MX2014012522A

MX2014012522A - Hybrid emulsion aggregate toner.

Info

Publication number: MX2014012522A
Application number: MX2014012522A
Authority: MX
Inventors: Guerino G Sacripante; Richard P N Veregin; Edward G Zwartz; Kimberly D Nosella; David J W Lawton
Original assignee: Xerox Corp
Priority date: 2014-01-22
Filing date: 2014-10-16
Publication date: 2015-07-21
Also published as: DE102014220718A1; DE102014220718A8; JP2015138265A; BR102014025050A2; JP6293635B2; CA2867713A1; CA2867713C; DE102014220718B4

Abstract

Toners and processes useful in providing toners suitable for electrophotographic apparatuses, including apparatuses such as digital, image-on-image, and similar apparatuses. In particular, emulsion aggregate toner compositions that use two different emulsion aggregation (EA) technologies and which comprise a base resin composed of both styrene-acrylate and polyester resins. These toner compositions further include polyaluminum chloride (PAC) instead of the more commonly used aluminum sulfate as the flocculant or aggregating agent.

Description

ORGANIC PIGMENT OF AGGREGATE OF HYBRID EMULSION Field of the Invention The present description relates to organic pigments and processes useful in the supply of organic pigments suitable for electrophotographic apparatuses, which include apparatuses such as digital apparatus, image on image and the like. In particular, the description relates to organic pigment compositions of aggregate by emulsion using two different types of emulsion aggregation (EA). Specifically, the present embodiments provide an organic emulsion aggregation pigment comprising a base resin consisting of both resins, styrene-acrylate and polyester. These embodiments comprise polyaluminium chloride (PAC) instead of the more commonly used aluminum sulfate as the flocculating or aggregation agent. The organic pigments made in this way have an improved surface morphology and provide an improved organic pigment block and percentage of heat cohesion, in particular for black organic pigment. In addition, organic pigment aggregation by hybrid emulsion compositions are lower cost and still maintain desirable developer properties such as minimum melting temperature Ref.250324 (MFT, for its acronym in English) low and minor dielectric loss.

Background of the Invention Numerous processes are within the scope of those experts in the field for the preparation of organic pigments. Emulsion aggregation is one of these methods. These organic pigments are within the scope of those skilled in the art and the organic pigments can be formed by the aggregation of a dye with a latex polymer formed by emulsion polymerization. For example, U.S. Patent No. 5,853,943, the disclosure of which is incorporated by reference in its entirety, relates to a semicontinuous emulsion polymerization process for preparing a latex by first forming a seed polymer. Other examples of emulsification / aggregation / coalescence processes for the preparation of organic pigments are illustrated in U.S. Patent Nos. 5,403,693; 5,418,108; 5,364,729 and 5,346,797, the description of each of which is incorporated herein by reference in its entirety. Other processes are described in U.S. Patent Nos. 5,527,658; 5,585,215; 5,650,255; 5,650,256 and 5,501,935, the description of each of which is incorporated herein by reference in its entirety.

Electrophotography, which is a method for displaying image information by forming an electrostatic image is currently used in various fields. The term "electrostatic" is generally used interchangeably with the term "electrophotographic". In general, the electrophotography comprises the formation of an electrostatic latent image on a photoreceptor, followed by the development of the image with a developer containing an organic pigment and subsequent transfer of the image onto the transfer material such as paper or a sheet, and fixing the image on the transfer material by using heat, a solvent, pressure and / or the like to obtain a permanent image.

Organic emulsion aggregation pigments may comprise various resins for use in latex formation. One type of organic emulsion aggregation pigment provides high gloss and uses styrene-acrylate, a lower cost resin. Another type of organic emulsion aggregation pigment provides better melt performance (eg minimum fixation temperature (MFT) of less than about 20 ° C) and uses polyesters as the base resin. However, the polyester resins used are expensive. In this way, the present modalities seek form an organic aggregation pigment by hybrid emulsion that combines the advantages of both types of organic pigments. However, it has been discovered that organic pigments with styrene-acrylate latexes do not melt at the same temperature during the organic pigment process as organic polyester pigments, which generates variations in the surface morphology in a hybrid of the Two types of organic pigment (more polystyrene / acrylate remains on the surface). The present embodiments replace part of the polyester resin used in the core of the lower melting organic pigment with part of the styrene-acrylate of the high gloss organic pigment and include PAC as the aggregation agent. This hybrid composition provides an organic pigment with a lower cost that retains a good fusion performance and a low dielectric loss. In addition, the PAC unexpectedly improves the surface morphology by reducing the amount of styrene-acrylate on the surface.

Summary of the Invention The present embodiments provide an organic pigment composition comprising: organic pigment particles having a core, wherein the core comprises a resin, a dye, a wax and polyaluminum chloride, wherein the resin comprises a styrene-acrylate resin , a crystalline polyester resin and a amorphous polyester resin; and a cover placed on the core.

In specific embodiments, an organic pigment composition is provided with a developer comprising: an organic pigment composition; and an organic pigment carrier, wherein the organic pigment composition comprises organic pigment particles having a core, wherein the core comprises a resin, a dye, a wax and polyaluminum chloride, wherein the resin comprises a resin of styrene-acrylate, a crystalline polyester resin and an amorphous polyester resin and a cover placed on the core.

In still further embodiments, a developer is provided comprising a method for making an organic pigment comprising bonding by mixing and emulsifying a resin, a colorant and a wax, wherein the resin comprises a styrene-acrylate resin, a polyester resin crystalline to form a latex emulsion; add polyaluminium chloride to the latex emulsion; adding the latex emulsion to form the cores of the organic pigment particles, wherein the organic pigment particle cores comprise the styrene-acrylate resin, the crystalline polyester resin and the amorphous polyester; form a cover over the particle cores of organic pigment to form the pigment particles organic; coalesce the organic pigment particles; and cooling the organic pigment particles.

Brief Description of the Figures For a better understanding of the present modalities, reference may be made to the appended figures.

Figure 1A provides scanning electron microscopy (SEM) images of organic pigment particles based on comparative polyester; Figure IB shows SEM images of a hybrid organic pigment made in accordance with the present embodiments; Figure 1C provides SEM images of another hybrid organic pigment made according to the present embodiments; Y Figure 2 is a graph illustrating the improved heat cohesion percent of the organic pigment made according to the present embodiments as compared to control organic pigments.

Detailed description of the invention As described above, the present embodiments provide organic hybrid emulsion aggregation (EA) pigment in which a conventional polyester particle core is replaced with a portion of a styrene-acrylate resin. This Thus, the novel organic pigment composition has styrene-acrylate and its core as well as crystalline and amorphous polyester resins in the core. These resins are used to form the latex emulsion and are finally incorporated into the core of the resulting particle. The organic pigment particle cover comprises polyester resin and, specifically, crystalline polyester resin. The styrene-acrylate resin is a resin of a lower cost compared to a polyester resin used and therefore reduces the total cost of organic pigment processing but at the same time obtains a good melting performance, dielectric loss, charged , blockage and percent cohesion. In addition, the present organic pigment embodiments include polyaluminium chloride (PAC) as the aggregation agent. It has been discovered that PAC unexpectedly improves surface morphology by reducing the amount of styrene-acrylate on the surface.

In embodiments, the styrene-acrylate resin is present in the core of the organic pigment particle in an amount of from about 5 to about 35, or from about 10 to about 35, or from about 20 to about 35 weight percent of the total weight of the core. In modalities, the particle size of the emulsion of styrene-acrylate is from about 100 nm to about 160 nm, or from about 100 nm to about 140 nm. It has been found that the use of the styrene-acrylate resin in this range together with PAC provides optimum results in organic EA pigment with good performance and properties and improved surface morphology.

In embodiments, the resins can be a polyester resin such as an amorphous resin, a crystalline resin and / or a combination thereof, which includes the resins described in U.S. Patents. 6,593,049 and 6,756,176, the description of each of which is incorporated herein by reference in its entirety. Suitable resins may also include a mixture of an amorphous polyester resin and a crystalline polyester resin as described in U.S. Patent No. 6,830,860, the disclosure of which is incorporated herein by reference in its entirety.

In embodiments, the crystalline polyester resins are present in the core of the organic pigment particle in an amount of from about 1 to about 20, or from about 1 to about 15, or from about 3 to about 10 weight percent of the weight total of the core. In modalities, the crystalline polyester resin used in the core is selected from the group consisting of poly (ethylene-adipate), poly (propylene-adipate), poly (butylene-adipate), poly (pentylene-adipate), poly (hexylene-adipate), poly (octylene) -adipate), poly (ethylene-succinate), poly (propylene-succinate), poly (butylene-succinate), poly- (pentylene-succinate, poly (hexylene-succinate), poly- (octylene-succinate), poly (ethylene) -sebacate), poly (propylene-sebacate), poly (butylene-sebacate), poly (pentylene-sebacate), poly (hexylene-sebacate), poly (octylene-sebacate), poly- (decylene-sebacate), poly (decylene) -decanoate), poly (ethylene-decanoate), poly (ethylene-dodecanoate), poly (nonylene-sebacate), poly (nonylene-decanoate), copoly (ethylene-fumarate) -poly (ethylene-sebacate), copoly (ethylene- fumarate) -copoly (ethylene-decanoate), copoly (ethylene-fumarate) -copoly (ethylene-dodecanoate) to further reduce costs The preferred low cost crystalline polyesters are (1,9-nonylene-l, 12- dodecanoate), poly (1,6-hexylene-1,12-dodecanoate) ) and poly (1,6-hexylene-l, 10-decanoate).

