Radiation curable coating containing polyfuorooxetane
AssigneeOMNOVA Solutions Inc.
InventorsRaymond J. Weinert, Guillermina C. Garcia, James E. Robbins, Aslam Malik
Life of this patent
Estimating the term…
Abstract
Acrylate, or methacrylate, or allylic, functionalized polyfluorooxetanes are disclosed for use in radiation curable coating compositions. These acrylate, or methacrylate, or allylic, functionalized polymers provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils. The partially or fully fluorinated side groups of the fluorooxetanes are believed to be disproportionately present at the interfaces between the coating and the substrate and between the coating and the atmosphere.
Claims17
An acrylate, or methacrylate, or allylic, terminated oligomer, polymer, or copolymer comprising the reaction product of a) at least one polyfluorooxetane oligomer, or polymer, or copolymer polyol, b) at least one di or polyisocyanate, and c) at least one hydroxy alkyl acrylate, or hydroxy alkyl methacrylate, or hydroxy allylic, wherein either i) a) and b) are reacted to form an isocyanate terminated oligomer, or polymer, or copolymer, and said isocyanate terminated oligomer, or polymer, or copolymer is reacted with c) to form an acrylate, or methacrylate, or allylic, terminated oligomer, or polymer, or copolymer or ii) b) is reacted with c) to form an isocyanate functionalized acrylate, or methacrylate, or allylic, which is then reacted with a) to form an acrylate, or methacrylate, or allylic, terminated oligomer, or polymer, or copolymer, where said at least one polyfluorooxetane, oligomer, polymer, or copolymer polyol, comprises at least 10 weight percent repeating units of the formula
- where each n is the same or different and independently, is an integer between 1 and 5, R is hydrogen or an alkyl of 1 to 6 carbon atoms, and each Rf is the same or different and individually on each repeat unit is a linear or branched fluorinated alkyl of 1 to 20 carbon atoms, a minimum of 75 percent of the non-carbon atoms of the alkyl being fluorine atoms and optionally the remaining non-carbon atoms being H, I, Cl, or Br, where said acrylate, or methacrylate, or allylic terminated copolymer includes repeat units derived from tetrahydrofuran, and said acrylate, or methacrylate, or allylic, terminated oligomer, polymer, or copolymer being radiation curable.
A process for forming an acrylate, or methacrylate, or allylic, terminated oligomer, polymer, or copolymer, comprising reacting a polyfluorooxetane oligomer, polymer, or copolymer polyol either i) sequentially with a di or polyisocyanate forming an isocyanate terminated oligomer, or polymer, or copolymer and then reacting said isocyanate terminated oligomer, or polymer, or copolymer with a hydroxyl containing acrylate, or hydroxyl containing methacrylate, or hydroxyl containing allylic, and forming an acrylate, or methacrylate, or allylic, terminated polyfluorooxetane oligomer, or polymer, or copolymer, or ii) in a single step with an isocyanate functionalized acrylate, or methacrylate, or allylic, and forming an acrylate, or methacrylate, or allylic, terminated polyfluorooxetane oligomer, or polymer, or copolymer;
- said acrylate, or methacrylate, or allylic, terminated polyfluorooxetane oligomer, or polymer, or copolymer being radiation curable;
- and wherein said polyfluorooxetane oligomer, or polymer, or copolymer polyol comprises at least 10 weight percent repeating units of the formula
- where each n is the same or different and independently, is an integer between 1 and 5, R is hydrogen or an alkyl of 1 to 6 carbon atoms, and each Rf is the same or different and individually on each repeat unit is a linear or branched fluorinated alkyl of 1 to 20 carbon atoms, a minimum of 75 percent of the non-carbon atoms of the alkyl being fluorine atoms and optionally the remaining non-carbon atoms being H, I, Cl, or Br, and wherein said acrylate, or methacrylate, or allylic terminated copolymer includes repeat units derived from tetrahydrofuran.
An acrylate, or methacrylate, or allylic, terminated oligomer, or polymer, or copolymer, which is copolymerizable with styrene, methyl methacrylate or N-vinyl pyrrolidone, said oligomer, polymer, or copolymer comprising the reaction product of a) at least one polyfluorooxetane, oligomer, polymer, or copolymer polyol b) at least one di or polyisocyanate, and c) at least one hydroxy alkyl acrylate, or hydroxy alkyl methacrylate, or hydroxy allylic, wherein either i) a) and b) are reacted to form an isocyanate terminated oligomer, or polymer, or copolymer, and said isocyanate terminated oligomer, or polymer, or copolymer is reacted with c) to form an acrylate, or methacrylate, or allylic, terminated oligomer, or polymer, or copolymer or ii) b) is reacted with c) to form an isocyanate functionalized acrylate, or methacrylate, or allylic, which is then reacted with a) to form an acrylate, or methacrylate, or allylic, terminated oligomer or polymer, or copolymer, where said at least one polyfluorooxetane oligomer, polymer, or copolymer polyol comprises at least 10 weight percent repeating units of the formula
- where each n is the same or different and, independently, is an integer between 1 and 5, R is hydrogen or an alkyl of 1 to 6 carbon atoms, and each Rf is the same or different and individually on each repeat unit is a linear or branched fluorinated alkyl of 1 to 20 carbon atoms, a minimum of 75 percent of the non-carbon atoms of the alkyl being fluorine atoms and optionally the remaining non-carbon atoms being H, I, Cl, or Br, where said acrylate, or methacrylate, or allylic terminated copolymer includes repeat units derived from tetrahydrofuran, and said acrylate, or methacrylate, or allylic, terminated oligomer, polymer, or copolymer being radiation curable.
Dependencies are inferred from the claim text.