DE2020839A1 - Liquid developer for electrostatic photography - Google Patents

Description

Kabushiki Kaisha Ricoh 2 8. ApHS B7Ö

Tokyo, Japan Liquid developer for electrostatic photography

The invention relates to a liquid developer for electrostatic Photography, with which you can have an electrostatic Can develop latent image in the form of a dispersion very fine particles of a special, dye-like polymer in a carrier liquid. The term "electrostatic Photography "in the sense of the invention includes technology the development of an electrostatic latent image produced by exposure of either the photosensitive surface of a copy material for black and white or color electrophotography or an electrostatic recording paper after or without being (soft) charged beforehand (uncharged). With the term "dye-like Polymer ", on the other hand, is a polymerisation product of a pigment or dye with one reactable with it Meant connection. -

The previously common liquid developers for electrostatic Photographs were made by looking at the surfaces of pigment or dye particles Adsorption or other adhesion with a resin, oil and the * the same coating, which was able to regulate polarity and stabilize dispersion at the same time, and the one obtained in this way Toner dispersed in a carrier liquid of high insulation resistance and low dielectric constant. Plants are suitable as resin or oil components *

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109886/1517

resin, hydride vegetable resin, e.g. in the form of the commercial product "Stebelite", linseed oil, alkyd resin, styrene resin, phenol modified Resin, acrylic resin, synthetic rubber, ethy! Cellulose and the same. Such a resin or oil is required to give the toner particles a pronounced, positive or negative polarity to grant and to ensure their uniform dispersion in the carrier liquid »Such a toner will corresponding to the electrostatic latent image charge on the photosensitive surface during the development process fixes and thereby delivers the desired copy of the image. The toners contained in the liquid developers commonly used up to now but possessed the imperfection that it was done in the first time after. Production comparatively pronounced However, polarity and good dispersion showed on the resin or dye particles (both together below always briefly referred to as dye particles) adsorbed Resin gradually passed or diffused into the carrier liquid over time, resulting in clarity and precipitation or coagulation and thereby further deteriorated fixing performance and fuzzy training Image copies led. In order to avoid such a resin separation, liquid developers have already been created whose toners are made from chemically bonded with reactive compounds, for example condensed with vinyl compounds or graft-polymerized dye particles. In addition, these previously common toners had comparatively coarse particle size and low transparency, which made them particularly unsuitable for multicolor electrophotographs, well as a result of the color set correspondingly selective light wave absorption and reflection for the partial colors magenta, cyan or yellow impaired and thus insufficient color balance as well as deteriorated resolving power and

109886/1517

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this ultimately resulted in a lack of fidelity to the original of the color image copy.

The invention now aims to create a positive or negatively charged positive developer for electrophotography, which is free from these disadvantages and either the composition 1) or the composition 2) described below Type has

1. The liquid developer for electrophotography with in a carrier liquid of high insulation resistance and low dielectric constant uniformly distributed, negatively charged, dye-like polymer particles is characterized in that these polymer particles from the chemical reaction product between a reactive dye, i.e. one with a reactive, functional residue, and a mixing component consist of a compound according to of the general formula 2)

in the X ₁ -COCl, -CONH ₂ , -

_{n2ri + 12} with η equal to one of the integers 1 to 8, / ^ Vi

with η equal to 1 or 2, -CON. with R equal to (H> * - * τ *

with η equal to one of the integers

109886/1517

-COOC _n H _2n "" N (C _n I Hg _n I ₊₁ J ₂ ^mi * ⁿ S ^leicn one of the

- - Integers 2 to 5 and

N (C ₁₁₁ H _2n , ₊₁ ) _{3 n} , _{equal to one of the}

H Γ integers 1 to 8

-COO-N ⁺ (CnH _{2n + 1} OH) ₃ with ή equal to 1 or 2

and Y ₁ denotes a hydrogen atom, the methyl radical or a chlorine atom, and a compound of the general formula 1)

CH ₂ = C
X

in which X -COOC _n H _{2n + 1} , OCOC _n H _{2n + 1} , OC

⁰¹ WWl «» ^{w 0} ^ ⁰⁰ AnH ^{with n}

one of the integers 7 to 16

and Y is a hydrogen atom or the methyl radical mean in the molar ratio range between the two of 0.1 to 9.9 to 3 to 7.