In embodiments, the amorphous polyester resin is present in the organic pigment particle core in an amount of from about 20 to about 80, or from about 20 to about 70, from about 30 to about 65 weight percent of the core weight. . The amorphous polyester resins are selected from the group consisting of poly (bisphenol-A) alkoxylated co-fumarate-co-terephthalate-dodecenyl co-succinate) and mixtures thereof. In embodiments, as indicated above, an unsaturated amorphous polyester resin can be used as a latex resin. In embodiments, the amorphous polyester resin can be obtained from Kao Corporation as FXC42 and FXC56. Examples of these resins include the resins in U.S. Patent Nos. 6,063,827 and No, 466,254, the description of each of which is incorporated herein by reference in its entirety. Exemplary unsaturated amorphous polyester resins include, but are not limited to poly (co-fumarate propoxylated bisphenol), poly (co-fumarate ethoxylated bisphenol), poly (butyl-butylated co-fumarate bisphenol), poly (co-propoxylated bisphenol co-bisphenol) ethoxylated co-fumarate), poly (1,2-propylene fumarate), poly (propoxylated bisphenol co-maleate), poly (bisphenol ethoxylated co-maleate), poly (bisphenol butyloxylated co-maleate), poly (propoxylated co-bisphenol) ethoxylated co-bisphenol co-maleate), poly (1,2-propylene maleate), poly (propoxylated co-itaconate bisphenol), poly (co-itaconate ethoxylated bisphenol), poly (butyloxylated co-itaconate bisphenol), poly (co- -propoxylated bisphenol co-bisphenol ethoxylated co-itaconate), poly (itaconate of 1,2-propylene), poly (co-bisphenol propoxylated co-bisphenol ethoxylated co-fumarate-co-terephthalate-dodecenyl co-succinate) and combinations of the same.

The organic emulsion aggregation pigment of the present embodiments has a minimum melting temperature (MFT) of from about 90 to about 150, or from about 100 to about 130, or from about 100 to about 125. This it is from about 15 to about 20 less than other organic aggregation pigments by non-polyester emulsion in the core or the shell. The present embodiments also have acceptable dielectric loss from about 10 to about 40, or from about 20 to about 40, or from about 20 to about 35. From previous studies, the present inventors discovered that the dielectric losses of organic pigments can be improve by increasing the thickness of the roof and by decreasing the coalescence temperature. In this manner, the present organic pigment composition preferably has a percent cover from about 28 to about 40, or from about 30 to about 38, or from about 30 to about 36 percent of the organic pigment particles. In making these organic pigment compositions, the coalescence temperature used is preferably from about 70 to about 90 ° C, from about 70 to about 80 ° C, or from about 70 to about 77 ° C. In particular embodiments, the latex particle size used in making these organic pigment compositions is from about 100 nm to 159 nm. The present inventors have also discovered that by decreasing the coalescence temperature and by using smaller latex particle sizes they help to avoid any phase separation of the styrene-acrylate resin from the polyester resins and maintain the styrene-acrylate in the core instead of moving to the surface. In this way, good electrical and fusion properties are maintained.

LATEX RESINS In embodiments, a developer is described which includes a carrier coated with resin and an organic pigment, wherein the organic pigment may be an organic emulsion aggregation pigment containing, but not limited to a latex resin, a wax and a cover polymeric Generally, the latex resin may be comprised of a first and a second monomer compositions. Any suitable monomer or mixture of monomers can be selected to prepare the first monomer composition and the second monomer composition. The selection of monomer or mixture of monomers for The first monomeric composition is independent of the second monomeric composition and vice versa. In case a mixture of monomers is used, typically the latex polymer will be a copolymer. As described above, the latex resin is composed of at least styrene acrylate, a polyester resin and a crystalline resin.

Exemplary monomers for the first and / or the second of the monomeric compositions include, but are not limited to, polyesters, styrene, alkyl acrylate such as methyl acrylate, ethyl acrylate, butyl arylate, isobutyl acrylate, dodecyl acrylate. , n-octyl acrylate, 2-chloroethyl acrylate, b-carboxyethyl acrylate (b-CEA), phenyl acrylate, methyl alpha-chloroacrylate, methyl methacrylate, ethyl methacrylate and butyl methacrylate; butadiene; isoprene; methacrylonitrile; acrylonitrile; vinyl ethers, such as vinyl methyl ether, vinyl isobutyl ether, vinyl ethyl ether and the like; vinyl esters such as vinyl acetate, vinyl propionate, vinyl benzoate and vinyl butyrate; vinyl ketones such as vinyl methyl ketone, vinyl hexyl ketone and methyl isopropenyl ketone; vinylidene halides such as vinylidene chloride and vinylidene chlorofluoride; N-vinyl indole; N-vinyl pyrrolidone; methacrylate; acrylic acid; methacrylic acid; acrylamide; methacrylamide; vinylpyridine; Vinylpyrrolidone; dione vinyl-N-methylpyridinium chloride; vinylnaphthalene; p-chlorostyrene; vinyl chloride; vinyl bromide; vinyl fluoride; ethylene; propylene; Butylenes; isobutylene and the like and mixtures thereof.

In some embodiments, the first monomeric composition and the second monomeric composition may comprise, independently of each other, two or three or more different monomers (side note, sounds very similar to my previous entry). Therefore, the latex polymer may comprise a copolymer. Illustrative examples of latex copolymer include poly (styrene-n-butyl-p-CEA acrylate), poly (styrene-alkyl acrylate), poly (styrene-1,3-diene), poly (styrene-alkyl methacrylate) ), poly (alkyl methacrylate-alkyl acrylate), poly (alkyl methacrylate-aryl acrylate), poly (aryl methacrylate-alkyl acrylate), poly (alkyl methacrylate), poly (styrene-alkyl acrylate- acrylonitrile), poly (styrene-1,3-diene-acrylonitrile), poly (alkyl acrylate, acrylonitrile), poly (styrene-butadiene), poly (methylstyrene-butadiene), poly (methyl methacrylate-butadiene), poly ( ethyl methacrylate-butadiene), poly (propyl-butadiene methacrylate), poly (butyl-butadiene methacrylate), poly (methyl-butadiene acrylate), poly (ethyl-butadiene-acrylate), poly (propyl-butadiene-acrylate) ), poly (butyl-butadiene acrylate), poly (styrene-isoprene), poly (methylstyrene- isoprene), poly (methyl methane-isoprene), poly (ethyl-isoprene-methacrylate), poly (propyl-isoprene methacrylate), poly (butyl-isoprene methacrylate), poly (methyl-isoprene-acrylate), poly ( ethyl acrylate-isoprene), poly (propyl-isoprene acrylate), poly (butyl-isoprene acrylate); poly (styrene-propyl acrylate); poly (styrene-butyl acrylate), poly (styrene-butadiene-acrylonitrile), poly (styrene-butyl acrylate-acrylonitrile) and the like.

In embodiments, the first monomeric composition and the second monomeric composition may be substantially insoluble in water, such as hydrophobic, and may be dispersed in an aqueous phase with suitable agitation when added to a reaction vessel.

The weight ratio between the first monomeric composition and the second monomeric composition may be in the range of about 0.1: 99.9 to about 50:50, which includes from about 0.5: 99.5 to about 25:75, from about 1:99 to about 10:90.

In embodiments, the first monomeric composition and the second monomeric composition may be the same. Examples of the first / second monomer composition may be a mixture comprising styrene and alkyl acrylate, such as a mixture comprising styrene, n-acrylate and butyl and b-CEA. Based on the total weight of the monomers, styrene can be present in an amount of from about 1% to about 99%, from about 50% to about 95%, from about 70% to about 90%, although it can be present in greater or lesser amounts; the alkyl acrylate, such as n-butyl acrylate may be present in an amount of from about 1% to about 99%, from about 5% to about 50%, from about 10% to about 30%, although it may be present in greater or lesser amounts.

In embodiments, the resins can be a polyester resin formed by reacting a diol with a diacid in the presence of an optional catalyst. For formation of a crystalline polyester, suitable organic diols include aliphatic diols with from about 2 to about 36 carbon atoms, such as 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol , 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,1,10-decanediol, 1,12-dodecanediol and the like. The aliphatic diol can be selected, for example, in an amount from about 40 to about 60 mol%, in embodiments, from about 42 to about 55% in mole, in modalities, from approximately 45 to approximately 53% in mole (although quantities outside these ranges can be used).

Examples of organic diacids or diesters including vinyl diacids or vinyl diesters selected for the preparation of crystalline resins including oxalic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, 1,12- dodecanoic, fumaric acid, dimethyl fumarate, dimethyl itaconate, cis, 1,4-diacetoxy-2-butene, diethyl fumarate, diethyl maleate, italic acid, isophthalic acid, terephthalic acid, naphthalene-2,6-dicarboxylic acid , naphthalene-2,7-dicarboxylic acid, cyclohexane dicarboxylic acid, malonic acid and mesaconic acid, a diester or anhydride thereof.

The organic diacid may be selected in an amount, for example, in embodiments from about 40 to about 60 mol%, in embodiments from about 42 to about 52 mol%, in embodiments from about 45 to about 50 mol%.

The crystalline resin may possess various melting points, for example from about 30 ° C to about 120 ° C, in modalities from about 50 ° C to about 90 ° C. The crystalline resin can have an average molecular weight number (Mn), as measured by gel permeation chromatography (GPC) for example, from about 1,000 to about 50,000, in modalities, from about 2,000 to about 25,000 and an average by weight of molecular weight (Mw) of, for example, from about 2,000 to about 100,000, in embodiments, from about 3,000 to about 80,000, determined by gel permeation chromatography using polystyrene standards. The molecular weight distribution (Mw / Mn) of the crystalline resin can be, for example, from about 2 to about 6, in embodiments, from about 3 to about 4.

Examples of diacids or diesters include vinyl diacids or vinyl diesters used for the preparation of amorphous polyesters include dicarboxylic acids or diesters such as terephthalic acid, italic acid, isophthalic acid, fumaric acid, dimethyl fumarate, dimethyl itaconate, cis, 1,4-diacetoxy-2-butene, diethyl fumarate, diethyl maleate, maleic acid, succinic acid, itaconic acid, succinic acid, succinic anhydride, dodecyl succinic acid, dodecyl succinic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid , suberic acid, azelaic acid, diacid dodecane, dimethyl terephthalate, terephthalate diethyl, dimethyl isophthalate, diethyl isophthalate, dimethyl phthalate, phthalic anhydride, diethyl phthalate, dimethyl succinate, dimethyl fumarate, dimethyl maleate, dimethyl glutarate, dimethyl adipate, dimethyl dodecyl succinate and combinations thereof.

