DE2832462C3 - Electrophoretophotographic mixture or recording material - Google Patents

Description

where mean: ^3Ü

m and π = 0.1 or 2;

L ¹ to L ⁷ individually each have a hydrogen atom or an alkyl, aralkyl or aryl radical or two of L ¹ , L ² and L ³ on the one hand and / or two of L ⁴ , L ⁵ , L ⁶ and L ⁷ on the other hand, to complete atoms required of a carbocyclic ring;

R is a hydrogen atom or an alkyl

or aryl radical;

A ^{1 is} a substituted aryl radical or a

optionally substituted heterocyclic radical, their substituents from heterocyclic secondary amino radicals and / or alkoxy, amino, arylamino, dialkylamino, diarylamino, alkyl or Consist of aryl radicals and / or halogen atoms;

A ^{2 is} an optionally substituted basic imidazole; 3H-indole; thiazole; w

Benzothiazoles Naphthothiazoles Thianaphtheno-7 ', 6', 4,5-thiazole-; Oxazole-; Naphthoxazole Selenazole Benzoselenazole Naphthoselenazole-; Thiazoline-; 2-quinoline-; 4-quinolines 1-isoquinolines Benzimidazoles 2-pyridine-; 4-pyridine-; Thiazoline-; Acenaphthothiazole or one Benzoxazole nucleus

correspond to or contain such a connection. 2. Electrophoretophotographic mixture or recording material according to claim 1, characterized in that the photoelectrophoretic particles of a compound of formula 1, wherein A ^{1 is} a 2,3,6,7-tetrahydro-1H, 5H-benzo- [ij] quinolizine nucleus or a optionally substituted phenyl radical whose substituents consist of alkoxy, dialkylamino, morpholino, di-p-tolylamine or pyrrolidomine radicals, correspond to or contain such a compound.

The invention relates to an electrophoretophotographic mixture or recording material which Contains photoelectrophoretic particles.

It is well known to produce images by means of an electrophoretophotographic imaging process, in which a layer of a suspension of photoelectrophoretic particles is imagewise exposed and in which an electric field is applied to the suspension. Such imaging processes are for example from US-PS 58,939, 29 40 847, 3100 426, 3140 175, 3143 508. 84 565, 33 84 488, 36 15 558, 33 84 566 and 33 83 993 as well as from DE-AS 14 97 243, 16 22 380 and'i6 68 992 and also the DE-OS 15 22 727, 19 47 333 and 22 63 494 known. Except for those in these publications The conventional electrophoretophotographic imaging process described is another type of one Elektnjphoretophotographisftien imaging process, in which an image reversal takes place, from US-PS 39 76 485 become known. This in this patent ^ The procedure described in this document is also known as the PIER procedure known.

In the known electrophoretophotographic imaging processes, typically a Layer of electrostatic charge-bearing photoelectiophoric particles between two im

Spaced electrodes, one of which may be transparent, housed To To be able to produce an image, the photoelectrophoretic ones arranged between the electrodes are used Particles exposed to the action of an electric field and with light such Wavelength exposed to which the particles are sensitive. As a result, the migrate photoelectrophoretic particles to the surface of one or the other of the two at a distance mutually arranged electrodes, with the generation of images on the electrode surfaces. In typically a negative image is created on the opposite electrode. An image resolution occurs as a result of the various known electrophoretophotographic imaging processes a change in the charge polarity of either the exposed particles (in the case of the usual known electrophoretophotographic imaging processes) or the unexposed particles (im Case of the electrophoretophotographic imaging method known from US Pat. No. 3,976,485 Type), so that the image generated on an electrode surface ideally consists of particles of one charge polarity, either more negative or positive Polarity is built up and the image on the surface of the electrode of opposite charge polarity im Ideally, the trap is built up from particles which have an opposite charge polarity, i.e. H. one positive or negative charge polarity.

In any case, be indifferent to the type of electrophoretic process used photoelectrophoretic particles are required to carry out the process. To get an easily visible picture It is essential that these photoelectrophoretic particles are colored and electrically photosensitive are.

There has therefore been no lack of attempts to find photoelectrophoretic particles which have both a have advantageous electrical photosensitivity as well as good coloring properties.

It is known to carry out the most varied types of photoelectrophoretic particles of electrophoretophotographic imaging processes. Such particles are for example from US-PS 27 58 939, 29 40 847, 33 84 488 and 36 15 558 known.