2. The liquid developer for electrophotography with a carrier liquid of high insulation resistance and low dielectric constant uniformly distributed, ligatively-charged, dye-like pigment particles is characterized by the fact that this pigment

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particles from the chemical reaction product between a reactive dye, i.e. one with a reactive, functional group, and a mixed component consist of a compound of the general formula 3)

Ϊ ²

Inder X ₂ -COOC ₂ H ₄ OH, -OCH ₂ CH ₂ OH

-COOH; -CH -CH ₂ ; -COOCH ₂ GH - CH ₂ ; 0 0

-CO-CH ₀ -CH = CH ₀ .; -CH -0-CH ₀ -CH-CH ₀ ; Il ^{2 2} 2 2 \ / 2

0 ■ '0

-CH-CH ₂ -O-CH ₂ CH ₂ -Ch-CH ₂ ; - ^ VCOÖCH CH-CH;

V V

Op ', - (V. OH

and Y ₂ denotes a hydrogen atom or the methyl radical, and a compound of the general formula 1) explained above exists in the molar ratio range between the two from 1: 4 to 2: 5.

0886 / 1S 1 1

Paraffin-containing polymers are and are known per se as a pigment for inks, printing inks, paints and dyes for coloring high molecular weight material, fibers and the like are used. They are produced in such a way that either a dye is chemically attached to a reactive one Compound binds or a polymer containing amino residues first dlazotiert and then coupled with a coupler. Dye-like polymers produced in this way are suitable but not for electrostatic photography because, firstly, they are not in the carrier liquids required for this Liquid developers, such as η-hexane, n-heptane or the like, are dispersible and, secondly, not the polarity present that for the generation of a fast electrophoresis according to the charge distribution (or the lines of force) sufficient in the electrostatic latent image

In contrast to this, the dye-like polymers used according to the invention are free from these disadvantageous properties. Since they contain a formula 1) compound in the form of a vinyl compound with a strong affinity for the carrier liquid and a compound either according to formula 2) or according to formula J) in the form of a vinyl compound with a functional residue that is able to charge the polymer particles negatively or positively, the properties of the individual components can be revealed through the joint binding of these two types of compounds © n reactive dye-material particles. More precisely, the formula 1) contains the X radical in the form of a long-chain alkyl radical with a strong affinity for the carrier liquid, while at the same time the Y ^ radical in the formula 2) compound or the Y ₂ radical in the formula 3) ^ 'Compound ensures that the dye-like polymer in

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the carrier liquid its pronounced negative (in the formula 2) case) or positive (in formula J) -FaIl) polarity is maintained.

Below are some specific examples of such Formula 1), 2) or 3) compounds are listed. The Formula 1) compounds include, for example:

Hexyl acrylate, lauryl methacrylate, stearyl acrylate, octyl methacrylate, Tridecyl acrylate, pentadecyl methacrylate, hexadecyl methacrylate, 2-ethylhexyl methacrylate, vinyl hexylate, Vinyl stearate, vinyl octylate, vinyl tetradecylate, Vinyl hexadecylate, vinyl heptalate, hexyl vinyl ether, 2-ethylhexyl vinyl ether, Stearyl vinyl ether, tridecyl vinyl ether, hexadecyl vinyl ether, allyl hexylate, allyl laurylate, allyl stearate. Allyl hexadecylate. Allyl tetradylate, acrylootylate, Witches, pentene, cones, dodecene, hexadecylene, Tridecylene, octene or mixtures thereof.

