WO1987000308A1 - Dispersion de resine - Google Patents

Dispersion de resine Download PDF

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Publication number
WO1987000308A1
WO1987000308A1 PCT/JP1986/000333 JP8600333W WO8700308A1 WO 1987000308 A1 WO1987000308 A1 WO 1987000308A1 JP 8600333 W JP8600333 W JP 8600333W WO 8700308 A1 WO8700308 A1 WO 8700308A1
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WO
WIPO (PCT)
Prior art keywords
weight
formula
monomer
alkyl
copolymer
Prior art date
Application number
PCT/JP1986/000333
Other languages
English (en)
Japanese (ja)
Inventor
Toyokichi Tange
Masatoshi Maruyama
Shoko Nishizono
Tomohiko Minagawa
Original Assignee
Toa Paint Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Toa Paint Co., Ltd. filed Critical Toa Paint Co., Ltd.
Publication of WO1987000308A1 publication Critical patent/WO1987000308A1/fr

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
    • G03G9/131—Developers with toner particles in liquid developer mixtures characterised by polymer components obtained by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the present invention provides a novel resin dispersion useful for an electrophotographic liquid developer for offset masters, and is particularly excellent in dispersion stability, free from bleeding and background stain, and capable of removing an image which is eroded by rope.
  • the present invention relates to a novel liquid dispersion which gives a liquid developer to be formed.
  • a resin dispersion for an electrophotographic liquid developer includes a polymer that is soluble in a low dielectric constant, highly electrically insulating organic solvent (hereinafter referred to as a “solvent”) and a polymer that is insoluble in the solvent.
  • a resin dispersion eg, JP-A-53-54023
  • JP-A-53-54023 a resin dispersion obtained by subjecting the resulting monomer to graft polymerization, but such a resin composition is difficult to construct.
  • the developer often generates gel and it is difficult to obtain a stable developer.
  • the polar functional groups are simply The stability is improved to some extent with the resin dispersion liquid added to the hydrophilic polymer, but image blurring (outlined outline) and background stains occur frequently, especially in electrophotographic liquid development for offset masters.
  • image blurring outlined outline
  • background stains occur frequently, especially in electrophotographic liquid development for offset masters.
  • the present invention solves the above-mentioned problems of the prior art, and has excellent stability, is free from image bleeding and background smear, and has an excellent W printability, and a resin dispersion for an electrophotographic liquid developer.
  • the background stain refers to a development in which a print ink adheres to a non-image portion in offset printing to cause stain.
  • R 4 each independently represents hydrogen, C, the number of carbon atoms of ⁇ s alkyl or each alkyl le part of the alkoxyalkyl. 1 to 4, R 3 and R 3 represents C, and 1-4 alkylene independently , X represents hydrogen or methyl.] 0.5 to 12% by weight, preferably 2 to 12% by weight, most preferably 2 to 6% by weight and c) up to 20 % by weight of acrylic acid or methacrylic acid.
  • alkyl esters and Z or C 3 ⁇ 8 cycloalkyl esters 0 Ma 9.5 wt%, preferably 2-48 wt%, most preferably 5 to 28% by weight of (but above I), mouth) and c) At least a part of the monomer of the formula (I) has its amino group quaternized by a 4-ammonifying agent.
  • Y represents one COOR 5 , one OCOR s or one OR s
  • R s represents 0 ⁇ -20 alkyl.
  • R s is cycloalkyl or a C 3 ⁇ 8 represent Ararukiru carbon atoms from 1 to 3 alkyl moieties
  • the organic mercaptan having at least one thiol group has a sulfur content of 0 to 2% by weight, preferably 0.03 to 2% by weight, most preferably 0.1 to 1% by weight, particularly 0.2 to 0.3% by weight,
