Dye conjugation to linseed oil by highly-effective thiol-ene coupling and subsequent esterification reactions

作者：Hayashi Toshiki; Kazlauciunas Algy; Thornton Paul D^*

来源：Dyes and Pigments, 2015, 123: 304-316.

DOI：10.1016/j.dyepig.2015.07.023

• Renewable resources
• Linseed oil
• C. I. Disperse Red 1
• Thiol-ene chemistry
• Dye conjugation
• Coloured coatings

Linseed oil, a renewable material obtained from the ripened seeds of the flax plant, was conjugated with C. I. Disperse Red 1 to yield a coloured macromolecule in two experimentally-simplistic coupling steps. Firstly, the abundant presence of carbon carbon double bonds in linseed oil was exploited to introduce carboxylic acid functionality to linseed oil via a thiol-ene reaction between linseed oil and 3-mercaptopropionic acid. C. I. Disperse Red 1 was then grafted to the carboxylic acid units now present via esterification, offering a coloured product in high yields. On average, 39.2% of the carbon carbon double bonds in each linseed oil molecule were furnished with a C. I. Disperse Red 1 molecule. The remaining carbon carbon double bonds may therefore be further exploited for chemical crosslinking, ensuring that the product formed is of potential significance as a coloured, bio-based, surface coating product.

• 出版日期2015-12