DE2020839C3 - Electrophotographic suspension developer - Google Patents

Description

The invention relates to an electrophotographic A suspension developer comprising a toner which is a reaction product of a compound of the formula

20 -CH

or C _n H _{2n + 1} and η = an integer from 1 to 12 of the group

CH ₁ = C

(I)

25th

where X equals the group

-COOC _n H ₂ . _{+ 1} -OCOC _n H _{2n + 1}
- C "H ₂ " _{+ 1}

-OC _n H _3n

-CH ₂ OC _n H _2n

35

where η = an integer from 6 to 7 and Y is a hydrogen atom or a methyl group. and either a compound of the formula -COOC _n H _2n -N (C _n H _{2 n + I} ) ₂ -COO-N (C _n H _{2n + 1} ) J

H
-CON (C _n H _{2n + 1} I ₂

with η = an integer from 2 to 5 and η = an integer from 1 to 8 of the group

-COO-N (C _n H _{2n + 1} OH) ₃

CH ₁ = C

Y ₁

X ₁

_m j _t "₌; _oc j _cr _. _unc j Y _{1 g} i _e j. _: h eiiwm is a hydrogen _or chlorine atom or a methyl group. or a compound of the formula

(II)

wherein X _{1 is the} same as the group

-COCI -CONH ₁ COOCH ₁ CH ₁ CI

with /; = an integer from 1 to 8 of the group

* 5 CH ₁ = C

X ₂

wherein X _{2 is the} same as the group
5 °

-COOC ₂ H ₄ OH -OCH ₂ CH ₂ OH -

Λ / ^CH ' O
-COOCH ₂ CH CH ₂

(III)

55

NH,

60 O
CO-CH ₂ -CH = CH ₂

-CH-CH ₂ -O-CHjCH ₂ -CH, CH ₃

// V

COOCH ₁ CH CH ₂

CH ₂ - CH ₂ -CH ₂ CH

θ '

IO

NO ₂ or

> -ΟΗ

and Y _{2 is} equal to a hydrogen atom or a methyl group, the molar ratio of compound of formula II to compound of formula I between 0.1: 9.9 and 3: 7 and the molar ratio of compound of formula III to compound of formula I between 1: 4 and 2: 3.

The hitherto customary electrophotographic suspension developers for developing latent electrostatic Images are produced in such a way that pigment or dye particles are superficial with resins, oils and the like, which at the same time regulate polarity and have a dispersion-stabilizing effect, coated and the toner obtained in a carrier liquid dispersed by high insulation resistance and low dielectric constant. As resin or Oil components are vegetable resins, hydrogenated rosin, linseed oil, alkyd resins, styrene resins, phenol modified resin, acrylic resins, synthetic rubber, ethyl cellulose and the like. Such resins or oils are used to give the toner particles a pronounced positive or negative polarity and ensure their uniform dispersion in the carrier liquid. The toner particles contained in the known suspension developers are with the The disadvantage is that they have a relatively pronounced polarity in the first time after production has taken place show and form a perfect dispersion, but that on the pigment or dye particles adsorbed resin gradually passes into the carrier liquid over time, resulting in blurring polarity and precipitation or coagulation and consequently deteriorated Fusing performance and developing blurred image copies. In addition, they have known toner particles contained in electrophotographic suspension developers have a relatively large particle size and poor transparency, making them particularly unsuitable for multicolor electrophotography because it enables the selective absorption and reflection of light waves for the partial colors purple, Blue-green and yellow impaired and thus an insufficient color balance, a deteriorated resolving power, ultimately no lack of fidelity to the original of the color image copy and the like can be achieved.

The invention is based on the object of creating an electrophotographic suspension developer, the arbitrarily colored toner particles of which have a pronounced positive or negative polarity and are dispersion-unstable over a long period of time, and which mattes the production of multicolor copies.

The invention relates to an electrophotographic suspension developer of the type mentioned at the beginning Type which is characterized in that the toner consists of a reaction product of a dye or pigment with compounds of the formulas 1 and II or I and III.