The formula 2) compounds include, for example, j

Dimethylaminoethyl methacrylate, dibutylaminoethyl methacrylate, Dioctylaminohexyl acrylate, acrylamide, dimethylacrylamide, Dibuty! Acrylamide "dioctylacrylamide, methylacrylamide, Dibutyl acrylamide, dioctylacrylamide, methyl acrylamide, dibutyl acrylamide, dioctylacrylamide, methylacrylamide, Ethyl acrylamide, butyl acrylamide, cyclohexyl acrylamide, Phenyl acrylamide, benzyl acrylamide, 2-chloroethyl methacrylate, p-chlorostyrene, p-aminostyrene, o-aminostyrene, p-methylaminostyrene, 2-vinylpyridine, 4-vinylpyridine, p-acetamidostyrene, p-acetdimethylaminostyrene, p-acetoctylaminostyrene, Trimethylaminoacrylate, triethanolaminoacrylate, Trioctylamino acrylate or mixtures thereof.

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The Formula 3) compounds include, for example:

2,3-epoxypropyl acrylate, hydroxyethyl methacrylate, 2,3-epoxypropyl methacrylate, Allyl methacrylate, allyl alcohol, butadiene oxide, acrylic acid, acrylic glycidyl ether, glyoidyl p-vinyl benzoate, 2-methyl-5,6-epoxy-1-hexene, p-nitrostyrene, vinyl benzoic acid, o-nitrostyrene, p-hydroxystyrene or Mixtures of the same

W Any compound that chemically couples with the formula l) -3) compounds explained above is suitable as a reactive dye -1-anthrachlnonylamino) -1,3,5-triazine, 2,6-diehlor-p-phenylenedlamine and the like, use, the amino radical contained in them being diazotized before coupling.

Some specific examples of such reactive dyes useful in the present invention are given below enumerated *

Ί09886 / 15 17

Yellow dye

OH

OH

SO ₅ Well

Red dyes ? ^H 5

H CH

C ₆ H ₅

H ₂ N

CH ₃ OH

SO ₃ Na OH

OH

³ SO ₃ Na

H ₂ N

SO ₃ Na

CH ₃

NH,

OH

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Blue dye

) ₂ ci

NH ₀ ,

COONa

NH

3H ₅ CO-

SO ₅ Na NH ₂ OH

NH,

SO ₅ Well

OCH

[^ fV-N = N-

^ H

)H

^ ™

NH

S0, well

NHCOCH,

Black dye

SO,

SO, well

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The synthesis of the dye-like polymers used according to the invention is carried out with a non-ionic surfactant, such as ζ.Β · polyethylene glycol monolaurate, polyethylene glycol monostearate, polyoxyethylene oleyl ether, polyoxyethylene cetyl ether. Polyoxyethylene alkyl allyl ether, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan monolaurate. Sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate or sorbitan trioleate, of which about 0.1 to 2 %, based on the total weight of all materials used, are used.

As already explained in connection with the identification of the invention, dye-like polymers are created with negative ones Polarity by combining a formula I) - and a formula 2) connection and those with positive polarity through Combination of a formula I) and a formula 3) compound in the molar ratio range given for each combination, gives the mixture a previously diazotized in a conventional manner Add dye and heat everything together, preferably in Presence of a catalyst at 30 ° for 1 to 10 hours up to 100 ° C.

The coupling of the vinyl compound mixture with the dye takes place via the diazo residue according to the following, probable Reaction scheme:

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^ la20ti SatIo

COOCH

CH-

1 -

H ₂ C - / CH ₃ \

00CH:

CH;

CH.

dOOCH,

CH-

CH ₂ = C

COOCH ₂ CH ₂ N (CHj);

/ Γ ³ - \ / Γ ³

Ic. f-c "

ν COOCH ₃ / m \ COOCH ₂ CH ₂ N (CH ₃ ) ₂ / η

About 10 to 30% of the reactive dyestuff is usually taken based on the weight of the compound mixture mentioned. Compound mixture is about 20 to 50 % and in the case of the formula 1) + formula 3) compound mixture is about 20 to around 4 % . The reaction-accelerating catalysts include compounds of the general formula

" Ri

0OR

in which Z is a hydrogen atom or the methyl radical and R is the C _n H _{2n + 1} radical with η being 1, 2, 3 or 4,

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including methyl methacrylate, ethyl methacrylate, acrylonitrile, butyl methacrylate, methacrylate acrylate or the like.

