Toner compositions

Abstract

The present disclosure provides for enzymatic polymerization to produce polyester resins suitable for use in manufacturing toners. In embodiments, crystalline copolymers, which are polyesters, may be synthesized from lactones, cyclic anhydrides, cyclic carbonates, and combinations thereof. These crystalline copolymers, in turn, may be utilized in the synthesis of toner particles.

1 . A process for preparation of crystalline polyesters comprising:
 contacting at least one component selected from the group consisting of lactones, lactides, cyclic anhydrides, cyclic carbonates, and combinations thereof, with an enzyme selected from the group consisting of lipases, cutinases, and combinations thereof;   polymerizing the at least one component to form a crystalline polyester resin;   recovering the crystalline polyester resin;   contacting the crystalline polyester resin with an optional amorphous resin, an optional colorant, an optional wax, and an optional surfactant to form toner particles; and   recovering the toner particles,   wherein the toner particles are suitable for cold pressure fusing.   
     
     
         2 . A process as in  claim 1 , wherein the lipase is obtained from an organism selected from the group consisting of  Pseudomonas aeruginosa, Pseudomonas cepacia, Pseudomonas fluorescens, Aspergillus niger, Candida antarctica, Candida cylindracea, Klebsiella oxytota , and  Mucor meihei.    
     
     
         3 . A process in  claim 1 , wherein the lipase is selected from the group consisting of lipase PA, lipase PC, lipase PF, lipase A, lipase CA, lipase B, lipase CC, lipase K, lipase MM, and combinations thereof. 
     
     
         4 . A process as in  claim 1 , wherein the lactone is selected from the group consisting of caprolactone, pentadecalactone, hexadecenlactone, pentadecenlactone, 7-Hexadecen-16-olide, dodecalactone, and combinations thereof. 
     
     
         5 . A process as in  claim 1 , wherein the cyclic anhydride is selected from the group consisting of succinic anhydride, glutaconic anhydride, maleic anhydride, cyclopentane-1,2-dicarboxylic anhydride, cyclohexene-1,2-dicarboxylic anhydride, 3-bicyclo[2,2,2]octadicarboxylic anhydride, phthalic anhydride, naphthalene-dicarboxylic anhydride, pyridine-dicarboxylic anhydride, thiophene-dicarboxylic anhydride, and combinations thereof. 
     
     
         6 . A process as in  claim 1 , wherein the cyclic carbonate is selected from the group consisting of trimethylene carbonate, carboxytrimethylene carbonate, esters of carboxytrimethylene carbonate, and combinations thereof. 
     
     
         7 . A process as in  claim 1 , wherein the polyester resin comprises pentadecalactone in combination with pentadecenlactone. 
     
     
         8 . A process as in  claim 1 , further comprising forming the polyester resin at a temperature of from about 10° C. to about 100° C. for a period of time of from about 1 minute to about 72 hours, and wherein particles comprising the polyester resin possess a melting point of from about 55° C. to about 95° C., and a molecular weight of from about 1,000 to about 50,000. 
     
     
         9 . A process as in  claim 1 , wherein the cold pressure fusing occurs by applying the toner particles to a substrate and fixing them to the substrate at a temperature of from about 20° C. to about 50° C. by application of pressure of from about 3 kpsi to about 10 kpsi, wherein the toner particles remain fixed to a substrate and do not smear. 
     
     
         10 . A process comprising:
 contacting at least one component selected from the group consisting of lactones, lactides, cyclic anhydrides, cyclic carbonates, and combinations thereof, with an enzyme selected from the group consisting of lipases, cutinases, and combinations thereof;   polymerizing the at least one components to form a crystalline polyester resin;   recovering the crystalline polyester resin;   contacting the crystalline polyester resin with an optional amorphous resin, an optional colorant, an optional wax, and an optional surfactant to form toner particles;   recovering the toner particles;   applying the toner particles to a substrate; and   fixing the toner particles to the substrate at a temperature of from about 20° C. to about 50° C. by application of pressure of from about 3 kpsi to about 10 kpsi.   
     
     
         11 . A process in  claim 10 , wherein the lipase is selected from the group consisting of lipase PA, lipase PC, lipase PF, lipase A, lipase CA, lipase B, lipase CC, lipase K, lipase MM, and combinations thereof. 
     
     
         12 . A process as in  claim 10 , wherein the lipase is immobilized on a support member selected from the group consisting of porous polymer beads, acrylic resins, cross-linked polystyrene, ceramics, and combinations thereof. 
     
     
         13 . A process as in  claim 10 , wherein the lactone is selected from the group consisting of caprolactone, pentadecalactone, hexadecenlactone, pentadecenlactone, 7-Hexadecen-16-olide, dodecalactone, and combinations thereof, wherein the cyclic anhydride is selected from the group consisting of succinic anhydride, glutaconic anhydride, maleic anhydride, cyclopentane-1,2-dicarboxylic anhydride, cyclohexene-1,2-dicarboxylic anhydride, 3-bicyclo[2,2,2]octadicarboxylic anhydride, phthalic anhydride, naphthalene-dicarboxylic anhydride, pyridine-dicarboxylic anhydride, thiophene-dicarboxylic anhydride, and combinations thereof, and wherein the cyclic carbonate is selected from the group consisting of trimethylene carbonate, carboxytrimethylene carbonate, esters of carboxytrimethylene carbonate, and combinations thereof. 
     
     
         14 . A process as in  claim 10 , further comprising contacting the at least one component and enzyme with a coalescence inhibitor selected from the group consisting of alkanes, cycloalkanes, long chain alcohols, halogenated hydrocarbons, organosilicon compounds, long-chain esters, oils, hydrophobic dye molecules, capped isocyanates, polymeric co-stabilizers, and combinations thereof. 
     
     
         15 . A process as in  claim 10 , further comprising forming the polyester resin at a temperature of from about 20° C. to about 90° C. for a period of time of from about 1 minute to about 24 hours. 
     
     
         16 . A process as in  claim 1 , wherein the cold pressure fusing occurs by applying the toner particles to a substrate and fixing them to the substrate at a temperature of from about 20° C. to about 50° C., wherein the toner particles remain fixed to a substrate. 
     
     
         17 . A printing apparatus comprising:
 a toner source; and   a fuser comprising a fuser roll member capable of applying pressure of from about 3 kpsi to about 10 kpsi thereby fixing the toner onto an image receiving substrate at a temperature of from about 10° C. to about 80° C.,   wherein the toner comprises at least one amorphous polyester resin, an optional colorant, an optional wax, and at least one crystalline polyester resin, the at least one crystalline polyester resin formed by contacting at least one component selected from the group consisting of lactones, lactides, cyclic anhydrides, cyclic carbonates, and combinations thereof, with an enzyme selected from the group consisting of lipases, cutinases, and combinations thereof.   
     
     
         18 . An apparatus as in  claim 17 , wherein the toner particles remain fixed to a substrate and do not smear at pressures of from about 3 psi to about 11 psi. 
     
     
         19 . An apparatus as in  claim 17 , wherein the toner particles further comprise a shell resin. 
     
     
         20 . An apparatus as in  claim 17 , wherein the toner particles have a volume average diameter of from about 3 microns to about 25 microns, a Geometric Size Distribution of from about 1.05 to about 1.55, and a circularity of from about 0.9 to about 0.99.