The organic diacid or diester may be present, for example, in an amount of about 40 to about 60 mol% of the resin, in embodiments, from about 42 to about 52 mol percent of the resin, in embodiments, from about 45. up to about 50 mole percent of the resin. Examples of the alkylene oxide adducts of bisphenol include polyoxypropylene (2.2) -2,2-bis (4-hydroxyphenyl) propane, polyoxypropylene (3.3) -2,2-bis (4-hydroxyphenyl) propane, polyoxyethylene (2.0) -2,2-bis (4-hydroxyphenyl) propane, polyoxyethylene (2.2) -2, -bis (4-hydroxyphenyl) propane, polyoxypropylene (2.0) -polyoxyethylene- (2.0) -2,2-bis (4-hydroxyphenyl) propane and polyoxypropylene (6) -2,2-bis (4-hydroxyphenyl) propane. These compounds can be used alone or as a combination of two or more thereof.

Examples of additional diols which can be used in the generation of amorphous polyester include 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, pentanediol, hexanediol. , 2,2- dimethylpropanediol, 2,2,3-trimethylhexanediol, heptanediol, dodecanediol, 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, xylenediimethanol, cyclohexanediol, diethylene glycol, dipropylene glycol, dibutylene and combinations thereof. The amount of organic diol selected may vary and may be present, for example, in an amount from about 40 to about 60 mole percent of the resin, in embodiments from about 42 to about 55 mole percent of the resin, in embodiments from about 45 to about 53 mole percent of the resin.

Polycondensation catalysts which can be used in the formation of either the crystalline or amorphous polyesters include tetraalkyl titanates, dialkyltin oxide such as dibutyltin oxide, tetraalkyltins such as dibutyltin dilaurate and dialkyltin oxide hydroxides such as hydroxyl hydroxide. butyltin oxide, aluminum alkoxides, alkyl zinc, dialkyl zinc, zinc oxide, stannous oxide, or combinations thereof. These catalysts can be used in amounts, for example, from about 0.01 mole percent to about 5 mole percent based on the initial diacid or diester used to generate the polyester resin.

In addition, in embodiments, a crystalline polyester resin may be contained in the binding resin. The crystalline polyester resin can be synthesized from an acid component (dicarboxylic acid) and an alcohol component (diol). In the following, the term "acid-derived component" denotes a constitutive portion that is originally an acidic component prior to the synthesis of a polyester resin and an "alcohol-derived component" indicates a constitutive portion that was originally an alcohol component. before the synthesis of the polyester resin.

A "crystalline polyester resin" indicates that which does not show a variation in the endothermic amount gradually but an endothermic peak evident in differential scanning calorimetry (DSC). However, a polymer obtained by copolymerizing the crystalline polyester backbone and at least one other component is also called a crystalline polyester and the amount of the other component is 50% by weight or less.

As the acid derivative component, an aliphatic dicarboxylic acid such as a straight chain carboxylic acid can be used. Examples of straight chain carboxylic acids include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid. acid sebacic acid, 1, 9-nonane dicarboxylic acid, 1,10-decanedicarboxylic acid, 1,1-undecanedicarboxylic acid, 1,12-dodecanedicarboxylic acid, 1,13-tridecanedicarboxylic acid, 1,14-tetradecanedicarboxylic acid, acid 1, 16- hexanedicarboxylic acid and 1,18-octadecanedicarboxylic acid as well as lower alkyl esters and acid anhydrides thereof. Among these, acids having 6 to 10 carbon atoms may be desirable to obtain a suitable melting point and glass loading properties. In order to improve the crystallinity, the straight chain carboxylic acid may be present in an amount of about 95 mol% or greater of the acid component and, in embodiments, more than about 98 mol% of the acid component. Other acids are not particularly restricted, and examples thereof include conventionally known divalent carboxylic acids and dihydric alcohols, for example those described in "Polymer Data Handbook: Basic Edition" (Soc. Polymer Science, Japan Ed .: Baihukan). Specific examples of the monomeric components include, such as divalent carboxylic acids, dibasic acids such as italic acid, isophthalic acid, terephthalic acid, naphthalene-2,6-dicarboxylic acid, naphthalene-2,7-dicarboxylic acid and cyclohexanedicarboxylic acid and anhydrides and lower alkyl esters thereof as well as combinations of the same and similar.

As the alcohol component, aliphatic dialcohols can be used. Examples thereof include ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-dekanediol, 1,11-dodecanediol, 1,12-undecanediol, 1,13-tridecanediol, 1,14-tetradecanediol, 1,18-octadecanediol and 1,20-eicosanediol. Among these, those having from about 6 to about 10 carbon atoms can be used to obtain desirable melting points and crystal loading properties. In order to increase the crystallinity, it may be useful to use linear chain dialcoholes in an amount of about 95 mol% or greater, in embodiments, about 98 mol% or greater.

Examples of other dihydric dialcohols which may be used include bisphenol A, hydrogenated bisphenol A, adduct of bisphenol A-ethylene oxide, adduct of bisphenol A-propylene oxide, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, diethylene glycol , propylene glycol, dipropylene glycol, 1,3-butanediol, neopentyl glycol, combinations thereof and the like.

To adjust the acid number and the hydroxyl number, the following can be used: monovalent acids such as acetic acid and benzoic acid; monohydric alcohols such as cyclohexanol and benzyl alcohol; benzenecarboxylic acid, naphthalene tricarboxylic acid and anhydrides and lower alkyl esters thereof; trivalent alcohols such as glycerin, trimethylolethane, trimethylolpropane, pentaerythritol, combinations thereof and the like.

The crystalline polyester resins can be synthesized from a combination of components that are selected from the aforementioned monomeric components, by the use of conventional known methods. Exemplary methods include the ester exchange method and the direct polycondensation method, which can be used singly or in a combination thereof. The molar ratio (acid component / alcohol component) when the acid component and the alcohol component are reacted, can vary based on the reaction conditions. The molar ratio is usually about 1/1 in direct polycondensation. In the ester exchange method, a monomer such as ethylene glycol, neopentyl glycol or cyclohexanedimethanol, which can be removed by distillation under vacuum, can be used in excess.

SURFACTANTS Any suitable surfactant can be used for the preparation of latex and wax dispersions, according to the present description. Depending on the emulsion system, any desired nonionic or ionic surfactant may be contemplated, such as an anionic or cationic surfactant.

Examples of suitable anionic surfactants include, but are not limited to sodium dodecylsulfate, sodium dodecylbenzenesulfonate, sodium dodecyl naphthalenesulfate, dialkylbenzenealkyl sulfates, nitric acid, NEOGEN RMR and NEOGEN SC1®, available from Kao, Tayca PowerMR, available from Tayca Corp., DOWFAXMR, available from Dow Chemical Co .; and the like, as well as mixtures thereof. The anionic surfactants can be used in any desired or effective amount, for example, at least about 0.01% by weight of the total monomers used to prepare the latex polymer, at least about 0.1% by weight of the total monomers used for preparing the latex polymer. prepare the latex polymer; and not more than about 10% by weight of the total monomers used to prepare the latex polymer, not more than about 5% by weight of the total monomers used to prepare the latex polymer, although the amount may be outside these ranges .

Examples of suitable cationic surfactants include, but are not limited to, dialkylbenzealkylammonium chloride, lauryltrimethylammonium chloride, alkylbenzylmethylammonium chloride, alkylbenzyldimethylammonium bromide, benzalkonium chloride, cetylpyridinium bromide, trimethylammonium bromides of 12, 15 and 17 carbons, quaternized polyoxyethylalkylamino halide salts, dodecylbenzyltriethylammonium chloride, MIRAP0LMR and ALKAQUAT ™ (available from Alkaril Chemical Company), SANIZOL ™ (benzalkonium chloride, available from Kao Chemical) and the like as well as mixtures thereof.

Examples of suitable nonionic surfactants include, but are not limited to polyvinyl alcohol, polyacrylic acid, metallose, methylcellulose, ethylcellulose, propylcellulose, hydroxyethylcellulose, carboxymethylcellulose, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene octyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene monolaurate. sorbitan, polyoxyethylene stearyl ether, polyoxyethylene-nonylphenyl ether, dialkylphenoxypoly (ethyleneoxy) -ethanol (available from Rhone Poulenc as IGEPAL CA 210MR, IGEPAL CA 520MR, IGEPAL CA 720MR, IGEPAL CO 890MR, IGEPAL CO 720MR, IGEPAL CO 290MR, IGEPAL CA 210MR, ANTAROX 890MR and ANTAROX 897MR) and the like, as well as mixtures thereof.

INITIATORS Any suitable initiator or mixture of initiators can be selected in the latex processes and in the organic pigment processes. In modalities, the initiator is selected from known free radical polymerization initiators. The free radical initiator can be any free radical polymerization initiator capable of initiating a free radical polymerization process and mixtures thereof, such as a free radical initiator that is capable of providing free radical species by heating to a upper temperature of about 30 ° C.

