the same temperatures used for the block-azelaic acid synthesis. The phosphoric acid was extracted using 40 mL of 0.05 M KOH, and the excess vinyl ether was removed via rotary evaporation. Blocked-citric acid compounds were recovered in 84-94% yield.
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