The liquid developer according to the invention is reproduced usual way of working by first doing the above described type obtained, dye-like polymer dispersed in a medium such as toluene and the thus obtained, concentrated toner with an appropriate amount of a carrier liquid having a resistivity greater than 1O ^ ohms. cm diluted, as it is usual for common liquid developers.These include η-hexane, n-heptane (e.g. in the form of the commercial product Shellsol from Esso Standard Oil Co.), ligroin, petroleum hydrocarbons (e.g. in the form of Esso commercial products Naphtha No 6, Solvesso 100, Isopar H, Q, L and the like) and the like.

The dispersed in the liquid developer according to the invention Toner particles have an extremely fine grain size of only about 0.01 to 0.1 / U, so that they pass through the densest filter paper (of 0.25 / U pore size) run through it. The polymer forming the toner is also so chemically solid with the dyes often associated with particles that no precipitation or coagulation occurs, as is the case with the usual developers as a result of the Resin or oil separation is unavoidable. By doing this, stay uniform over long periods of more than a year Maintained dispersibility and pronounced polarity. the The excessively fine grain size of the toner particles also gives the Another advantage that the electrostatically generated copy has a high resolution and is independent of the That is, the type of charge is free of edge effects without such charge or with only a soft charge or the like, and

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furthermore in connection with the high particle transparency Particularly in the case of electro-color photography, a selective absorption and reflection of the white light guarantees "which also the color laws of the three partial colors is true, so that the final multicolor copy is of high quality in terms of color balance and fidelity to the original

The invention is explained in more detail below with the aid of a few exemplary embodiments, without being restricted to them.

example 1 Preparation of a blue dye-like polymer

A suspension of 3.5 g of finely divided tetra-4-aminocopper phthalooyanine in 40 ml of water was first prepared and a mixture of 4j, 4 g of concentrated hydrochloric acid and 40 ml of water was added to it. Furthermore, a mixture of 8 g of ice and an aqueous solution of 1.6 g of sodium nitrite was prepared. The hydrochloric acid solution was then ^{stirred for 30 minutes at 0} to 5 ° C., all of the nitrite solution was added at the same temperature and the mixture was stirred for a further 15 minutes. The so diazotized, aqueous solution was then added to an emulsion of 5 g of methyl methacrylate, 10 g of lauryl methacrylate, 1 g of dimethylaminoethyl methacrylate together with 1.0g Polyoxyäthylensorbitanmonostearat (as a surfactant) in 30 ml of water and mixed with heating at up to 6o ° to 70 ⁰ C. Subjected to polymerization for 2 hours. After the polymerization had taken place, the solution was extracted with 500 ml of toluene, and 450 ml of toluene were evaporated from the extract. The extract residue was poured into 200 ml of methanol and gave a methanol-insoluble, highly viscous, bluish-purple resin substance, which by redissolving in 50 ml of toluene · and

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Reprecipitation was purified with methanol.

A ready-to-use blue dye was obtained in this way in a yield of 7.5 g Polymer that exhibited excellent transparency and dispersibility and a polarity with pronounced negative charge.

Example 2

Preparation of a blue dye-like polymer |

First, an emulsion of 5 g of methyl methacrylate, 15 g of lauryl methacrylate and 3 g of hydroxylethyl methacrylate in 30 nil of water was prepared with the aid of Ig polyethylene glycol monostearate. The emulsion obtained in this way was mixed with a solution diazotized according to Example 1, stirred for about 2 hours with heating to up to 60 ° to 70 ° C., cooled and extracted with 500 ml of toluene. The extract were removed from 450 ml of toluene and the residual liquid was poured into 200 ml methanol to give a blue-colored resin substance separated out, by three times repeatedly dissolving in 50 ml of toluene and re-precipitation with 200 ml of methanol and schliessliches drying overall m cleans was . .