  • an electrophotographic liquid for an offset master comprising: an electrophotographic liquid for an offset master; A callus dispersion passed through the imaging agent is provided.
  • Examples of the monomer of the formula (I) of the formula (I) contained in the insoluble copolymer include methacrylic acid or esters of acrylic acid and the following alcohols; Monoethyl alcohol, mono- or dimethylaminoethyl, mono- or dimethylamido / propyl alcohol, mono- or diethylaminobubyl alcohol, mono- or diphenylaminomethyl alcohol, mono- or diphenylamino-methyl alcohol, di-methoxy alcohol Monoethyl alcohol, diethoxyaminoethyl alcohol, mono- or dimethylaminopropylaminoethyl alcohol, mono- or getylamino knob-mouth bilaminoethyl alcohol.
  • dialkylaminoalkyl esters of methacrylic acid are preferred, and dimethylaminoethyl esters and methylaminoethyl esters of methacrylic acid are particularly preferred.
  • Examples of the monomer of the formula (I) of the formula (I) include amides of methacrylic acid or acrylic acid with the following amines: mono- or dimethylamine, mono- Or getylamine, mono- or dibupyramine, mono- or dimethylaminoethylamine, mono- or dimethylaminoethylamine, mono- or dimethylamino-pyruamine and mo //-ethylamine viramine.
  • acid amides of methacrylic acid or acrylic acid and dialkylamine or dialkylaminoalkylamine especially dimethylamine, getylamine or dimethylamine. Nobuguchi Vilamin acid amide is preferred.
  • the monomer of the formula (I) contained in the insoluble copolymer may contain one kind or two or more kinds. If the content of these monomers exceeds 12% by weight, the image When the hydrophilicity of the ink is increased, the ink receptivity at the time of 7-set printing is enhanced, which is not preferable. When the amount is less than 0.5% by weight, the printing durability is unfavorably deteriorated.
  • At least one part of the monomer of the formula (I) contained in the insoluble copolymer (particularly, a monomer contained at or near the surface of the dispersed particles has an amino group of a quaternary ammonium monomer). It is a quaternary ammonium which has been converted to a quaternary ammonium by the use of an insoluble agent whose amount is 0.1 to 5 mol% per monomer of the formula (I).
  • a copolymer is preferable, and an insoluble copolymer having a content of 0.5 to 2 mol% is more preferable. If the amount of the quaternary ammoniating agent exceeds 5 mol%, the image density is lowered. Since the hydrophilicity becomes strong, the affinity with the offset ink after plate-making is lowered, which is not preferable. On the other hand, if it is less than 0.1 mol%, the printing performance is lowered, which is not preferable.
  • Examples of the quaternary ammoxidizing agent used include organic compounds exhibiting acidity, such as aliphatic or aromatic carboxylic acids, aliphatic or aromatic halides, and aliphatic. Or aromatic sulfonic acid and the like, for example, dimethyl sulfuric acid, methyl chloride and chlorinated chloride and the like can be mentioned. Dimethyl sulfate, methyl chloride and the like are preferably used.
  • esters of lylic acid with the following alcohols n-butanol, isobutanol / n-hexyl alcohol, 2-ethylhexyl alcohol, n-octa / nitl, n-nonyl alcohol, iso- / Nyl alcohol, n-decyl alcohol, iso-decyl alcohol, n-dodecyl alcohol, n-tridecyl alcohol, n-octadecyl alcohol, ⁇ ⁇ -brobanol, iso-propanol, ethanol, methanol.
  • ( ⁇ to 12 alkyl esters of methacrylic acid are preferred, and n-butyloctyl ester or 2-ethylhexyl ester is
  • the C 3 ⁇ a cycloalkyl ester of Akuriru acid or Metakuriru acids c) contained in the copolymer insoluble can be exemplified an ester of a following alcohol and Metaaku acrylic acid or ⁇ click acrylic acid; Shikurobu port Birua alcohol, Cyclohexyl alcohol, cyclohexyl alcohol, cyclopentyl alcohol and cyclooctyl alcohol. Among them, the hexyl ester of meta-atallylic acid is preferred.