Colored plastics are known per se and are used as pigments for inks, printing inks and paints and used as dyes for coloring high molecular materials, fibers and the like. One poses they are manufactured in such a way that one either chemically attaches a dye to a reactive compound binds or an amino group-containing polymer is first diazotized and then with a Coupler couples. Colored plastics produced in this way are not suitable as toners in electrophotographic Suspension developers because, firstly, they are not in the carrier liquids required for this. like η-hexane. n-Heptaii od. The like. Are dispersible and, secondly, do not have the polarity that to run a rapid electrophoresis according to the charge distribution (or the lines of force) in the electrostatic latent image to be developed is sufficient.

In contrast to this, the colored tools used in electrophotographic suspension developers according to the invention do not suffer from the disadvantages described. Since they contain a proportion of monomers of the formula 1 in the form of a vinyl compound with a strong affinity for the liquid carrier wedge and a proportion of monomers either of the formula II or of the formula III in the form of a vinyl compound with a functional radical that is able to charge the toner particles negatively or positively, the properties of the individual components can be used by binding these two types of compound together to reactive dye particles. Monomers of the formula I have as radical X a lar.ekettigen alkyl radical with a strong affinity for the carrier liquid, while at the same time the radical Y, in the case of the monomers of the formula II or: w. the radical Y ₂ in the case of the monomers of the formula III ensures that the colored plastic in the carrier liquid has a pronounced negative polarity - when using monomers of the formula II or positive - when using monomers of the formula III.

Some examples of compounds of the formula I are given below:

Acrylic acid hydroxyl ester.

Methacrylic acid lauryl ester.

Acrylic acid estcaryl ester,

MethaTyl acid octyl ester,

Acrylic acid tridecylcier.

Pentadyl methacrylate,

Methacrylic acid hexadecyl ester,

Methacrylic acid-2-ethylhexyl ester,

Vinyl caproate,

Vinyl stearate,

Caprylic acid vinyl ester,

Vinyl myristic ester,

Vinyl phenitate,

Vinyl heptanoate,

Hexyl vinyl ether,

2-ethylhexyl vinyl ether,

20th

Stearyl vinyl ether, tridecyl vinyl ether, hexadecyl vinyl ether, caproic acid allyl ester, Allyl laurate, allyl stearate, allyl palmitate, Allyl myristic acid, caprylic acid acrylic ester.

Witches.

Pen ten.

Nuns.

Dodecene,

Hexadecylene.

Tridecylene.

Octene or mixtures thereof.

The following are some examples of connections r Formula II called:

Dimethylaminoethyl methacrylate.

Methacrylsäuredibutylaminoäthyiester, Acrylsäuredioctylaminohexylcster, Acrylamide.

Dimethylacrylamide.

Dibutyl acrylamide, dioctyl acrylamide, methyl acrylamide.

Ethyl acrylamide, butyl acrylamide.

Cyclohexyl acrylamide, phenyl acrylamide, Benzylacrylamide, 2-chloroethyl methacrylate, p-chlorostyrene, p-aminostyrene.

c-aminostyrene.

p-dimethylaminostyrene, 2-vinyl pyridine.

4-vinyl pyridine.

p-Acetamidostyrene, p-Acetdimethylaminostyrene, p-Acetoctylaminostyrene, Trimethylaminoacrylate, triethanolaminoacrylate.

Trioctylamino acrylate or mixtures thereof.

The following are examples of door connections of sleeve III:

AGrylic acid ^ -epoxypropyl ester,

Hydroxyethyl methacrylate, 23-epoxypropyl methacrylate, Allyl methacrylate, allyl alcohol, butadiene oxide.

Acrylic acid,

Acrylic glycidyl ether, p-vinylbenzoic acid glycidyl ester, 2-methyl-5,6-epoxy-1-hexene, p-nitro-styrene, Vinylbenzoic acid, o-nitrostyrene, p-hydroxystyrene, or mixtures thereof.