A polymer was obtained in a yield of 11.5 g, which showed excellent transparency and dispersibility and a polarity with a vivid positive charge exhibited.

Example .. 3

Production of a yellow dye-colored polymer

5 g of 2,4,6-tris (4-amino-l-inthraquinonylaniino) -l, 3,5-s- triazine were dissolved in 150 g of concentrated hydrochloric acid | «± 8e8«, ^er *

103886/15 1 7> 16 -

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was added at ⁰ C in one portion with a solution of 1.7 g of sodium nitrite in 8.5 ml water and 30 minutes diazotized at about 0 ° to about 2 ° C. The resulting diazo solution was treated with sulfamic acid in order to remove excess sodium nitrite and filtered. An emulsion was added to the clear solution which, by adding 1 g of polyoxyethylene oleyl ether (as a nonionic surfactant) to a solution of 10 g of lauryl methacrylate, 5 g of dimethyl methacrylate and 1 g of p was -Aminostyrol in 30 ml of water is manufactured _ and the total mixture was fully reacted under general ™ mählicher temperature increase to 8o ° C to about 90 ⁰ C for 2 hours. The reaction solution thus obtained was extracted with 500 ml of toluene. 450 ml of toluene were evaporated from the extract and the remaining solution was mixed with 200 ml of methanol, a yellow resin substance separating out, which was purified by dissolving it three times in 50 ml of toluene each time and reprecipitating it with 200 ml of methanol each time.

A polymer was obtained in a yield of 13.5 g, which showed excellent transparency and dispersibility and a polarity with a vivid negative charge ^ exhibited.

Example 4 Production of a polymer ready for yellow dye

The diazotized aqueous solution obtained according to Example 3 was a mixture of 10 g of lauryl methacrylate, 5 g of ethyl acrylate, 3 g of glycidyl methacrylate and 30 ml of water were added and by adding 1 g of the surfactant mentioned in Example 3

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emulsified. The emulsion thus obtained was allowed under gradual increase of temperature up to 8o ° C to about 90 ⁰ C to react for another 2 hours. As in Example 5, the yellow-colored polymer was again deposited from the fully reacted solution and purified.

A polymer which showed excellent transparency and dispersibility was obtained in a yield of 1 g had a polarity with a vivid, positive charge. The color transparency of an image copy made with it was very good·

Example β

Production of a red dye-type polymer

4.7 g of a dye which had been obtained by diazotizing 2,6 dichloro-p-phenylenediamine and coupling the diazo compound with 3-C-kynaphthoic acid-m-aminoanilide was suspended in 35 g of concentrated hydrochloric acid and thus suspended diazotized by adding 1.6 g of sodium nitrite. In the thus obtained Piazolösung 15 g of lauryl methacrylate, well stirred in 5 g of butyl methacrylate, 2 g of vinyl benzoate and 30 ml of water, and the polymerization was continued while slowly increasing the temperature to 8o ° C to about 90 ⁰ C for 2 hours. The polymerization product, a yellow resin substance, was deposited as in Example 3 and purified.

A polymer was obtained in this way in a yield of 12.5% which showed excellent transparency and dispersibility and a polarity with a vivid negative charge exhibited. The color transparency of one made with it

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- Io image copy was very good.

Example 6 Production of a red dye-like polymer

A mixture of 15 g of lauryl methacrylate, 5 g of methyl methacrylate, 2.5 g of allyl methacrylate and 30 ml of water was emulsified as a nonionic surfactant with the addition of 1 g of sorbitan monolaurate. The emulsion thus obtained was made with the geaäss P Example 5, diazotized aqueous solution are mixed, with gradual temperature increase to 8o ° stirred for 2 hours to about 90 ⁰ C and worked up by cooling in the direction indicated in previous examples manner to the cleaned red colored polymer.

In this way, a polymer was obtained in a yield of 9.5 g which had excellent dispersibility and was lively was able to deliver negatively charged dispersion. A hot image copy made with it had superior transparency.