  • alkyl esters and z or c 3 ⁇ 8 consequent opening alkyl Es ether may be contained one or two or more, preferably but contained 2-4 8 wt%, the multi exceed 4 8 wt% If it is too small, it is not preferable because the image density is lowered and printability is enhanced. If it is less than 2% by weight, the particle diameter becomes large and sedimentation stability is unfavorably increased.
  • Insoluble copolymers include vinyl acetate, monomers of formula (I) and acrylic acid. Or C Metaata acrylic acid, other than the ⁇ 20 alkyl esters and / or C 3 - 8 cycloalkyl esters, the ingredients, optionally in a range that does not adversely affect the various properties such as stability and scumming and Si printing properties Can be contained.
  • Monomers of the formula ()) of-) contained in the soluble copolymer include n-butyl ester, isopropyl ester, n-hexyl ester of methacrylic acid or acrylic acid, and ⁇ - old Kuchiruesuteru, Kishiruesute to 2 Echiru Le, n- dodecyl ester, n- Application Benefits decyl ester, .pi.
  • the methacrylate 51 such as decyl ester is made of acrylate, fatty acid vinyl such as vinyl brobionate, vinyl acetate, and vinyl versatate, and vinyl ether such as vinyl n-butynole ether and vinyl isobutyl ether. Examples can be given.
  • Preferred monomers of formula ( ⁇ ) are of the formula CH 3
  • 2-ethylhexyl methacrylate and n-octyl acrylate are particularly preferred.
  • the amount of the monomer of the formula (II) is more than 95%, it is not preferable because the bleeding of the image and the printability are deteriorated, and if the amount is too small, the sedimentation stability is lowered. Not preferred.
  • Suitable monomers of the formula (IB) is also C 3 ⁇ 8 consequent opening alkyl meth Ata Li rate is C 3 ⁇ 8 cycloalkyl Atari rate, preferably Kishirumeta Atari rate or consequent opening Arukiruakuri rate especially cyclohexylene It is.
  • the amount of the monomer of the formula (m) exceeds 85% by weight and is too large, the solubility is lowered and the stability of the dispersion is lowered, which is not preferable. If the amount is less than 5% by weight, image bleeding occurs. It is not preferable because the property is lowered.
  • Organic mercatanes having at least one thiol group (contained in soluble copolymers) have from 1 to about 4 thiol groups per molecule and from 1 to about 12 carbon atoms per thiol group. And preferably contains 2 to 8 carbon atoms.
  • These organic mercaptans can contain other substituents in addition to the hydrocarbon groups, such as carboxylic acid groups, hydroxy groups, ether groups, ester groups, sulfido groups, amine groups.
  • the base group is included.
  • Examples of useful mercaptans include methyl mercaptan, ethyl mercaptan, butyl mercaptan, octyl mercaptan, vinyl mercaptan, mercaptoethanol, mercaptoprohanol, mercaptobutanol, mercaptoacetic acid, mercaptoacetic acid.
  • Probionic acid titanium linoleic acid, benzylmercaptan, phenylmenolecabbutane, cyclohexane Xylmer ⁇ butane, 1-thioglycerol, 2,2'-dimer * Butjethyl ether, 2,2 Dimercapto dibuvir ether, 2,2'-Dimerbuto diisobrovir ether, 3,3'-Dimercapto jibulovir Ter, 2,2'-dimercaptocetyl sulfide 7, 3,3 dimercapto jib mouth bilsulfide, 1,11-dimercapto-3,9-dioxa-6-thiaoundene, bis (-mercapto Ethoxy) methane, bis (-mercaptoethylthio) methane, ethanedithio-1,2, propanedithiol-1,2, butanedithiol 1,4,3,4-dimercaptobutano
  • Suitable organic mercaptans are butyl mercaptan, butyl mercaptan, butyryl merbutane, lauryl mercaptan, mercaptoethanol, mercaptobrono, nol, mercaptoethanol, mercaptobutanol, mercaptobutanol, mercapto tungstic acid, mercaptobutrionic. Acids, benzyl mercaptan, phenyl mercaptan and the like, and in particular, lauryl mercaptan, mercaptoethanol, mercaptopropanol, mercaptobutanol, mercaptoacetic acid, and merbutobrovionic acid are preferable.