Although water-soluble free radical initiators are used in emulsion polymerization reactions, other free radical initiators can also be used. Examples of suitable initiators for free radicals include, but are not limited to peroxides such as ammonium persulfate, hydrogen peroxide, acetyl peroxide, cumyl peroxide, tertbutyl peroxide, propionyl peroxide, benzoyl peroxide, chlorobenzoyl peroxide, dichlorobenzoyl peroxide, bromomethylbenzoyl peroxide, lauroyl peroxide, diisopropyl peroxycarbonate, tetralin hydroperoxide, l-phenyl-2-methylpropyl 1-hydroperoxide and tert-butyl hydroperoxide; pertriphenyl acetate, tertiary butyl acetate; terbutyl peracetate; Terbutyl perbenzoate; terbutyl perfenylacetate; Terbutyl permetoxyacetate; per-N- (3-toluyl) tert-butyl carbamate; sodium persulfate; potassium persulfate; azo compounds such as 2,2'- azobispropane, 2,21-dichloro-2,21-azobispropane, 1,1'-azo diacetate (methylethyl), 2,2'-azobis (2-amidinopropane) hydrochloride, 2,21-azobis (2-) nitrate amidinopropane), 2,2'-azobisisobutane, 2,2'-azobisisobutylamide, 2,2'-azobisisobutyronitrile, 2,2'-azobis-2-methylpropionate methyl, 2,2'-dichloro-2,2'-azobisbutane , 2, 2'-azobis-2-methylbutyronitrile, dimethyl 2,2'-azobis-isobutyrate, sodium 1,1'-azobis (sodium-1-methylbutyronitrile-3-sulfonate), 2- (4-methylphenylazole) ) -2-metilmalonodinitrilo, 4,4'-azobis acid-cyanovaleric-4, 3, 5-dihidroximetilfenilazo-2-metilmalonodinitrilo, 2- (4-bromofenilazo) -2-alilmalonodinitrilo, 2,2'-azobis-2-methylvaleronitrile , Dimethyl 4,4'-azobis-4-cianovalerate, 2,2'-azobis-2,4-dimethylvaleronitrile, 1,1'-azobis-cyclohexanonitrile, 2,2'-azobis-2-propylbutyronitrile, 1,1 azobis-1-clorofeniletano, 1,1'-azobis-1-cyclohexanecarbonitrile, 1,1'-azobis-1-cicloheptanonitrilo, 1,1'-azobis-l-phenylethane, 1,1'-azobiscumeno, 4- nitrophenylazobenzylcyanoacetate Tato ethyl fenilazodifenilmetano, fenilazotrifenilmetano, 4-nitrofenilazotrifenilmetano, 1'-azobis-1,2-diphenylethane, poly (bisphenol A-4,4'-azobis-4-cyanopentanoate) and poly (tetraethylene glycol-2,2'- azobisisobutyrate); 1,4-bis (pentaethylene) -2-tetrazene; 1,4-dimethoxycarbonyl-1,4-diphenyl-2-tetrazene and the like; and mixtures thereof.

The most typical free radical initiators include, but are not limited to ammonium persulfate, hydrogen peroxide, peroxide, acetyl peroxide, cumyl peroxide tertbutyl peroxide, propionyl peroxide, benzoyl peroxide, chlorobenzoyl peroxide, dichlorobenzoyl peroxide bromometilbenzoilo, lauroyl peroxide , sodium persulfate, potassium persulfate, diisopropyl peroxycarbonate and the like.

Based on the total weight of the monomers to be polymerized, the initiator can be present in an amount from about 0.1% to about 5%, from about 0.4% to about 4%, from about 0.5% to about 3%, although it may be present in larger or smaller amounts.

A chain transfer agent can optionally be used to control the degree of polymerization of the latex and thus control the molecular weight and molecular weight distribution of the latexes from the latex process and / or the organic pigment process of the latex process. according to the present description. As can be seen, a chain transfer agent can become part of the latex polymer.

CHAIN TRANSFER AGENT In embodiments, the chain transfer agent has a carbon-sulfur covalent bond. The carbon-sulfur covalent bond has an absorption peak in the region of the wave number that varies from 500 to 800 enr1 in the infrared absorption spectrum. When the chain transfer agent is incorporated in the latex and the organic pigment is made from the latex, the absorption peak can be changed, for example, to a region of the wave number from 400 to 4000 cnr1.

Agents chain transfer specimens include, but are not limited to n-alkyl mercaptans from 3 to 15 carbon atoms such as n-propyl mercaptan, n-butyl mercaptan, n-amyl mercaptan, n-hexyl, n-heptilmercaptano, n-octyl, n-nonylmercaptan, n-decylmercaptan and n-dodecyl mercaptan; branched alkyl mercaptans such as isopropyl mercaptan, isobutilmercaptano, s-butyl mercaptan, terbutilmercaptano, cyclohexylmercaptan, tert-hexadecylmercaptan, tert-lauryl mercaptan, tert-nonilmercaptano, tert-octyl mercaptan and tert-tetradecyl; mercaptans containing aromatic ring, such as allyl mercaptan, 3-phenylpropyl mercaptan, phenyl mercaptan and mercaptotriphenyl methane; etc. The terms mercaptan and thiol can be used interchangeably to indicate a C-SH group.

Examples of chain transfer agents also include, but are not limited to, dodecanethiol, butanethiol, isooctyl 3-mercaptopropionate, 2-methyl-5- terbutylthiophenol, carbon tetrachloride, carbon tetrabromide and the like.

Based on the total weight of the monomers to be polymerized, the chain transfer agent can be present in an amount from about 0.1% to about 7%, from about 0.5% to about 6%, from about 1.0% up to about approximately 5%, although they may be present in greater or lesser amounts.

In embodiments, a branching agent can optionally be included in the first / second monomeric composition to control the branching structure of the target latex. Exemplary branching agents include, but are not limited to, diacanodiol diacrylate (ADOD), trimethylpropane, pentaerythritol, trimellitic acid, pyromellitic acid, and mixtures thereof.

Based on the total weight of the monomers to be polymerized, the branching agent can be present in an amount from about 0% to about 2%, from about 0.05% to about 1.0%, from about 0.1% to about 0.8. %, although it may be present in larger or smaller amounts.

In the latex process and the organic pigment process of the description, the emulsification can be perform by any suitable process such as mixing at elevated temperature. For example, the emulsion mixture can be mixed in a homogenizer which is adjusted from about 200 to about 400 rpm and at a temperature from about 40 ° C to about 80 ° C for a period from about 1 minute to about 20 minutes.

Any type of reactor can be used without restriction. The reactor may include means for agitating the compositions therein, such as an impeller. A reactor may include at least one impeller. For the formation of the latex and / or the organic pigment, the reactor can be operated during the process so that the impellers can operate at an effective mixing speed of about 10 to about 1,000 rpm.

After completing the monomer addition, the latex can be allowed to stabilize by maintaining the conditions for a period of time, for example, for about 10 to about 300 minutes before cooling. Optionally, the latex formed by the above process can be isolated by standard methods known in the art, for example, coagulation, dissolution and precipitation, filtering, washing, drying or the like.

The latex of the present disclosure can be selected for emulsion-aggregation-coalescence processes for the formation of organic pigments, inks and developers by known methods. The latex of the present disclosure can be combined melted or otherwise mixed with various organic pigment ingredients such as a wax dispersion, a coagulant, an optional silica, an optional charge improver additive or charge control additive, a optional surfactant, an optional emulsifier, an optional flow additive and the like. Optionally, the latex (eg, about 40% solids) can be diluted to the desired solids loading (eg, about 12 to about 15% by weight solids) before being formulated into an organic pigment composition.

Based on the total weight, the latex may be present in an amount of from about 50% to about 100%, from about 60% to about 98%, from about 70% to about 95%, although it may be present in larger amounts or minors The methods for producing these latex resins can be carried out as described in the description of U.S. Patent No. 7,524,602, incorporated herein by reference in its entirety.

COLORING Various suitable suitable dyes, such as dyes, pigments, can be included in the organic pigment. mixtures of dyes, mixtures of pigments, mixtures of dyes and pigments and the like. The colorant may be included in the organic pigment in an amount, for example, from about 0.1 to about 35% by weight of the organic pigment, from about 1 to about 15% by weight of the organic pigment, from about 3 to about 10% by weight. organic pigment weight although quantities outside these ranges can be used.

As examples of suitable colorants, mention may be made of carbon black such as REGAL 330MR; magnetites such as Mobay magnetite M08029MR and M08060MR; Columbian magnetites; surface treated magnetites MAPICO BLACKSMR; Pfizer magnetite, CB4799MR, CB5300MR, CB5600MR, and MCX6369MR; Bayer magnetite, BAYFERROX 8600MR and 8610MR; magnetites of Northern pigments, NP604MR and NP-608MR; Magnox TMB-100MR or TMB104MR magnetites; and similar. As colored pigments, cyan, magenta, yellow, red, green, brown, blue or mixtures thereof can be selected. Generally pigments or cyan, magenta or yellow dyes or mixtures thereof are used. The pigment or pigments may be water-based pigment dispersions.

Specific examples of pigments include SUNSPERSE 6000, FLEXIVERSE and AQUATONE as dispersions of water-based pigments from SUN Chemicals, HELIOGEN BLUE L6900MR, D6840MR, D7080MR, D7020MR, PYLAM OIL BLUEMR, PYLAM OIL YELLOWMR, PIGMENT BLUE IMR, available from Paul Uhlich & Company, Inc .; PIGMENT VIOLET 1MR PIGMENT RED 48MR, LEMON CHROME YELLOW DCC 1026MR, E.D. TOLUIDINE REDMR and BON RED CMR available from Dominion Color Corporation, Ltd., Toronto, Ontario; NOVAPERM YELLOW FGLMR, HOSTAPERM PINK EMR from Hoechst; CINQUASIA MAGENTAMR, available from E. I. DuPont de Nemours & Co. , and similar. The colorants that can be selected are black, cyan, magenta, yellow and mixtures thereof. Examples of magentas are substituted quinacridone and anthraquinone 2,9-dimethyl dyes identified in the Index color as CI60710, CI Dispersed Red 15, diazo dye identified in the Color Index as CI26050, CI Solvent Network 19 and the like. Illustrative examples of cyan colors include tetra (octadecylsulfonamido) phthalocyanine copper, copper phthalocyanine pigment x listed in the Color Index as CI74160, CI Pigment Blue, Pigment Blue 15: 3, Anthratrene Blue, identified in the Color Index as CI 69810, Special Blue X 2137 and the like. Illustrative examples of yellows are yellow diarylide 3,3 'dichlorobenzidene acetoacetanilides, a monoazo pigment identified in the Color Index as CI12700, CI Solvent Yellow 16, a nitrophenylamine sulfonamide identified in the Color Index as Foron Yellow SE / GLN, CI Dispersed Yellow 33 , 2,5-dimethoxy-4-sulfonanilide phenylazo 4'-chloro-2,5-dimethoxy acetoacetanilide and Permanent Yellow FGL. The magnetites colored ones such as mixtures of MAPICO BLACKMR and cyan components can also be selected as colorants. Other known colorants that can be selected such as Levanyl Black-ASF (Miles, Bayer) and Sunsperse Coal Black LHD 9303 (Sun Chemicals), and colored dyes such as Neopen Blue (BASF), Sudan Blue OS (BASF), PV Fast Blue B2G01 (American Hoechst), Sunsperse Blue BHD 6000 (Sun Chemicals), Irgalite Blue BCA (CibaGeigy), Paliogen Blue 6470 (BASF), Sudan III (Matheson, Coleman, Bell), Sudan II (Matheson, Coleman, Bell), Sudan IV (Matheson, Coleman, Bell), Sudan Orange G (Aldrich), Sudan Orange 220 (BASF), Paliogen Orange 3040 (BASF), Ortho Orange OR 2673 (Paul Uhlich), Paliogen Yellow 152, 1560 (BASF), Lithol Fast Yellow 0991K (BASF), Paliotol Yellow 1840 (BASF), Neopen Yellow (BASF), Novoperm Yellow FG1 (Hoechst), Permanent Yellow YE 0305 (Paul Uhlich); Lumogen Yellow D0790 (BASF), Sunsperse Yellow YHD 6001 (Sun Chemicals); Suco Gelb L1250 (BASF), Suco Yellow D1355 (BASF), Hostaperm Pink E (American Hoechst), Fanal Pink D4830 (BASF), Cinquasia Magenta (DuPont); Lithol Scarlet D3700 (BASF), Toluidine Red (Aldrich), Scarlet for Thermoplast NSD PS PA (Ugine Kuhlmann of Canada), ED Toluidine Red (Aldrich), Lithol Rubine Toner (Paul Uhlich), Lithol Scarlet 4440 (BASF), Bon Red C (Dominion Color Company), Royal Brilliant Red RD 8192 (Paul Uhlich), Oracet Pink RF (Ciba-Geigy), Paliogen Red 3871K (BASF), Paliogen Red 3340 (BASF), Lithol Fast Scarlet L4300 (BASF), combinations of the above and similar.

