BIO-BASED AMORPHOUS POLYESTER RESINS FOR EMULSION AGGREGATION TONERS
First Claim
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1. A method of making an amorphous polyester resin, the method comprising:
- synthesizing isosorbide from D-glucose;
obtaining at least one diacid selected from the group consisting of;
succinic acid obtained by a submerged culture anaerobic fermentation process, andazelaic acid produced by oxidative cleavage of oleic acid with chromic acid or by ozonolysis; and
polycondensing the isosorbide synthesized from D-glucose with the succinic acid, the azelaic acid, or a mixture of the succinic acid and the azelaic acid in the presence of a catalyst to obtain the amorphous polyester resin.
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Abstract
Disclosed are amorphous polyesters that contain only renewable resources designed for emulsion aggregation toner fabrication. The amorphous polyesters may be obtained from the mixture of three different monomers: 1,4:3,6-dianhydro-D-sorbitol (isosorbide), nonanedioic acid (azelaic acid), and butanedioic acid (succinic acid). Different polymer properties may be achieved depending on the ratio of these three monomers. By altering the ratio, polymers of high to low acid value can be obtained, as well as different ranges of glass transition temperatures.
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Citations
20 Claims
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1. A method of making an amorphous polyester resin, the method comprising:
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synthesizing isosorbide from D-glucose; obtaining at least one diacid selected from the group consisting of; succinic acid obtained by a submerged culture anaerobic fermentation process, and azelaic acid produced by oxidative cleavage of oleic acid with chromic acid or by ozonolysis; and polycondensing the isosorbide synthesized from D-glucose with the succinic acid, the azelaic acid, or a mixture of the succinic acid and the azelaic acid in the presence of a catalyst to obtain the amorphous polyester resin. - View Dependent Claims (2, 3, 4, 5, 6)
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7. A method of forming toner particles, the method comprising:
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forming a slurry by mixing together; an emulsion containing an amorphous polyester resin obtained from a method comprising; synthesizing isosorbide from D-glucose; obtaining at least one diacid selected from the group consisting of; succinic acid obtained by a submerged culture anaerobic fermentation process, and azelaic acid produced by oxidative cleavage of oleic acid with chromic acid or by ozonolysis; and polycondensing the isosorbide synthesized from D-glucose with the succinic acid, the azelaic acid, or a mixture of the succinic acid and the azelaic acid in the presence of a catalyst to obtain the amorphous polyester resin; optionally a wax; optionally a colorant; optionally a surfactant; optional a coagulant; and one or more additional optional additives; heating the slurry to form aggregated particles in the slurry; freezing aggregation of the particles by adjusting the pH; and heating the aggregated particles in the slurry to coalesce the particles into toner particles. - View Dependent Claims (8, 9, 10, 11, 12, 13, 14)
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15. Toner particles, comprising:
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an amorphous polyester resin that is the polycondensation product of isosorbide with at least one diacid selected from the group consisting of succinic acid and azelaic acid; an optional colorant, and an optional wax. - View Dependent Claims (16, 17, 18, 19, 20)
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Specification