To react with the monomers mentioned, all of them can be used in conjunction with these monomers Compounds incoming dyes, e.g. B.; tra - 4 - aminocopper phthalocyanine, 2,4,6 - Tn- - amino - 1 - anthraquinonylamino) - 1,3,5 - triazine.

2,4-dichloro-p-phenylenediamine and the like respective amino group diazotized before the reaction.

The following are dyes suitable for producing the colored toner of electrophotographic recording materials according to the invention specified.

Yellow dye

35

40

55

60 H ₂ N- <

-N = N

OH

H, N

-N = N-

Y \ _ _{N == N} _ CN = N- <
/ Red dye SO, N / A , N- CH ₃ CH CH ₃ -N (CH., C. 5 N = / ~ v -NH ₂ N-
I. Γ '
CH., C "H OH

CH ₁

H, N

OH SO ₃ Na

N = N

CH ₃

SO ₃ Na

SO ₃ Na

OH

H ₂ N

^CHj SO ₃ Na

409683/280

OH

H ₂ N ^ yN = N ₁ AA, SO ₂ NH-C ₆ H ₅ j

SO ₃ Na Η, Ν

CH ₃

—OSO ₂ -

OH

N = N-

SO ₃ Na SO ₃ Na

Blue dye

= N (C ₂ H ₅ ) ₂ C!

f V

-NH,

NH,

HO

COONa

N N

NH

SO ₃ Na

NH-

-NH,

CH ₃ CO-NH

SO ₃ Na

OCH,

, S- ' _VN ) -NH ₂

OH

NH,

N = N

\ ^ - ° ^Η CH ₃

SO ₃ Na

N = N

N N

NH

NHCOCH,

Black dye
SO ₃ Na OH

• SO ₃ Na

In making the in electrophotographic

disengaged from pension developers according to the invention, colored toners are non-ionic, super-

surface-active substances, such as B. Polyethylene glycol mono- »Urate, polyethylene glycol monostearate, polyoxyethylene oleyl ether, polyoxyethylene acetyl ether, polyoxy-

ethylene alkyl allyl ether, polyoxyethylene sorbitan monostearate, Polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan monolaurate, sorbitan monolaurate, Sorbitan monopalmitate, sorbitan monoslearate or sorbitan trioleate, in amounts of about 0.1 to 2%, based on the total weight of all substances, including grazing.

Colored tollers with negative polarity are obtained by combining a compound of the formula I with a compound of the formula II and those with positive polarity by combining a compound of the formula I with a compound of the formula III in the specified molar ratio range, adding a previously diazotized in the usual way dye I- lOstündiges to heating of the entire mass of a catalyst preferably in the presence to a temperature of 30 to 100 ⁰ C.

The reaction of the monomer mixtures with the dye takes place via the diazo radical following likely reaction scheme:

N ₅ Cl N ₂ ⁺ Cl CH,

Diazotize

CH, == C

COOCH,

CH ₃ CH ₃ CH ₃

H ₂ CC-CH ₂ = C CH ₂ = C

/ - \ COOCH ₃ COOCH ₃ COOCH ₂ CH ₂ N (CH ₃ J ₂

( CH ₃

—C-

COOCH ₂ CH ₂ N (CH ₃ J ₂ ;

The reactive dye is usually used based on the weight of the Monomers, about 10 to 30%. The catalyst, on the other hand, is added in an amount that each, based on the weight of the total mixture, in the case of monomers of the formulas I and 11 about 20 to 50% and in the case of monomers of the formulas I and III is about 20 to about tO%. Reaction accelerating catalysts include Compounds of the general formula

Z
CH ₂ = C

COOR

in which Z denotes a hydrogen atom or the methyl radical and R _{denotes the C n} H _{2n + 1} radical with n = 1, 2, 3 or 4, e.g. B. methacrylic acid methyl ester, ethyl ester or butyl ester, acrylonitrile or other acrylic or methacrylic acid esters.