WAX In addition to the polymeric resin, the organic pigments of the present disclosure may also contain a wax, which may be either a single type of wax or a mixture of two or more different waxes. A unique wax can be added to the organic pigment formulations, for example, to improve particular properties of organic pigment such as the particle form of organic pigment, the presence and amount of wax on the surface of the organic pigment particle, characteristics of loaded and / or melting, brightness, displacement, displacement properties and the like. Alternatively, a combination of waxes can be added to provide multiple properties to the organic pigment composition.

When included, the wax may be present in an amount, for example, from about 1% by weight to about 25% by weight of the organic pigment particles, in embodiments, from about 5% by weight to about 20% by weight of the organic pigment particles.

Waxes that can be selected include waxes having, for example, a weight average molecular weight from about 500 to about 20,000, in modalities, from approximately 1,000 to approximately 10,000. Waxes that can be used include, for example, polyolefins such as polyethylene waxes, polypropylene waxes and polybutene waxes such as those commercially available from Allied Chemical and Petrolite Corporation, for example, polyethylene waxes P0LYWAXMR from Baker Petrolite , wax emulsions available from Michaelman, Inc., and Daniels Products Co., EPOLENE N-15MR, commercially available from Eastman Chemical Products, Inc., and VISCOL 550-PMR, a low molecular weight, weight-average polypropylene available of Sanyo Kasei KK; waxes based on such plants, such as carnauba wax, rice wax, candelilla wax, sumacs wax and jojoba oil; waxes based on animals such as beeswax; mineral-based waxes and petroleum-based waxes such as montana wax, ozokerite, ceresin wax, paraffin wax; microcrystalline wax and Fischer-Tropsch waxes; aster waxes obtained from higher fatty acids and higher alcohols, such as stearyl stearate and behenyl behenate; aster waxes obtained from higher fatty acids and monovalent or multivalent lower alcohol, such as butyl stearate, propyl oleate, glyceride monostearate; glyceride distearate, pentaerythritol tetrabehenate; aster waxes obtained from higher fatty acids and alcohol multimers multivalent, such as diethylene glycol monostearate; dipropylene glycol distearate, diglyceryl distearate and triglyceryl tetrastearate; sorbitan higher fatty acid ester waxes such as sorbitan monostearate and higher fatty acid ester waxes and cholesterol such as cholesteryl stearate. Examples of functionalized waxes that can be used include, for example, amines, amides, for example AQUA SUPERSLIP 6550MR and SUPERSLIP 6530MR available from Micro Powder Inc .; fluorinated waxes, for example, POLYFLUO 190MR, POLYFLUO 200MR, POLYSILK 19MR and POLYSILK 14MR available from Micro Powder Inc .; mixed fluorinated amide waxes, for example MICROSPERSION 19MR available from Micro Powder Inc .; imides, esters, quaternary amines, carboxylic acids or acrylic polymer emulsion, for example JONCRYL 74MR, 89MR, 130MR, 537MR and 538MR, all available from SC Johnson Wax; and polypropylenes and chlorinated polyethylenes available from Allied Chemical and Petrolite Corporation and SC Johnson wax. Mixtures and combinations of the above waxes can also be used in modalities. Waxes can be included, for example, as fuser roll release agents.

PREPARATION OF ORGANIC PIGMENT The organic pigment particles can be prepared by any method within the scope of those skilled in the art. Although the modalities in relation to the Production of organic pigment particles are described in the following with respect to emulsion-aggregation processes, any suitable method can be used to prepare organic pigment particles, which includes chemical processes such as suspension and encapsulation processes described in the United States patent. U.S. Nos. 5,290,654 and 5,302,486, the description of each of which is incorporated herein by reference in its entirety. In embodiments, the organic pigment compositions and the organic pigment particles can be prepared by aggregation and coalescence processes in which the smaller sized resin particles are added to the appropriate organic pigment particle size and then coalesced to obtain the shape and particle morphology of final organic pigment.

In embodiments, the organic pigment compositions can be prepared by emulsion-aggregation processes such as a process that includes adding a mixture of an optional wax and any other desired or required additive and emulsions including the resins described above, optionally with surfactants, as described above and then coalescing the aggregate mixture. A mixture can be prepared by adding an optional wax or other materials, which optionally can also be in one or more dispersions including a surfactant, to the emulsion, which may be a mixture of two or more emulsions containing the resin. The pH of the resulting mixture can be adjusted by an acid (i.e., a pH adjuster) such as, for example, acetic acid, nitric acid or the like. In embodiments, the pH of the mixture can be adjusted from about 2 to about 4.5. Additionally, in embodiments, the mixture can be homogenized. If the mixture is homogenized, homogenization can be carried out by mixing from about 600 to about 4,000 revolutions per minute (rpm). Homogenization can be carried out by any suitable means including, for example, an IKA ULTRA TURRAX T50 probe homogenizer or a Gaulin 15MR homogenizer.

After the preparation of the above mixture, in general, an aggregation agent can be added to the mixture. Suitable aggregation agents include, for example, aqueous solutions of a divalent cation or a multivalent cation material. In the present embodiments, a polyaluminium halide specifically polyaluminium chloride (PAC) is used. PAC is a stronger multivalent flocculant compared to aluminum sulfate, which is a divalent flocculant. It has been discovered that PAC unexpectedly improves surface morphology by reducing the amount of styrene-acrylate on the surface. It is considered that multivalent PAC helps maintain the styrene-acrylate latex with a higher acid value with respect to the core of the organic pigment particles.

When using the PAC, the manufacturing process is modified to extend the coalescence time (compared to that used with conventional flocculants such as aluminum sulfate) from about 1 hour to about 3 hours, or from about 1.5 hours to about 2.5 hours. It has been discovered that this modification of longer coalescence time is necessary to uniform the surface of the organic pigment and obtain optimal surface morphology.

Other aggregation agents that can be used include the corresponding bromide, fluoride or iodide and combinations thereof. In embodiments, the aggregation agent is present in the organic pigment composition in an amount from about 0.1 to about 1.0 percent, or from about 0.2 to about 0.8 percent, or from about 0.25 to about 0.5 percent by weight of the weight total of the organic pigment particles. In embodiments, the aggregation agent can be added to the mixture at a temperature that is below the glass transition temperature (Tg) of the resin. As described in above, the reduced coalescence temperature used is from about 70 to about 90 ° C, or from about 70 to about 80 ° C, or from about 70 to about 77 ° C.

The aggregation agent can be added to the mixture to form an organic pigment in an amount, for example, from about 0.1 parts percent (pph) to about 1 pph of the organic pigment particles, in embodiments, from about 0.25 pph to approximately 0.75 pph of the organic pigment particles.

The brightness of an organic pigment can be altered by the amount of metal ion retained, such as Al3 + in the particle. The amount of metal ion retained can be further adjusted by the addition of ethylenediaminetetraacetic acid (EDTA). In embodiments, the amount of metal ion retained, eg, Al3 +, in the organic pigment particles of the present disclosure can be from about 0.1 pph to about 1 pph, in embodiments, from about 0.25 pph to about 0.8 pph.

The description also provides a melt blending process to produce low cost and safe crosslinked thermoplastic binder resins for organic pigment compositions which have, for example, example, a low setting temperature and / or a high displacement temperature and which may show minimized or substantially zero vinyl displacement. In the process, the unsaturated base polyester resins or polymers are melt blended, that is, in the molten state under high shear conditions that produce substantially uniformly dispersed organic pigment constituents and process which provides a resin combination and an organic pigment product with optimized gloss properties (see, for example, U.S. Patent No. 5,556,732, incorporated herein by reference in its entirety). By "highly crosslinked" it is meant that the polymer involved is substantially crosslinked, ie, it is equal to or above the gel point. As used herein, the term "gel point" means the point at which the polymer is no longer soluble in solution (see, for example, U.S. Patent No. 4,457,998, incorporated herein by reference in its whole).

To control the aggregation and coalescence of the particles, in modalities, the aggregation agent can be dosed in the mixture with respect to time. For example, the agent can be dosed into the mixture for a period from about 5 to about 240 minutes, in embodiments, from about 30 to about 200 minutes The addition of the agent can also be performed while the mixture is maintained under agitated conditions, in embodiments, from about 50 rpm to about 1000 rpm, in embodiments, from about 100 rpm to about 500 rpm, and at a temperature that is below the Tg of the resin.