The dye types obtained according to the above examples Gen polymers were used to produce liquid developers for electrophotography by initially applying Knead with a dispersant to form a concentrated toner, and then this in the final Carrier liquid was suspended.

About the composition of this liquid developer gives the Table I below for information.

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Table I. Dye-like polymer dispersant carrier liquid

Pure product of

Example 1 5 g Naphtha No 6 50 g Isopar H 1000 ml

Pure product of naphtha

Example 2 5 g η-hexane 4og No 6 1000 ml

Pure product of "

Example 3 5g SHELLSOL 40g Isopar G 1000ml

Pure product of naphtha

Example 4 7.5g Ligroin 50g No 6 +

Isopar H 1000ml (in the ratio 4: 6)

Pure product of

Example 5 5g n-heptane, 45g Solvesso +

Isopar H 1000ml (in the ratio 3: 6)

Pure product of naphtha Νοβ +

Example 6 7g Isopar H 50g Isopar H 1000ml

(in a ratio of 7: 3)

These six liquid developers have those in the following
Properties given in Table II on:

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Tabel. II

Liquid developer
according to
example

Stabilizing effect on

polarity

Fine grain size of the toner

Dispersion

polarity

1 negative <0.25 / rev 2 positive <0.25 _/ U 3 negative <0.25 _/ U 4th positive <0.2 _{5 /} u 5 positive <0.25 / rev 6th positive <0.25 / rev

No precipitation at
15,000 rpm

No change in the course of more than 1 year

The performance test was carried out in such a way that the
Zinc oxide and the quater polymer of styrene-butyl methacrylate-glyeidyl methacrylate «acrylic acid in a molar ratio of 60O2; 5: 3
existing, photosensitive layer of a copier material first charged with -6KV corona discharge, provided with an electrostatic latent image by exposure and
the latter developed with a developer of the type described above; became. A clear, positive or negative color copy was obtained in each case. When the copy material

1 U 9 8 8 6/1 b 1 7

BATH ORIGINAL

one after the other - each time recharging and developing - with the partial color separations of a multi-color original exposed and treated with the developers in the order of Examples 4, 2 and 5, a clear one was obtained Multicolor image copy.

Example 7 -

In the same way as in the earlier examples, a majority of dye-like polymers were prepared from the following The dye and vinyl compound components listed in Table III below manufactured. Each 1 part by weight of this was mixed with 2 to about 10 parts by weight of naphtha No. 6 to a concentrated toner, kneaded and each of these became one in each 1,000 ml of Isopar H as a carrier liquid dispersed liquid developer according to the invention. All liquid developers obtained in this way showed the same favorable properties as the developers achieved in previous examples and possessed each also in Table III specified polarity.

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Table III

dye vinyl compound to be converted 15 g
2 g
5 g polarity Hexadecyl methacrylate
4-vinyl pyridine
Methyl methacrylate 25 g
35 g negative Vinyl hexyl acrylate
p-nitrostyrene 20 g
25 g
8 g positive Tetra-4-amino
copper phthalo-
cyanine
5 g Allyl tetradecylate
o-aminostyrene
Butyl acrylate 10 g
5 g
3 g
5 g
15 g negative 1-octene
Styrene
Benzyl acrylamide
Butyl methacrylate
Tridecyl vinyl ether 8 g
25 g
10 g negative Acrylic glycidyl ethers
Hexyl methacrylate
Acrylonitrile 20 g
8 g
10 g positive Oc tyl acrylate
2,3-epoxy propylene ethylate
Methaerylate positive