In preparing an electrophotographic suspension developer according to the invention, the colored toner and some dispersant, e.g. B. toluene, a toner concentrate, which is then suspended in a suitable amount of a customary carrier liquid with a specific resistance of more than 10 ⁹ ohm-cm! will. Suitable carrier liquids are e.g. B. Ligroir or commercial paraffinic or isoparaffinic petroleum hydrocarbons.

The toners suspended in electrophotographic suspensions according to the invention particles have a very small particle size (0.01 to 0.1 μ), so that they can even go through the densest Run filter paper (with a pore size of 0.25 μ) through it The polymer associated with the dye or pigment is chemically linked to the dye or pigment ment particles connected, so that no precipitation or coagulation occurs as in the usual Ent

te winding as a result of the resin or oil separation is avoidable. This leaves electrophotographic suspension developers according to the invention application even over long periods of time (more than 1 year) indicates uniform dispersibility and clearly « Preserve polarity. The very small particle size of the toner particles also offers the advantage that di Ultimately obtained image copyrights have a high resolution and regardless of the type of de

Charge pattern shows no edge effect. Furthermore, this is in connection with the high particle transparency in particular in the case of electro-color photography a selective absorption and reflection of the white light, which is also true to the color laws of the three partial colors, so that the final Multicolor copy is of high quality in terms of color balance and fidelity to the original.

The following examples are intended to explain the invention in more detail.

example 1
Making a Blue Toner

A suspension of 3.5 g of finely divided tetra-4-aminocopper phthalocyanine in 40 ml of water is mixed with a mixture of 43.4 g of concentrated hydrochloric acid and 40 ml of water. The resulting hydrochloric acid solution is stirred for 30 minutes at a temperature of 0 to 5 ° C., a mixture of 8 g of ice and an aqueous solution of 1.6 g of sodium nitrite is added all at once at the same temperature and the mixture is stirred for a further 15 minutes Diazo salt solution is mixed with an emulsion of 5 g of methyl methacrylate, 10 g of lauryl methacrylate, 1 g of dimethylaminomethyl methacrylate and 1.0 g of polyoxyethylene sorbitan monostearate in 30 ml of water and is polymerized for 2 hours ^{while heating to a temperature of 60 to 70 ° C} The solution is extracted with 500 ml of toluene and the extract is concentrated to 50 ml. The residue is poured into 200 ml of methanol, causing a methanol-insoluble, highly viscous, bluish-purple plastic to precipitate, which is purified by redissolving in 50 ml of toluene and reprecipitation with methanol.

Overall, 7.5 g of a blue toner becomes more excellent Transparency and dispersibility obtained with a pronounced negative polarity.

Example 2
Making a Blue Toner

With the addition of 1 g of polyethylene glycol monostearate, an emulsion of 5 g of methyl methacrylate, 15 g of lauryl methacrylate and 3 g of hydroxylethyl methacrylate made in 30 ml of water. This emulsion is mixed with a diazo salt solution obtained according to Example 1, under Warm aaf a temperature of 60 to 70 ° C for about 2 hours, then cool and stir 500 ml of toluene extracted. 450 ml of toluene are removed from the extract, whereupon the remaining extract in 200 ml of methanol is poured. A blue-colored resin substance is deposited here. by Redissolving three times in 50 ml of toluene each time and reprecipitation with 200 ml of methanol each time and final drying is cleaned.

In total, 11.5 g of a blue toner becomes more excellent Transparency and dispersibility obtained with a pronounced positive polarity.

Example 3
Making a yellow toner ..

