Abstract
Several synthetic strategies based on the use of substituted aromatic and hetero-aromatic thiols for the covalent binding of modifier compounds to PVC are described. A variety of aliphatic alcohols and amines are linked to the aromatic or heteroaromatic rings via highly active functionalities as the isocyanate, acidchloride, or chlorosulfonyl group, and the three chlorine atoms of trichlorotriazine. The first three pathways lead to protected aromatic disulfides obtaining the substituted aromatic thiols by reduction as a final step of an unprecedented synthetic route. The second approach, in a novel, extremely efficient, and scalable process, uses the particular selectivity of trichlorotriazine to connect aliphatic amines, alcohols, and thiols to the ring and creates the thiol via nucleophilic substitution of a heteroaromatic halogen by thiourea and subsequent hydrolysis. Most of the modifier compounds were linked to the polymer chains with high degrees of anchorage. The presented approaches are highly versatile as different activations of aromatic and heteroaromatic rings are used. Therefore, many types of tailored functional nucleophiles may be anchored to PVC providing non-migrating materials with a broad range of applications and properties.
Highlights
Poly(vinyl chloride), PVC, is one of the most versatile plastics of the modern world and places second in the market share of polymeric materials [1,2]
In this article we present and analyze novel synthetic approaches based on the use of aromatic and hetero-aromatic thiols for the covalent linkage of model molecules to PVC
It is well known that a very efficient and selective way to link molecules to the PVC chains is the nucleophilic substitution of its chlorine atoms using aromatic or hetero-aromatic thiol compounds [20].In what follows, we have tested different preparative approaches on how aromatic and hetero-aromatic thiols with aliphatic chains in ortho, meta, and/or para-position can be synthesized and linked to PVC in the most efficient manner
Summary
Poly(vinyl chloride), PVC, is one of the most versatile plastics of the modern world and places second in the market share of polymeric materials [1,2]. Around 35% of PVC produced in the world is used for the production of soft-PVC articles which contain large amounts of plasticizers yielding inexpensive articles useful for applications in the cables and films industry, as children toys, kitchen floors, or biomedical devices, such as blood bags, catheters, protective gloves, etc. Dioctyl phthalate (DOP), one of the most frequently used plasticizers for PVC, was shown to produce toxic and adverse effects, especially in animal or human tissues, such as the pituitary gland, liver, or testicles [6,7] For this reason, DOP was banned a few years ago for certain applications by the U.S Consumer Product Safety Commision (CPSC)
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