Methods of digital printing using modified indigo compounds
A technology of digital printing and dye compounds, applied in chemical instruments and methods, applications, dyeing methods, etc., can solve the problems of not being suitable for printing denim, changing the feel of fabrics, etc.
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Embodiment 1
[0502] Embodiment 1: the synthesis of compound 2 and 6
[0503]
[0504] In an inert atmosphere (Ar or N 2 ), in a 1.0L glass bottle equipped with a condenser and a mechanical stirrer, isonicotinoyl chloride (92g , 0.515mol, 2.5 equivalents). The reaction mixture was heated to 50° C. for 6 h (reaction progress followed by TLC (5% MeOH in DCM, Rf 0.5)). After this time, the dark red / pink reaction mixture was allowed to cool and most of the pyridine was removed under vacuum. The resulting reaction mixture was quenched by pouring into cold water (500 mL) and stirred for 30 minutes. The solid precipitate thus formed was isolated by filtration and washed well with cold water. The dark red solid was dried under vacuum, then dissolved in dichloromethane (1 L); the solution was further dried using anhydrous sodium sulfate. The dark red solution was filtered and concentrated to dryness under vacuum to give a dark purple / red solid (60 g, 61.8% yield). pass 1 Characterization b...
Embodiment 2
[0507] Embodiment 2: the synthesis of compound 28
[0508]
[0509] In an inert atmosphere (Ar or N 2 ), in a flask equipped with a condenser and a mechanical stirrer, 2-nicotinoyl chloride (14.2 g, 80 mmol, 4 equivalents). The brown reaction mixture became very viscous and warm and was stirred at room temperature for 30 mins, then gradually heated to 50 °C (followed by TLC (5% MeOH in DCM, Rf 0.3)). The resulting reaction mixture was quenched by pouring into cold water (200 mL) and stirred for 30 minutes. The solid precipitate isolated by filtration proved to be unreacted indigo. The aqueous phase was extracted into dichloromethane (3 x 50 mL), dried and concentrated to give a brown solid which was purified using flash column chromatography. The main product was isolated as a yellow solid (yellow on TLC, Rf = 0.3 as above) and characterized by NMR. This analysis is inconsistent with the above structure, showing that the 2-derivative behaves quite differently than the 3-...
Embodiment 3
[0511] Embodiment 3: the synthesis of compound 15
[0512]
[0513] In an inert atmosphere (Ar or N 2 ), in a flask equipped with a condenser and a mechanical stirrer, add isonicotinoyl chloride (13 g, 0.076 mol) in batches to a suspension of anhydrous pyridine (100 mL) containing indigo (20 g, 0.076 mol) under high-efficiency stirring , 1 equivalent). The reaction mixture was heated to 50° C. for 6 h (reaction progress was followed by TLC (with 5% MeOH in DCM, Rf 0.6); TLC also showed some disubstituted product). After this time, the dark red / pink reaction mixture was allowed to cool and most of the pyridine was removed under vacuum. The resulting reaction mixture was quenched by pouring into cold water (500ml) and stirred for 30 minutes. The solid precipitate thus formed was isolated by filtration and washed well with cold water. The dark red solid was dried under vacuum, then dissolved in dichloromethane (1 L); this solution was further dried over anhydrous sodium su...
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