  • the content of the organic mercaptan per soluble copolymer is preferably 0.03 to 2% by weight in terms of the S content. If the content is more than 2% by weight, the sedimentation stability of the dispersion liquid is reduced, which is not preferable. , And less than 0.03% by mass If the content is too small, the dilution stability of the dispersion and the background contamination of the developed product are not preferred.
  • Soluble copolymers The monomer of the formula ( ⁇ ), the monomer of the formula ( ⁇ ⁇ ) and components other than the organic mercaptan are adversely affected by various properties such as stability, background fouling and surface printing. Can be contained as necessary within a range that does not affect
  • the soluble polymer used in the present invention is preferably 500,000 or less, more preferably 3,000 to 30,000, and most preferably 5,000 to 25,000. It has a molecular weight of 0. If the molecular weight is more than 50, 000, the dispersion stability is diminished or the developer tends to stain, which is not preferable. If the molecular weight is too low, the dispersion is too low. It is not preferable because the stability of the rubber becomes poor.
  • the ratio of the soluble copolymer (B) to the insoluble polymer (A) in the resin dispersion of the present invention is not particularly limited, but the soluble copolymer is preferably 5 to 50% by weight, more preferably 20 to 50% by weight, more preferably 30 to 40% by weight, and insoluble polymer 35 to 50% by weight, preferably 80 to 50% by weight, and more preferably 70 to 60% by weight. % Percentages are used. If the content of the soluble copolymer is less than 20% by weight, the stability of the resin dispersion is undesirably reduced. If the content is more than 50% by weight, the image is blurred or the density becomes low. In addition, it is not preferable that the printing durability is reduced.
  • the particle size distribution of the dispersed particles of the resin dispersion of the present invention is such that 70% or less, preferably S 0% or more, of particles having a size of 0.5 # or less.
  • the insulating hydrocarbon medium contained in the resin dispersion of the present invention has a low dielectric constant.
  • an electrically insulating organic solvent examples include normal paraffinic hydrocarbons, isobaraffin yarn hydrocarbons, aromatic hydrocarbons, and halogenated aliphatic hydrocarbons.
  • a paraffinic or alicyclic hydrocarbon-based medium having a boiling point of 150 to 200 is preferably used in view of odor, safety, drying property and the like.
  • the resin dispersion of the present invention can be easily produced by polymerizing an insoluble polymer in a solution of a soluble polymer in a medium, but a soluble copolymer and an insoluble polymer are separately prepared. It is also possible to suitably produce the compound by dissolving both polymers in a common solvent of both polymers, and then dropping the mixture in a hydrocarbon medium with stirring.
  • the particle size distribution of the resin dispersion can be adjusted by may varying the proportion of soluble copolymer insoluble polymers, also C [1-2 of the c) insoluble polymer. It can also be adjusted by changing the amount of the alkyl meta acrylate or acrylate.
  • the monomer of the formula (I) contained in the insoluble polymer In order to convert at least a part of the monomer of the formula (I) contained in the insoluble polymer into a quaternary ammonium, it is necessary to prepare a resin dispersion liquid and then use a sensitized ammonium salt such as dimethyl sulfate.
  • the monomer (I) may be ammoniated by a conventional method such as dimethyl sulfate or methyl chloride prior to the polymerization reaction as described above. .
  • the dispersion particles may be colored and charged as necessary.