The particles can be allowed to aggregate until a predetermined desired particle size is obtained. A predetermined desired size refers to the desired particle size, as determined before the formation, wherein the particle size monitored during the growth process, as is known in the field until the particle size is reached. Samples can be taken during the growth process and analyzed, for example, with a Coulter Counter equipment, for average particle size. Aggregation in this way can be carried out by keeping the temperature elevated or by slowly increasing the temperature, for example, from about 40 ° C to about 65 ° C and by keeping the mixture at that temperature for a time from about 0.5 h. to about 6 h, in modalities, from about 1 h to about 5 h, while stirring is maintained, to provide the aggregated particles. Once the predetermined desired particle size is obtained, the growth process it stops. In embodiments, the predetermined desired particle size is within the above-mentioned organic pigment particle size ranges. In embodiments, the particle size may be from about 5.0 to about 6.0 mm, from about 6.0 to about 6.5 mth, about 6.5 to about 7.0 mm, from about 7.0 to about 7.5 pm.

The growth and conformation of the particles after the addition of the aggregation agent can be carried out under any suitable condition. For example, growth and conformation can be carried out under conditions in which aggregation occurs separately from coalescence. For separate aggregation and coalescence steps, the aggregation process can be carried out under shear conditions at an elevated temperature, for example from about 40 ° C to about 00 ° C, in embodiments, from about 45 ° C to about 80 ° C, which may be below the Tg of the resin.

After aggregation to the desired particle size, with the optional formation of a shell as described above, the particles can then coalesce to the desired final shape, coalescence is performed, for example, by heating the mixture to a temperature from about 55 ° C to about 100 ° C, in modalities, from about 65 ° C to about 75 ° C, which may be below the melting point of a crystalline resin to avoid plasticization. Higher or lower temperatures can be used, it being understood that the temperature is a fusion of the resins used.

The coalescence can be performed for a period from about 0.1 to about 9 h, in modalities, from about 0.5 to about 4 h.

After coalescence, the mixture is cooled to room temperature, for example from about 20 ° C to about 25 ° C. Cooling can be fast or slow, as desired. A suitable cooling method can include introducing cold water to a jacket around the reactor. After cooling, the organic pigment particles can optionally be washed with water and then dried. The drying can be carried out by any suitable method, for example lyophilized.

Organic pigments may exhibit favorable loading characteristics when exposed to extreme RH conditions. The low humidity zone (zone C) can be at approximately 12 ° C / 15% RH while the high humidity zone (zone A) can be at approximately 28 ° C / 85% RH. The organic pigments of the description can have a charge to mass ratio (Q / M) of original organic pigment, from about -5 pC / g to about -80 pC / g, in embodiments, from about -10 pC / g to about -70 pC / g and a final organic pigment loaded after mixing of surface additive from -15 pC / g to about -60 pC / g, in modalities, from about -20 pC / g to about -55 pC / g.

COVERING RESIN In embodiments, a cover can be applied to the shaped aggregate organic pigment particles. Any resin described above as suitable for the core resin can be used as the cover resin. The cover resin can be applied to the aggregated particles by any method within the scope of those skilled in the art. In embodiments, the cover resin may be in an emulsion that includes any surfactant described herein. The aggregate particles described above can be combined with the emulsion so that the resin forms a shell on the shaped aggregates. In embodiments, an amorphous polyester can be used to form a shell on the aggregates to form organic pigment particles having a core-shell configuration.

The organic pigment particles can have a diameter size from about 4 to about 8 μm. In embodiments, from about 5 to about 7 mm, the optimum cover component can be from about 26 to about 30% by weight of the organic pigment particles.

Alternatively, a thicker cover may be desirable to provide desirable loading characteristics due to a larger surface area of the organic pigment particle. In this manner, the cover resin may be present in an amount from about 30% to about 40% by weight of the organic pigment particles, in embodiments, from about 32 to about 38% by weight of the organic pigment particles, in embodiments, from about 34% to about 36% by weight of the organic pigment particles.

In modalities, a photoinitiator can be included in the cover, in this way, the photoinitiator can be in the core, in the cover or in both places. The photoinitiator may be present in an amount from about 1% to about 5% by weight of the organic pigment particles, in embodiments, from about 2% to about 4% by weight of the organic pigment particles.

The emulsions can have a solids loading from about 5% solids by weight to about 20% solids by weight, in embodiments, from about 12% solids by weight to about 17% solids by weight.

Once the desired final size of the organic pigment particles has been reached, the pH of the mixture can be adjusted with a base (i.e., a pH adjuster) to a value from about 6 to about 10, and in , from about 6.2 to about 7. The pH adjustment can be used to stop, that is, to slow the growth of the organic pigment. The base used to stop the growth of organic pigment may include any suitable base such as, for example, alkali metal hydroxides such as for example, sodium hydroxide, potassium hydroxide, ammonium hydroxide, combinations thereof and the like. In modalities, EDTA can be added to help adjust the pH to the desired values indicated above. The base can be added in amounts from about 2 to about 25% by weight of the mixture, in embodiments, from about 4 to about 10% by weight of the mixture. In embodiments, the cover has a greater Tg than the added organic pigment particles.

CARRIERS Various solid core or particle materials suitable for the carriers and developers of the present disclosure may be used. The characteristic particle properties include those which, in modalities, will allow the organic pigment particles to acquire a positive charge or a negative charge and the carrier cores that provide the desirable flow properties in the developer tank present in a generator apparatus. electrophotographic image. Other desirable properties of the core include, for example, suitable magnetic characteristics that allow magnetic brush formation in magnetic brush developing processes; desirable mechanical aging characteristics; and desirable surface morphology to allow high electrical conductivity of any developer including the carrier and a suitable organic pigment.

Examples of carrier particles or cores that can be used include iron and / or steel such as atomized iron or steel powders available from Hoeganaes Corporation or Pomaton S.p.A. (Italy); ferrites such as Cu / Zn-ferrite containing, for example, about 11% copper oxide, about 19% zinc oxide and about 70% iron oxide, including those commercially available from D.M. Steward Corporation or Powdertech Corporation, Ni / Zn-ferrite available from Powdertech Corporation, Sr (strontium) -ferrite containing, for example, about 14% strontium oxide and about 86% iron oxide, commercially available from Powdertech Corporation and Ba-ferrite; magnetites including those commercially available, for example, from Hoeganaes Corporation (Sweden); nickel; combinations thereof and similar. In embodiments, the polymer particles obtained can be used to coat carrier cores of any known type by various known methods and carriers which are then incorporated with a known organic pigment to form a developer for electrophotographic printing. Other suitable carrier cores are illustrated, for example, in U.S. Patent Nos. 4,937,166, 4,935,326 and 7,014,971, the description of each of which is incorporated herein by reference in its entirety and may include granular zirconium, granular silicon, glass, silicon dioxide, combinations thereof, and the like. In embodiments, suitable carrier cores can have an average particle size, for example, from about 20 mm to about 400 pm in diameter, in embodiments, from about 40 pm to about 200 pm in diameter.

In modalities, a ferrite can be used as the core, which includes a metal such as iron and at least one additional metal such as copper, zinc, nickel, manganese, magnesium, calcium, lithium, strontium, zirconium, titanium, tantalum, bismuth, sodium, potassium, rubidium, cesium , strontium, barium, yttrium, lanthanum, hafnium, vanadium, niobium, aluminum, gallium, silicon, germanium, antimony, combinations thereof and the like.

In some embodiments, the carrier coating may include a conductive component. Suitable conductive components include, for example, carbon black.

Many additives can be added to the carrier, for example, charge improver additives, including particulate amine resin such as melamine and certain fluoropolymer powders such as alkyl and methacrylate amino acrylates, polyamides and fluorinated polymers such as polyvinylidene fluoride and poly ( tetrafluoroethylene) and fluoroalkyl methacrylate such as 2,2-trifluoroethylmethacrylate. Other filler-enhancing additives which may be used include quaternary ammonium salts, including distearyl dimethyl ammonium methylsulfate (DDAMS), bis [1- (3,5-disutituido-2-hydroxyphenyl) azo] -3- (mono- substituted) -2-naphthalenenolate (2)] chromate (1), ammonium, sodium and hydrogen (TRH), cetylpyridinium chloride (CPC), FANK PINKMR D4830, combinations thereof and the like and other known effective bulking agents or additives . The additive filler components can be selected in various effective amounts such as from about 0.5 wt% to about 20 wt%, from about 1 wt% to about 3 wt%, based, for example, on the sum of the polymer / copolymer weights, conductive component and other load additive components. The addition of conductive components can act to further increase the negative triboelectric charge imparted to the carrier and thereby further increase the negative triboelectric charge imparted to the organic pigment, for example, in an electrophotographic development subsystem. The components can be included by roller mixing, drum treatment, milling, stirring, electrostatic powder cloud spraying, fluidized bed, electrostatic disk processing and electrostatic curtain, as described, for example, in U.S. Pat. No. 6,042,981, the disclosure of which is incorporated herein by reference in its entirety, and wherein the carrier coating is fused to the carrier core in either a rotary kiln or by passing it through a heated extruder apparatus.

Conductivity may be important for the development of semiconductor magnetic brush to allow good development of solid areas which may otherwise be weakly revealed. The addition of a polymeric coating of the present disclosure, optionally with a conductive component such as carbon black, can result in carriers with reduced developer tribo response with charge in relative humidity from about 20% to about 90%, in embodiments, from about 40% to approximately 80% so that the load is more consistent when the relative humidity changes. Therefore, there is less decrease in load at a high relative humidity which reduces the background organic pigment in the prints and less increase in the load and subsequently less loss of development with a low relative humidity, which results in a performance of Improved image quality due to improved optical density.

As indicated in the foregoing, in embodiments, the polymeric coating can be dried, after which time it can be applied to the core carrier as a dry powder. The powder coating process differs from conventional solution coating processes. The coating and solution requires a coating polymer whose composition and molecular weight properties allow the resin to be soluble in a solvent in the coating process. This requires components with relatively low Mw compared to the powder coating. The powder coating process does not require Solubility in solvent but requires that the resin coated as a particulate material with a particle size from about 10 nm to about 2 pm, in embodiments, from about 30 nm to about 1 mm, in embodiments, from about 50 nm to about 500 nm .

Examples of processes which can be used to apply the powder coating incl for example, combining the carrier core material and the resin coating by cascade roller mixing, drum treatment, milling, stirring, cloud spraying. electrostatic powder, fluidized bed, electrostatic disk processing, electrostatic shades, combinations thereof and the like. When the carrier particles coated with resin are prepared by a powder coating process, most of the coating materials can be fused to the carrier surface to thereby reduce the number of organic pigment impact sites on the carrier. The melting of the polymeric coating can be caused by mechanical impact, electrostatic attraction, combinations thereof and the like.

