Radiation curable coating containing polyfluorooxetane
AssigneeOMNOVA Solutions Inc.
InventorsRaymond J. Weinert, Guillermina C. Garcia, James E. Robbins, Aslam Malik
Life of this patent
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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.
Claims19
An acrylate, or methacrylate, or allylic, terminated polymer (oligomer) which is copolymerizable with styrene, methyl methacrylate or N-vinyl pyrrolidone, said polymer comprising the reaction product of a) at least one polyol, b) at least one di or polyisocyanate, and c) at least one hydroxy alkyl acrylate, or methacrylate, or allylic, wherein either i) a and b are reacted to form an isocyanate terminated oligomer or polymer and said isocyanate terminated oligomer or polymer is reacted with c to form an acrylate, or methacrylate, or allylic, terminated oligomer or polymer 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, where said at least one polyol comprises at least 10 weight percent repeating units of the formula
- 4
- 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;
- or each Rf is the same or different and individually is an oxaperfluorinated polyether having from 4 to 60 carbon atoms
A process for forming a partially fluorinated acrylate, or methacrylate, or allylic, terminated oligomer comprising reacting a partially fluorinated polyoxetane containing polyol, optionally including non-oxetane repeating units either a) sequentially with a di or polyisocyanate forming an isocyanate terminated oligomer or polymer and then reacting that isocyanate terminated oligomer or polymer with a hydroxyl containing acrylate, or methacrylate, or allylic, and forming an acrylate, or methacrylate, or allylic, terminated polyoxetane oligomer or polymer or b) in a single step with an isocyanate functionalized acrylate, or methacrylate, or allylic, forming an acrylate, or methacrylate, or allylic, terminated polyoxetane oligomer or polymer.
An acrylate, or methacrylate, or allylic, terminated polymer which is copolymerizable with styrene, methyl methacrylate or N-vinyl pyrrolidone, said polymer comprising the reaction product of a) at least one polyol, b) at least one di or polyepoxy compound, and c) at least one hydroxy alkyl acrylate, or methacrylate, or allylic, wherein either i) a and b are reacted to form an epoxy terminated oligomer or polymer and said epoxy terminated oligomer or polymer is reacted with c to form an acrylate, or methacrylate, or allylic, terminated oligomer or polymer or ii) b is reacted with c to form an epoxy functionalized acrylate, or methacrylate, or allylic, which is then reacted with a to form a acrylate, or methacrylate, or allylic, terminated oligomer or polymer, where said at least one polyol comprises at least 10 weight percent repeating units of the formula
- 7
- 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;
- or each Rf is the same or different and individually is an oxaperfluorinated polyether having from 4 to 60 carbon atoms
A process for forming a partially fluorinated acrylate, or methacrylate, or allylic, terminated oligomer comprising reacting a partially fluorinated polyoxetane containing polyol, optionally including non-oxetane repeating units either a) sequentially with a di or polyepoxy compound forming an epoxy terminated oligomer or polymer and then reacting that epoxy terminated oligomer or polymer with a hydroxyl containing acrylate, or methacrylate, or allylic, forming an acrylate, or methacrylate, or allylic, terminated polyoxetain oligomer or polymer or b) in a single step with an epoxy functionalized acrylate, or methacrylate, or allylic, forming an acrylate, or methacrylate, or allylic, terminated polyoxetane oligomer or polymer.
A coating composition comprising;
- a) an acrylate, or methacrylate, or allylic, terminated oligomer or polymer with at least 10 weight percent of repeating units having the formula
- 9
- 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;
- or each Rf is the same or different and individually is an oxaperfluorinated polyether having from 4 to 60 carbon atoms
- b) at least one monomer copolymerizable with said acrylate, or methacrylate, or allylic, terminated oligomer, and
- c) optionally a free radical initiator which is activated by ultraviolet radiation, and
- d) optionally a polyfunctional acrylate, or methacrylate, or allylic, monomer, or oligomer.
Dependencies are inferred from the claim text.