  • a charge inhibitor In order to impart a charge to the resin dispersion of the present invention, a charge inhibitor is used, examples of such charge control agents include zinc naphthenate, manganese naphthenate, oleic acid, cobalt octoate, lecithin, sodium dioctyl sulfosuccinate, and aluminum stevelite rosin.
  • a grossine dye / phthalocyanine pigment oil black, carbon black or the like is used.
  • n-heptane-Og was added, and the mixture was refluxed with vinyl acetate: a mixture of I5Os and n-methyloctyl methacrylate, 25 g, and benzoyl peroxide, 4 s, was added in 2 hours. 1 50 g, a mixture of 40 s of n-heptane and 4 s of benzoyl peroxide was added dropwise over 1 hour, and the mixture was allowed to evaporate for 30 min. Add the mixture of Le Is and add 30 g of the mixture of Paryl L Is and 5 g of n-heptane.Add 1.5 g of the mixture, add Isobar G 13 Og and cool to 10 or less. Further, 0.1 lg of ethyl chloride was added. The resulting dispersion was a very stable, slightly translucent, slightly yellowish emulsion.
  • the mixture was kneaded for 24 hours to obtain a concentrated developer.
  • This concentrated developer with Isopar G A 10-fold dilution was used as a developer.
  • Example 1 The reactor of Example 1 was charged with 140 s of 2-ethylhexyl methacrylate, 60 parts of benzyl methacrylate, 0.4 g of azobisisobutymouth-tolyl, 3 g of mercaptoacetic acid and 358 of n-hexane. Heated until flowing. After refluxing for 2 hours under the reflux condition, a mixture of 10 g of toluene and 0.3 s of azobisisopti-tol-tolyl 0.3 s was added dropwise in 2 hours, and the mixture was further reacted for 2 hours to obtain a copolymer solution having a molecular weight of about 11,000. Obtained.
  • the resulting dispersion was a slightly transparent, pale brown emulsion having an average particle size of 0.2 m.
  • a mixture of 5 g of oil black HBB and xylene 208 was added dropwise to 100 s of the resulting resin dispersion liquid and 150 g of Isobar G with stirring, and aluminum stearate Is was added, followed by 10 addition of Isobar G to prepare a developer.
  • N-octyl methacrylate obtained according to Example 2 and cyclohexylmethacrylate 70 g of n-hexane, 130 g of Isopar G, 27 g of vinyl nitrate, 35 g of n-octyl methacrylate, 35 s of cyclohexyl methacrylate 2 lg and benzoyl peroxide 6 s were added, and the mixture was reverted under the flow of S. After 3 hours, whitening occurred. Further, a mixed solution of 45 g of n-heptane and benzoyl peroxide 28 was added and reacted for 1 hour.
  • a developer was prepared in the same manner as in Example 1 except that stearyl methacrylate was used instead of cyclohexyl methacrylate in Example 1. Comparative Example 2
  • a developer was prepared in the same manner as in Example 1, except that a mixture of 12 g of getylaminoethyl methacrylate, 4 g of n-heptane, and parlor L 1 s was not added when the dispersion was polymerized. .
  • a developer was prepared in the same manner as in Example 2, except that the amount of methyl sulfate after dispersion polymerization was changed from 0.1 g to 1 g.
  • a developer was prepared in the same manner as in Example 3, except that No addition of methyl was made.
  • compositions of the resin dispersions obtained in Examples 1 to 4 and Comparative Examples 1 to 4 are shown in Table 1, and the results of the printing test are shown in Table 2.
  • Soluble copolymer component (% by weight) Organic mercaptan Soluble copolymer component 1 ⁇ —
  • Example 1 As standard (3), the number was increased as the concentration increased.
  • the printability was evaluated based on the density of the printing paper obtained by the printability test, the bleeding at the edges of the image area, and the sharpness of the fine spots.
  • the printing test using the developer obtained here is as follows. Degree 4, bleed 4, it printability 4, clarity 5, background dirt 4,