5 g of 2,4,6-tris- (4-amino-1-anthraquinonylamino) -1,3,5-S-triazine are dissolved in 150 g of concentrated hydrochloric acid suspended at a temperature of O '"C at once with a solution of 1.7 g Sodium nitrile in 8.5 ml of water is added and the mixture is kept at a temperature of about 0 to 2 ° C. for 30 minutes

■ 5 diazotized. The diaros salt solution obtained is treated with sulfamic acid to remove excess sodium nitrite and filtered. The filtrate obtained is mixed with an emulsion which is formed by adding 1 g of polyoxyethylene glycol ether (nonionic surface-active agent) to a solution of 10 g of lauryl methacrylate. 5 g of dimethylaminomethyl methacrylate and 1 g of p-aminostyrene in 30 ml of water have been prepared. The mixture obtained is gradually increased in temperature to 80 to about 90 ^r C ? Allowed to react for hours, after which the resulting reaction solution is extracted with 500 ml of toluene. 450 ml of toluene are evaporated from the extract; the remaining extract is mixed with 200 ml of methanol.

A yellow plastic is deposited in the process. which is purified by redissolving it three times in 50 ml of Toluo ¹ each time and precipitating it with 200 ml of methanol each time.

In total, 13.5g of a yellow toner becomes more excellent Transparency and dispersibility obtained with a pronounced negative polarity.

Example 4
Making a Yellow Toner

The diazosal / solution obtained according to Example 3 is a mixture of 10 g of methacrylic acid lauryl ester, 5 g of ethyl acrylate. 3 g of methacrylic acid glycidyl ester and 30 ml of water were added and washed through

Addition of 1 g of the surfactant mentioned in Example 3 emulsified. The emulsion obtained is allowed to react for 2 hours with a gradual increase in temperature to 80 to about 90 C, whereupon a yellow plastic is deposited and cleaned in the manner described in Example 3 will.

A total of 12 g of a good toner will be more excellent Transparency and dispersibility obtained with a pronounced positive polarity. the Color transparency of an image copy produced with a suspension developer containing this toner is very good.

Example 5
Making a Red Toner

4.7 g of a dye obtained by diazotizing 2,6-dichloro-p-phenylenediamine and coupling the Diazo compound with 3-oxynaphthoic acid-m-amino-

anilide is obtained, are suspended in 35 g concentrated 35% hydrochloric acid and ir this form is diazotized by adding 1.6 g of sodium nitrile. Be in the obtained diazonium salt solution 15 g of telauryl methacrylate. 5 g methacrylic

butyl acid ester. 2 g of vinyl benzoate and 30 ml of water are stirred in thoroughly, whereupon slowly Temperature increase to 80 to about 90C 2 hours is polymerized. The polymerization product, eir yellow plastic, is as in Example 3 Geschüderi

separated and cleaned.

A total of 12.5 g of a red toner are output excellent transparency and dispersibility with a pronounced negative polarity. Tue <

2 020

Color transparency of one containing one of these toners Image copy produced by the suspension developer is very good.

Example 6
Making a Red Toner

A mixture of 15 g of lauryl methacrylate, g of methyl methacrylate, 2.5 g of allyl methacrylate and 30 ml of water is emulsified with the addition of 1 g of sorbitan monolaurate (nonionic surface-active agent). The emulsion obtained is mixed with the diazomum salt solution prepared according to Example 5, stirred for 2 hours with a gradual increase in temperature to 80 to about 90.degree _{. C. and, after cooling, in the molded! 5}

processed in a different way to a purified red toner.

A total of 9.5 g of a red toner excellent in transparency and dispersibility becomes with a pronounced negative polarity. The color transparency of one containing this toner Image copy produced by the suspension developer is very good.

The toners produced in the manner described are used for the production of electrophotographic suspension developers by initially processed by kneading with a dispersant to a toner concentrate and then in this form in the final carrier liquid be suspended.

The individual suspension developers have the following composition.

Table I.