After application of the resin to the core, heating can be initiated to allow the flow of the coating material on the surface of the core carrier. The concentration of the coating material, in embodiments, powder particles and the heating parameters can be selected to allow the formation of a continuous film of the coating polymers on the surface of the carrier core to allow only the selected areas of the carrier core be coated. In embodiments, the carrier with the polymer powder coating can be heated to a temperature from about 170 ° C to about 280 ° C, in modalities, from about 190 ° C to about 240 ° C, for a period of time, for example , from about 10 min. to about 180 min., in embodiments, from about 15 min. to about 60 min., to allow the polymer coating to melt and fuse to the carrier core particles. After incorporation of the powder on the surface of the carrier, heating can be initiated to allow the flow of the coating material on the surface of the carrier core. In embodiments, the powder can be fused to the carrier core either in a rotary kiln or by passing it through a heated extr apparatus, see, for example, U.S. Patent No. 6,355,391, the description of which is incorporated in FIG. the present as a reference in its entirety.

In modalities, the coating coverage ranges from about 10% to about 100% of the carrier core. When the selected areas of the metal carrier core remain uncoated or exposed, the carrier particles may possess electrically conductive properties when the core material is a metal.

The coated carrier particles can then be cooled, in modalities up to room temperature, and can be recovered for use in the developer formation.

In embodiments, the carriers of the present disclosure may include a core, in embodiments, a ferrite core, having a size from about 20 mm to about 100 mm, in modalities, from about 30 pm to about 75 p, coated with from about 0.5% to about 10% by weight, in embodiments, from about 0.7% to about 5% by weight, of the polymer coating of the present disclosure, which optionally includes carbon black.

Thus, with the carrier compositions and processes of the present disclosure, developers can be formulated with selected high triboelectric charge characteristics and / or conductivity values using many different combinations.

REVELATORS The organic pigment particles formed from this way they can be formulated in a developing composition. The organic pigment particles can be mixed with carrier particles to obtain a two component developer composition. The concentration of organic pigment in the developer can be from about 1% to about 25% by weight of the total weight of the developer, in embodiments, from about 2% to about 15% by weight of the total weight of the developer.

GENERATION OF INGEN Organic pigments can be used for electrophotographic processes including those described in U.S. Patent No. 4,295,990, the disclosure of which is incorporated herein by reference in its entirety. In embodiments, any type of image developing system can be used in an image developing device that includes, for example, magnetic brush development, hybrid-free development (HSD) and the like. Those and similar development systems are within the scope of experts in the field.

It is considered that the organic pigments of the present disclosure can be used in any suitable process for forming an image with an organic pigment, which include in different applications in xerographic applications.

Using the organic pigments of the present disclosure images can be formed on substrates including flexible substrates having an organic pigment stack height of from about 1 mm to about 6 mm, in modalities, from about 2 mm to about 4.5 mih, in modalities , from about 2.5 to about 4.2 pm.

In embodiments, the organic pigment of the present disclosure can be used for a xerographic printing protective composition that provides overprint coating properties including, but not limited to, thermal and light stability and sag resistance, particularly in printing applications. commercial. More specifically, such overprint coating, as has been considered, has the ability to allow overwriting, reduce or avoid thermal fractures, improve melting, reduce or avoid document displacement, improve print performance and protect a image of the sun and the like. In embodiments, the overprint compositions can be used to improve the overall appearance of the xerographic prints due to the ability of the compositions to fill the roughness of the xerographic substrates and the organic pigments, whereby a level film is formed and improves brightness The following examples are sent to illustrate embodiments of the description. The examples are intended to be illustrative only and are not intended to limit the scope of the description. In addition, parts and percentages are by weight unless indicated otherwise. As used herein, "room temperature" refers to the temperature from about 20 ° C to about 30 ° C.

EXAMPLES The examples set forth herein below are shown to illustrate embodiments of the present disclosure. These examples are intended to be illustrative only and are not intended to limit the scope of the present disclosure. In addition, the parts and percentages are by weight, unless indicated otherwise. Examples and comparative data are also provided.

CONTROL EXAMPLE 1 of Control organic pigment: preparation of a 22% styrene-acrylate core (latex with particle size of 162 nm) particle of black organic pigment a 70 ° C In a 2 1 reactor, 43 g of amorphous polyester emulsion (FXC42, available from Kao Corporation), 47 g of amorphous polyester emulsion (FXC56, available from Kao Corporation), 81 g of styrene-acrylate latex are combined. (consisting of 23.5% n-butyl acrylate, 76.5% styrene with an average molecular weight of 55,000 g / mol, particle size 162 nm), 29 g of crystalline polyester emulsion, 43 g of wax, 9.6 g of pigment cyan, 57 g of black pigment (Nipex-35), 0.7 g of surfactant (Dowfax) and 534 g of deionized water (DI). Then 2.7 g of aluminum sulfate (Al2 (SO4) 3) are mixed with 33 g of DI water are added to the suspension under homogenization at 3000-4000 rpm. The reactor is set at 260 rpm and heated to 42 ° C to add the organic pigment particles. When the size reaches 4.8-5 mm, a cover coating is added which consists of 69 g of amorphous polyester emulsion (FXC42), 74 g of amorphous polyester emulsion (FXC56) with 1.15 g of surfactant (Dowfax) and all the pH is adjusted to 3.3 using 0.3 M nitric acid. The reaction is further heated to 50 ° C. When the particle size of the organic pigment reaches 5.6-6 micrometers, the stop with the pH of the suspension starts, which is adjusted to 4.5 using a 4% NaOH solution. The rpm of the reactor decreases to 220 followed by the addition of 5.77 grams of a chelating agent (VersenelOO) and more NaOH solution until the pH reaches 7.8. The reactor temperature changes gradually to 70 ° C. The pH of the solution is maintained at 7.8 or more up to 70 ° C. Once at the coalescence temperature, the pH of the suspension is reduced to 6.0 using shock absorber 5.7 and allowed to co-oscillate for about 1 hour until the particle circularity is between 0.955 -0.960, as measured by the Flow Partiolle Image Analysis (FPIA). The suspension is then cooled by quenching in 770 g of ice with DI. The final particle size is 5.90 microns, GSDv 1.21, GSDn 1.22 and a circularity of 0.958. The organic pigment is then washed and lyophilized.

EXAMPLE 1 EXAMPLE 1 OF ORGANIC PIGMENT: PREPARATION OF PARTICLE OF ORGANIC BLACK HYBRID PIGMENT WITH Al2 (SC> 4) 3 In a 2 1 reactor, 43 g of amorphous polyester emulsion (), 47 g of amorphous polyester emulsion (FXC56), 82 g of styrene-latex are combined. acrylate, (consisting of 23.5% N-butyl acrylate, 76. 5% styrene with an average molecular weight of 55,000 g / mol, particle size of 162 nm, particle size 141 nm), 29 g of crystalline polyester emulsion, 49 g of wax, 9.6 g of cyan pigment, 57 g of black pigment (Nipex-35), 0.7 g of surfactant (Dowfax) and 534 g of water GAVE. Then 2.7 g of aluminum sulphate (Al2 (SO4) 3 mixed with 33 g of DI water is added to the suspension under homogenization at 3000-4000 rpm, the reactor is adjusted to 260 rpm and heated to 42 ° C to add the organic pigment particles. When the size reaches 4.8-5 mp, a cover coating is added which consists of 69 g of amorphous polyester emulsion (FXC42), 74 g of amorphous polyester emulsion (FXC56) with 1.15 g of surfactant (Dowfax) and everything is adjusted to pH of 3.3 with 0.3M nitric acid. The reaction is further heated to 50 ° C. When the organic pigment particle size reaches 5.6-6 microns, the stop is started with the pH of the suspension which is adjusted to 4.5 using a 4% NaOH solution. The rpm of the reactor is decreased to 220 followed by the addition of 5.77 grams of a chelating agent (VersenelOO) and more NaOH solution until the pH reaches 7.8. The reactor temperature changes gradually to 70 ° C. The pH of the suspension is maintained at 7.8 or higher up to 70 ° C. Once at the coalescence temperature, the pH of the suspension is reduced to 6.0 using buffer pH 5.7 and is subjected to coalescence for about 1 hour until the circularity of the particles is between 0.955-0.960, as measured by the Flow Partiol Image instrument Analysis (FPIA). The suspension is then cooled by quenching in 770 g of ice with DI. The final particle size is 6.0 micrometers, GSDv 1.21, GSDn 1.24 and a circularity of 0.955. The organic pigment after washing and freeze-drying.

EXAMPLE 2 EXAMPLE 2 OF ORGANIC PIGMENT: PREPARATION OF A PARTICLE OF PIGMENT ORGANIC BLACK HYBRID WITH PAC In a 2 1 reactor, 43 g of amorphous polyester emulsion (FXC42), 47 g of amorphous polyester emulsion (FXC56), 82 g of styrene-acrylate latex, (consisting of 23.5% N-acrylate) are combined. butyl, 76.5% styrene with an average molecular weight of 55,000 g / mol, particle size of 141 nm, particle size 141 nm), 29 g of crystalline polyester emulsion, 43 g of wax, 9.6 g of cyan pigment, 57 g of black pigment (Nipex-35), 0.7 g of surfactant (Dowflax) and 534 g of DI water. Then 2.7 g of polyaluminium chloride (PAC) are mixed with 24 g of 0.02M nitric acid which is added to the suspension under homogenization at 3000-4000 rpm. The reactor is adjusted to 260 rpm and heated to 42 ° C to add the organic pigment particles. When the size reaches 4.8-5 mm, a cover coating is added which consists of 69 g of amorphous polyester emulsion (FXC42), 74 g of amorphous polyester emulsion (FXC56) with 1.15 g of surfactant (Dowfax) and everything is adjusted to pH 3.3 using 0.3M nitric acid. The reaction is further heated to 50 ° C. When the particle size of organic pigment reaches 5.6-6 micrometers, the stop is initiated with the pH of the suspension that is adjusted to 4.5 using a 4% NaOH solution. The rpm of the reactor is decreased to 220 followed by the addition of 5.77 grams of a chelating agent (VersenelOO) and more NaOH solution until the pH reaches 7.8. The reactor temperature changes gradually to 70 ° C. The pH of the suspension is maintained at 7.8 or higher up to 70 ° C. Once at the coalescence temperature, the pH of the suspension is reduced to 6.0 using buffer pH 5.7 and is coalesced for approximately 2 hours until the circularity of the particles is between 0.955-0.960, as measured by the Flow Particle Image instrument Analysis (FPIA). The suspension is then cooled by quenching in 770 g of ice with DI. The final particle size is 6.3 micrometers, GSDv 1.23, GSDn 1.25 and a circularity of 0.955. The organic pigment after washing and freeze-drying.