  • the electrophotographic liquid developer for offset master which uses the resin dispersion of the present invention extremely, is diluted about 160 times to obtain a developing margin. Is extremely stable and does not cause development such as generation of a large amount of sediment or gel-like aggregates. There is no bleeding (blur of the outline) or background smear when performing offset printing, and 5,000 times The excellent clear image can be obtained even after printing It has face printability.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Liquid Developers In Electrophotography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Dispersion de résine appropriée en tant que révélateur liquide electrophotographique pour originaux offset, contenant dans un véhicule hydrocarbure hautement isolant (A) un copolymère essentiellement insoluble dans ledit véhicule et contenant (i) entre 20 et 99,5 % en poids d'acétate de vinyle, (ii) entre 0,5 et 12 % en poids d'un monomère représenté par la formule (I) (où R représente (IV), R1, R2, et R4 représentent chacun indépendamment hydrogène, alkyle comportant de 1 à 6 atomes de C, ou alkoxyalkyle contenant de 1 à 4 atomes de carbone dans chaque moitié alkyle, R3 et R'3 représentent chacun indépendamment un alkylène comportant de 1 à 4 atomes de C, et X représentent hydrogène ou méthyle), et (iii) entre 0 et 79,5 % en poids d'alkyle ester comportant de 1 à 20 atomes de C et/ou de cycloalkyle ester comportant entre 3 et 8 atomes de C d'un acide acrylique ou méthacrylique (à condition que la somme de (i), (ii), et (iii) soit égale à 100 % en poids), au moins une partie dudit monomère (I) étant quaternisée dans son groupe amino à l'aide d'un agent de quaternisation; et (B) un copolymère essentiellement soluble dans ledit véhicule et contenant (iv) entre 95 et 15 % en poids d'un monomère de formule (II) (où X est tel qu'il a été défini dessus, Y représente -COOR5, -OCOR5 ou -OR5 et R5 représente un alkyle comportant de 4 à 20 atomes de C), (v) de 5 à 85% en poids d'un monomère de formule (III) (où X est tel qu'il a été défini ci-dessus, et R6 représente un cycloalkyle comportant de 3 à 8 atomes de C ou un aralkyle contenant de 1 à 3 atomes de carbone dans la moitié alkyle) (à condition que la somme de (iv) et (v) soit égale à 100 % en poids), et (vi) de 0 à 2 % en poids (par rapport à la teneur en soufre) d'un mercaptan organique possédant au moins un groupe thiol (à condition que la teneur en soufre soit représentée en poids par rapport à une teneur en soufre relative au copolymère soluble).
PCT/JP1986/000333 1985-07-01 1986-06-30 Dispersion de resine WO1987000308A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP60/142565 1985-07-01
JP60142565A JPS625258A (ja) 1985-07-01 1985-07-01 樹脂分散液

Publications (1)

Publication Number Publication Date
WO1987000308A1 true WO1987000308A1 (fr) 1987-01-15

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ID=15318282

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1986/000333 WO1987000308A1 (fr) 1985-07-01 1986-06-30 Dispersion de resine

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EP (1) EP0227840A4 (fr)
JP (1) JPS625258A (fr)
WO (1) WO1987000308A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6490938A (en) * 1987-10-01 1989-04-10 Ohbayashi Corp Ventilating apparatus for building
JPH0331237U (fr) * 1989-08-01 1991-03-27

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1563240A (en) * 1976-10-27 1980-03-19 Hunt Chem Corp Philip A Liquid electrostatorgraphic toners
US4229513A (en) * 1979-05-29 1980-10-21 Eastman Kodak Company Liquid electrographic developers containing polymeric quaternary salts

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0227840A4 *

Also Published As

Publication number Publication date
EP0227840A1 (fr) 1987-07-08
EP0227840A4 (fr) 1988-05-31
JPH0584515B2 (fr) 1993-12-02
JPS625258A (ja) 1987-01-12

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