Colored
toner
according to
example

lot G 5 G 5 G 5 G 7.5 G 5 G 7th

Dispersants

commercial petroleum hydrocarbon 50 g

n-hexane 40 g
n-heptane 40 g

Ligroin 50 g

n-heptane 45 g

commercial petroleum hydrocarbon + commercial isoparaffinic hydrocarbon 50 g
(in a ratio of 7: 3)

Liquidity

commercial isoparaffinic

Hydrocarbon 1000 ml

Commercial ¹ petroleum hydrocarbon 10 (K) ml

commercial isoparaffinic

Hydrocarbon 1000 ml

commercial petroleum hydrocarbon +

commercial isoparaffinic

Hydrocarbon 1000 ml

(in a ratio of 4: 6)

other commercial petroleum hydrocarbons

+ commercially available isoparaffinic

Hydrocarbon 1000 ml

(in a ratio of 3: 6)

commercial hydrocarbon -

isoparaffinic 1000 ml

These six suspension developers have the properties given in Table II below:

Table II

Suspension developer gcmäti
example

2 3 4th 5 6th

polarity

negative

positive

negative

positive

positive

positive

■ ilchcn size Dispersion Stiihilitäl <0.25μ No failure at 15,000 rpm <0.25μ the same <0.25μ the same <0.25μ the same <0.25μ the same <0.25μ the same

PoUiriiiitssliibililiil

An electrophotographic recording material with zinc oxide and a styrene / methacrylic acid butyte ester / methacrylic acid glycol / acrylic acid mixed polymer (molar ratio 60: 32: 5: 3) in the light-sensitive photolayer is first applied with a -6KV corona discharge - no change in
Run of more than
I year

the same

the same

the same

the same

the same

charge, then provided with an electrostatic latent image by exposure and finally with a suspension developer of the Aft described above. In each case there is a sharp, positive one or negative color copy received. If the drawing material is recorded one after the other - under again-

high charge and development - exposed against the partial color separations of a multicolored original and then developed with the suspension developers of Examples 4, 2 and 5, one is obtained sharp multicolored image copy. s

Example 7

In a manner analogous to the previous examples, using the in the following Table III listed dyes and monomers to a number of colored toners produced. Each 1 part by weight of the respective toner is 2 to about 10 parts by weight of a commercially available petroleum hydrocarbon kneaded to a toner concentrate, which is then in each case 1000 ml of a commercially available isoparaffinic Hydrocarbon is dispersed as a carrier liquid. All suspension developers obtained have correspondingly favorable properties as the suspension developers of the previous ones Examples and the polarity given in Table III.

Table III

r «rbsiolT

2,4,6-tri-

(4-amino-

1-anthra-

quinonyl

amino) -

1,3,5,6-tri-

azin

10g

dye Lm / uset / end Vinv I connection 15g PolariUil * 5 2,6-dichloro
p-phenylene-
/ "ill ηΛtt \ 2g UlcllIllII- Methacrylic acid negative naphthoeic
acidic hexadecyl ester 5g m-amino- 4-vinyl pyridine .... chloride Methacrylic acid 25 g 3 ° 10 g methyl ester 35 g Acrylic acid vinyl positive hexyl ester 2Oe p-nitrostyrene 25 i 35 Myristic acid allyl negative ester 8g o-aminostyrene .... 10g
5g
3g Butyl myristic acid ester 5g
15g 40 Tetra
4-amino-
copper- 1-octene 8g negative phthalo- Styrene 45 cyanine Benzyl acrylamide ... 25 g Methacrylic acid 10g positive butyl ester 20 g Tridecyl vinyl ether. 50 Acrylic glycidyl ether. Methacrylic acid 8g positive hexyl ester ·. 10g Acrylonitrile Octyl acrylic acid 50 g 55 Acrylic acid 2,3-epoxypropyl- negative ester 1 ο Methacrylic acid ester 6o Acrylic acid hexyl 5g ester Methacrylic acid dibutylamino ethvlester Methacrylic acid ethyl ester