109Ö86 / 1517

2,4,6-Trl- (4-amino-l- anthraquinonylamino) -l, j5,5,6- triazine

10 g

Hexyl acrylate 50 β

Dibutylaminoethyl

methacrylate Ig

Ethyl methacrylate 5 g

Vinyl hexylate 60 g

pimethylacrylamide 5 g

Methacrylate 2Og

Allyl hexadecylate ^ 5 g

Triethanoiamino aerylate 5 g Butyl acrylate, 1-5 g

Allyl laurylate

2-methyl-5,6-epoxy ether 10g Vinyl hexadecylate 10g

Methacrylate 21g

1-hexen 20 g

p-nitrostyrene 5 g

Heptadecyl methacrylate 30 g

Methyl methacrylate 20 g

negative

negative

negative

positive positive

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C / 1 5-1-

BATH ORIGINAL

2Q20839

Vinyl hexadecylate 35 g p-vinyl benzoic acid 2.5 g _positive glyeidylhexyl methacrylate 2.5 g butyl methacrylate 15 g

2,6-dichloro-p-

phenylenediamine

fi -oxynaphthic acid-

m-aminochloride

G

Allyl hexylate Benzyl acrylamide methacrylate

60 g 6 g 18 g

Vinyl octylate 50 g

Acrylic acid 15 g

2,3-epoxy methacrylate 5 g

Methacrylate 18 g

negative

Hexadecylene 40 g p-dimethylaminostyrene 5 g

2-ethylhexyl methacrylate 15 g ^ne e ^afciv

Butyl methacrylate 20 g

negative

Vinyl hexadecylate 30 g

2-chloroethyl methacrylate 3.5g

Dioctylaminohexyl negative

methacrylate 3 g

Butyl acrylate 15 g

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Claims (3)

Kabushiki Kaisha Ricoh
Tokyo, Japan P ate η t a η s ρ r ü c he Liquid developer for electrophotography in one Carrier liquid with high insulation resistance and low dielectric constant dispersed toner particles, characterized in that the toner consists of a dye-like polymer in the form of the chemical Binding product between a dye, the one having reactive, functional radical, and one Mixing component consists, on the one hand, of a compound of the general formula 1) = C in the X-COOC _n H _{2n + 1} , -OCOC _n H _{2n + 1} , -OC _n ^ n ¹ Wl '- ^ rftntl'' ^or "with η each equal to one of the integers 7 to 16 and Y is a hydrogen atom or the methyl radical mean" and on the other hand either from a compound of the general formula 2) . - 26 -10 9886/1517 in the X ₁ -COCl, -CONHg, COOCHgCHgCl, with η equal to one of the integers 1 to 8, Λ — V * halogen -NH ₂ - -9 W. / 2 ,. -ff -O-O- with η equal to 1 or 2, -CON ^ JJ with R equal or C _n H ₂ ^ with η equal to one of the integers 1 to 12, -COO-N ^ (C 1H _0. , U H *
-C0N (C _n , H _2n , ₊₁ ) ₂ where η is one of the integers 2 to 5 and n ¹ is one of the integers 1 to 8 H ₂ j ^ QH), where η is 1 or 2 and Y _{1 is} a hydrogen atom, the methyl radical or a chlorine atom,
or from a compound of the general formula J5) - 27 - 109886/1517 in which X ₂ -COOC ₂ H ₄ OH, -OCH ₂ CH ₂ OH, -C OOH, -CH CHo »'C 0OCH ₀ CH Ό ■. ■. 0 CO-CH ₂ -CH = CH ₂ , -CH ₂ -O-CH ₂ -CH-CH ₂ , 0 0 -CH-CH ₂ -O-CH ₂ CH ₂ -CH-Ch ₂ , -T ye 00CH ₂ CH-CH ₂ , 0 0 -CH ₂ -CH ₂ -CH-CH ₂ ,
0 and Υ «is a hydrogen atom or the methyl radical mean, where the molar ratio of formula 2) to formula 1) compound is between 0.1: 9.9 and 3: 7 and that of formula 3) - to formula 1) compound is between 1: 4 and 2: 3. 2) Liquid developer according to claim 1, characterized in that » that the reactive, functional residue in the dye consists of an amino residue. 3) liquid developer according to claim 1 or 2, characterized characterized in that the dye is present in the range of 10 to 30 percent by weight of the blend component is · - "'. ■' .-, ■ S 109886/1517 BATH ORIGINAL