UV curable, liquid diacrylate monomers based on (cis,trans)-1,3/1,4-cyclohexanedimethanol

Abstract

Novel, liquid cycloaliphatic diacrylate monomers based on (cis,trans)-1,3/1,4-cyclohexanedimethanol have been synthesized for use in ultraviolet (UV)- and electron beam (EB)-cured coatings, inks, and adhesives. Diacrylate monomers prepared from this unique diol, and containing less than 15 wt% trans-1,4-cyclohexanedimethanol diacrylate, are liquid at room temperature and readily soluble in other acrylate monomers and oligomers (in contrast to diacrylates prepared from 1,4-cyclohexanedimethanol, which are solid). More importantly, UV-cured coatings based on (cis,trans)-1,3/1,4-cyclohexanedimethanol diacrylates (1,3/1,4-CHDMDA) show superior hardness, scratch resistance, and chemical resistance as compared to common diacrylate monomers used in the UV coating industry such as tripropylene glycol diacrylate, hexanediol diacrylate, dipropylene glycol diacrylate, and propoxylated neopentyl glycol diacrylate. Thus, this new monomer appears to be a promising material for enhancing the performance of radiation-cured coatings, inks, and adhesives applied to a variety of substrates, including plastic, paper, wood, metal, and glass. This paper will summarize the synthesis of liquid diacrylates from (cis,trans)-1,3/1,4-cyclohexanedimethanol, as well as the performance properties of the corresponding UV-cured coatings.