Vinyl compound

Caproic acid vinyl

ester 60 g

Diraethylacrylamide 3 g methacrylic acid ester 20 g

Palmitic acid allyl

ester 45 g

Triethanolamine acrylate .. 5 g butyl acrylate 15 g

Allyl laurate-2-methyl-

5,6-epoxy ether 10 g

Palmitic acid vinyl

ester 10 g

Methacrylic acid ester 21 g

! -Hexen 20 g

p-nitrostyrene 5 g

Methacrylic acid

heptadecyl ester .... 30 g methacrylic acid

ethyl ester 20 g

Palmitic acid vinyl

ester 35 g

p-vinylbenzoic acid 2.5 g methacrylic acid glycidylhexyl ester .. 2.5 g butyl methacrylate 15 g

Palmitic acid allyl

ester 60 g

Benzyl acrylamide ... 6 g methacrylic acid ester 18 g

Hexadecylene 40 g

p-dimethylamino

styrene 5 g

2-ethylhexyl methacrylate .. 15g Butyl methacrylate 20 g

Stearic acid vinyl

ester 50 g

Acrylic acid 15g

Methacrylic acid

2,3-epoxycster 5 g

Methacrylic acid ester 18 g

Palmitic vinyl

ester 30 g

2-chloroattiyl methacrylate ... 3.5 g Methacrylsäuredioctylamittöhexyl-

ester 3 g

Acrylic acid butyl

ester 15 g

negative

_t negative

positive

positive

positive

netiative

negative

negative

negative

Claims (3)

Patent claims: h Electrophotographic suspension developer with a toner which is a reaction product of a compound of the formula (D ίο wherein X equals the group —COOC _n H _{1n + 1} , -OCOC _n H _{2n + 1} , -OC _n H _{2n + 1} , -C _n H _{2n + 1} or, 5 —CH ₂ OC _n H _{2n + 1} with π = an integer from 6 to 7 and Y is a hydrogen atom or a methyl group, and either a compound of the formula Y, CH ₂ = C (II) 20th 25th wherein X _{1 is the} same as the group COCl —CONH, COOCH ₁ CHXl NH ₁ N (C _n H _{2n + 1} ), with Ii = an integer from 1 to 8, of the group NH, 35 40 the group —CON halogen flit R = a group 55 60 or C _n Hi _{n +} , and «= an integer from 1 to 12, of the group —COOC _n H _2n -N (C _rf H _{3rf + 1} ) ₂ , -COO-N (C _n H _{2n + 1} I ₃ H —CON (C _n H _{2n + 1} ), with η = an integer before 2 to 5 and n ' = an integer from 1 to 8 or of the group —COO — N ^ (C _n H _{2n + 1} OH) ₃ where n = 1 or 2, and Y ₁ is a hydrogen atom or a chlorine atom or a methyl group, or a compound of the formula Y, CH ₁ = C (III) wherein X is the same as the group
-COOC ₂ H ₄ OH
-OCH ₂ CH ₁ OH -COOH -CH CH ₁ -COOCH ₁ CH CH ₁ -CO-CH ₂ -CH = CH ₂ O -CH ₂ -O-CH ₁ -CH CH ₂ O -CH-CH ₁ -O-CH ₁ CH ₁ -CH Cl -COOCH ₂ CH CH ₂ CH ₂ -CH ₂ -CH CH ₂ ~ f VNO ₂ or OH and Y _{2 is} equal to a hydrogen atom or a methyl group, the molar ratio of the compound of the formula II to the compound 1 of the formula I being between 0.1: 9.9 and 3: 7 and the M ratio of the compound of the formula III to the verting of the Formula I between 1: 4 and 2: 3 is characterized by the fact that the To from a reaction product of a dye or pigment with compounds of the formulas I and II or I and IH exist. 2. Suspension developer according to claim 1, characterized in that the toner consists of a s of ^{the group} PP ^e reaction product of an amino group-containing Dye with compounds of the formulas I and II or I and III. 3. suspension developer according to claim 1, characterized in that the toner consists of a Reaction product from 10 to 30 percent by weight Dye or pigment and 90 to 70 weight ^{m! L R = a Greeting} PP ^e percent of the compounds of formulas I and II or I and III is. —CON halogen