COMPARATIVE EXAMPLES ORGANIC PIGMENT XEROX 700 (CYAN OR BLACK) This commercially available organic pigment is used as a comparison with the organic pigments of the invention. The organic pigment Xerox 700 is constituted by an organic pigment of aggregation by emulsion, where the core is constituted of approximately 6 to 7 weight percent of resin crystalline, 5 to 6 weight percent of cyan or black pigment, 8 to 10 weight percent of wax and about 50 to about 52 weight percent of amorphous polyester resin and wherein the shell is from about 28 percent in weight of organic pigment.

Organic Pigment Xerox Docucolor 2240 Cyan This commercially available organic pigment is used as a comparison with respect to the organic pigments of the invention. The Xerox Docucolor 2240 organic pigment is made up of an organic emulsion aggregation pigment, wherein the core is made up of 5 to 6 weight percent of cyan or black pigment, 10 to 12 weight percent of wax and approximately 54 to about 56 weight percent styrene-acrylate resin, and wherein the shell is a styrene-acrylate resin from about 28 weight percent organic pigment.

Table 1 shows the traits and properties of the control and examples 1 and 2 of organic pigment as well as an organic pigment based on polyester added by emulsion (organic pigment Xerox 700). The control and examples 1 and 2 of organic pigment all incorporate at least 20% styrene-acrylate latex. Example 2 of organic pigment has PAC as the flocculant.

TABLE 1 The SEM images were taken from the control and Examples 1 and 2 of organic pigment, as shown in Figure 1. As can be seen from Figure 1, the surface is improved with a polystyrene / acrylate latex of smaller size (the control compared to example 1 of organic pigment) and an even larger improvement is observed when the flocculant is changed to PAC (example 2 of organic pigment).

These organic pigments were then analyzed for loading and melting performance, the results are found later.

DEVELOPMENT PERFORMANCE RESULTS The loading performance is comparable to that of the standard EA polyester organic pigment, however, the main concern is the initiation of blocking and the% heat cohesion. These two properties are not as good as those of the organic polyester control pigment, however, after some investigation it was observed that the surface morphology of the organic pigments is worse than that of the polyester control organic pigment. As seen in the SEM images of organic pigment, the organic pigment surface contains a lot of polystyrene / acrylate latex and some wax particles.

The wax content is typical; however, polystyrene / acrylate on the surface prevents the organic pigment additives from adequately covering the surface of the organic pigment and also has a negative impact on the performance of the organic pigment.

Surprisingly, when the flocculant is changed to PAC to flocculate the organic pigment, You can see that it improves the surface of the organic pigment. The polystyrene / acrylate latex does not protrude to the surface of the organic pigment, but rather remains more in the center of the organic pigment.

TABLE 2 As can be seen from table 2 above, the dielectric loss of organic pigment remains comparable to that of the polyester control organic pigment but even improves with the improved surface morphology.

Table 3 below shows the blocking results of organic pigment for the various hybrid examples.

TABLE 3 The blocking for example 2 of organic pigment is within the experimental error of polyester control organic pigment (Xerox 700 organic pigment); while the two previous samples (the control and example 1 of organic pigment) have insufficient perceptible.

Figure 2 shows the manner in which the% heat cohesion of the organic pigment of the present embodiment also improves compared to the control and example 1 of organic pigment, without PAC as the flocculant.

SUMMARY OF FUSION RESULTS The brightness, corrugation and hot particle displacement data were collected with fused samples on Color Xpressions Select (90 gsm) using an internal fusion fixture. The organic pigments are within the experimental uncertainty of the reference pigment organic control polyester samples.

CONTROL The print brightness curve of this hybrid organic pigment is between the Xerox 700 organic pigment, Xerox Docucolor 2240 comparative reference samples and has a lower peak brightness (57 gu versus 63 gu). The temperature needed to reach 50 units of gloss at 158 ° C while the Xerox Docucolor 2240 organic pigment requires 166 ° C and the organic polyester control pigment requires 146 ° C.

The fixed corrugated minimum fixing temperature (MFT) of this hybrid organic pigment is lower than that of the organic pigment Xerox 700 (117 ° C versus 123 ° C) and much lower than that of the organic pigment Xerox Docucolor 2240 (117 ° C versus 143 ° C). Laboratory-scale and cabinet-scale particles may have lower MFT of corrugation fixation than particles at production scale.

There is no hot displacement of organic pigment to the fuser roller at 210 ° C, resulting in a wide melting latitude.

EXAMPLES 1 AND 2 OF ORGANIC PIGMENT The print brightness of this hybrid organic pigment approximates the design brightness and the cabinet-scale polyester pigment and the MFT of corrugated fixing is less than the MFT of organic polyester production pigment. Both hybrid organic pigments have a very low corrugation fixation MFT and the gloss curve approximates the glossiness curve of organic polyester pigment. The lower coalescence curve and the particles Styrene acrylate latex small have no significant impact on the fusion performance of the hybrid design.

The fusion results are consistent with previous hybrid particles.

It will be appreciated that several of the features and functions described in the foregoing and others, or alternatives thereof, may be desirably combined in many other systems or different applications. In addition, various alternatives, modifications, variations or improvements not foreseen or not anticipated herein may be subsequently made by those experts in the field, which are also intended to be encompassed by the following claims.

Unless specifically mentioned in a claim, the steps or components of the claims should not be implied or considered from the description or any other claim with respect to any particular order, number, position, size, shape, angle, color or material. .

All references mentioned herein are incorporated herein by reference in their entirety.

It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims

CLAIMS Having described the invention as above, the content of the following claims is claimed as property:

1. An organic pigment composition, characterized in that it comprises: organic pigment particles having a core, wherein the core comprises: a resin, a dye, a wax, and polyaluminium chloride, wherein the resin comprises a styrene-acrylate resin, a crystalline polyester resin and an amorphous polyester resin; Y a cover placed on the core.

2. The organic pigment composition according to claim 1, characterized in that the aggregation agent is present in the organic pigment composition in an amount from about 0.1 to about 1.0 weight percent of the total weight of the organic pigment particles.

3. The organic pigment composition according to claim 1, characterized in that the styrene acrylate resin is present in the core in a amount from about 5 to about 30 weight percent of the total weight of the core.

4. The organic pigment composition according to claim 1, characterized in that the crystalline polyester resin in the core is present in an amount from about 5 to about 8 weight percent of the total weight of the organic pigment and wherein the polyester resin Amorphous in the core is present in an amount of from about 20 to about 30 weight percent of the total weight of the organic pigment composition.

5. The organic pigment composition according to claim 1, characterized in that the amorphous resin in the shell is present in an amount from about 30 to about 36 weight percent of the organic pigment composition.

6. The organic pigment composition according to claim 1, characterized in that the amorphous polyester resin is selected from the group consisting of poly (bisphenol A alkoxylated co-fumarate co-terephthalate co-succinate of dodecenyl), poly (bisphenol propoxylated co- fumarate), poly (bisphenol ethoxylated co-fumarate) and mixtures thereof.

7. The organic pigment composition according to claim 1, characterized in that the cover comprises an amorphous polyester resin.

8. The organic pigment composition according to claim 1, characterized in that the coating comprises from about 30 to about 36 weight percent of the organic pigment composition.

9. The organic pigment composition according to claim 1, characterized in that it has a minimum melting temperature from about 100 to about 130 ° C.

10. The organic pigment composition according to claim 1, characterized in that it has a dielectric loss from about 20 to about 40.

11. The organic pigment composition according to claim 1, characterized in that it is an organic emulsion aggregation pigment.

12. A developer, characterized in that it comprises: an organic pigment composition; Y an organic pigment carrier, wherein the organic pigment composition comprises: organic pigment particles having a core, wherein the core comprises: a resin, a dye, a wax, and polyaluminium chloride, wherein the resin comprises a styrene-acrylate resin, a crystalline polyester resin and an amorphous polyester resin; Y a cover placed on the core.

13. The developer according to claim 12, characterized in that the aggregation agent is present in the organic pigment composition in an amount from about 0.1 to about 1.0 weight percent of the total weight of the organic pigment particles.

14. A method for making an organic pigment, characterized in that it comprises: joining by mixing and emulsifying a resin, a dye and a wax, wherein the resin comprises a styrene-acrylate resin, a crystalline polyester resin to form a latex emulsion; add polyaluminium chloride to the latex emulsion; adding the latex emulsion to form organic pigment particle cores, wherein the organic pigment particle cores comprise the styrene-acrylate resin, the crystalline polyester resin and the amorphous polyester; form a cover over the particle cores of organic pigment to form organic pigment particles; coalescing the organic pigment particles; Y cool the organic pigment particles.

15. The method according to claim 9, characterized in that the polyaluminium chloride is added to the latex emulsion at a temperature which is below the glass transition temperature (Tg) of the styrene-acrylate resin and the polyester resin crystalline

16. The method according to claim 14, characterized in that the organic pigment particles are coalesced at a reduced temperature from about 70 to about 90 ° C.

17. The method according to claim 14, characterized in that the aluminum chloride is added to the latex emulsion in an amount from about 0.1 parts per 100 to about 1 parts per 100 of the organic pigment particles.

18. The method according to claim 14, characterized in that the latex emulsion has a particle size from about 100 to about 159.

19. The method of compliance with claim 18, characterized in that the latex emulsion has a particle size from about 100 to about 140.

20. The method according to claim 14, characterized in that the coalescence stage requires from about 1 hour to hours.