In large part they have been used to date for performing electrophoretophotographic Image forming process, electrically photosensitive and / or photoconductive particles from known Classes of photoconductive substances selected which are used for the production of conventional photoconductive recording materials, d. H. Photoconductive plates, drums or belts can be used, which in turn are used for Performing electrophotographic office copying processes are useful. From US-PS 27 58 939 and 29 40 847 it is known, for example, that electrically photosensitive particles for the implementation of electrophoretophotographic imaging processes from bekarη- .. '. '' let off photoconductive Materials can be selected. It is also known, for example, that the phthalocyanine pigments, that in US Pat. No. 3,615,558 as being useful in performing electrophoretophotographic imaging processes specified have photoconductive properties. The use of phthalocyanine pigments in the context of electrophoretophotographic Imaging method is also known from DE-AS 14 97 243 In the case of the DE-OS 22717 known photoelectrophoretic particles are so-called. Triphenodioxazines, in the from DE-AS 16 22 380 known particles around pyrenes and those known from DE-AS 16 68 992 Particles around special azo metal complex salts. the The use of dioxazine pigments is also known from DE-OS 22 63 494. From DE-OS 19 47 333 is ίο It is also known as photoelectrophoretic particles to use brominated azo pigments.

The object of the invention is an electrophoretophotographic mixture or recording material with further improved properties, in particular advantageous dyeing properties as well as advantageous electrical properties.

It has been found that the problem posed can be achieved with certain pigments which are compounds with an isoxazolin-5-one nucleus.
The invention thus provides an electrophoretophotographic mixture or recording material as characterized in the claims.

In the formula I given in claim 1, A ^{1 is}

thus for a substituted aryl radical, for example the phenyl, naphthyl or anthryl series or an optionally substituted heterocyclic nucleus.

z. B. a

Thiophene; Benzo [b] thiophene-;
Naphtho [2,3] thiophene-; Furan; lsobenzofuran;
Chromene; Pyran; Xanthene; Pyrrole; 2H-pyrrole-; Pyrazole-; Indolizine indoline; Indole; 3H-indole-;
Indazole-; carbazole-; Pyrimidines isothiazole;
Isoxazole-; Furazan; Chroman; Isochroman;
1,2,3,4-tetrahydroquinoline-;
4H-pyrrolo [3,2, l-ij] quinoline-;
1,2-dihydro-4H-pyrrolo [3,2, l-ij] quinoline-;

l ^ ijJhi

1 H, 5H-benzo [ij] quinolizine-;
2,3-Dihydro-1H, 5H-benzo [ij] quinolizine-:
2,3-dihydro-1 H, 5 H -benzo [ij] quinolizine-;

2,3,6,7-tetrahydro-1H, 5H-benzofij] quinolizine-;
10, ll-Dihydro-9H-benzo [a] xanthen-8-yl- or
6,7-dihydro-5H-benzo- [b] pyran-7-ylkem,
where the nuclei can be substituted, for example, by a heterocyclic secondary amino and / or an alkoxy, amino, arylaniino, dialkylamino, diarylamino, alkyl and / or aryl radical and / or halogen atoms.

In the given formula II, the ^{core represented by A 2} consists of:

a) an imidazole nucleus, e.g. B. an imidazole or 4-phenylimidazole nucleus;

b) a 3H indole core, e.g. B. a 3H-indole; 3,3-dimethyl-3H-! Ndol- or a 3,3,5-trimethyl-3H-indole nucleus;

c) a thiazole nucleus, e.g. B.

a thiazole; 4-methyithiazole;
4-phenylthiazole-; 5-methylthiazole-;
bo 5-phenylthiazole-; 4,5-dimethylthiazole-;

4,5-diphenylthiazole or a
4- (2-thienyl) thiazole nucleus;

d) a benzothiazole nucleus, e.g. B.
a benzothiazole

hi 4-chlorobenzothiazole-;

5-chlorobenzothiazole-;
6-chlorobenzothiazole-;
7-chlorobenzothiazole-;

4-methylbenzothiazole-; 5-methylbenzothiazole-; 6-methylbenzothiazoI-; 5-bromobenzothiazole-; 6-bromobenzothiazole-; 4-phenylbenzothiazole-; 5-phen ibenzothiazole-; 4-methoxybenzothiazole-; 5-methoxybenzothiazole-; 6-methoxybenzothiazole-; 5-iodobenzothiazole-; 6-iodobenzothiazoI-; 4-ethoxybenzothiazole-;

5-ethoxybenzothiazole-; Tetrahydrobenzothiazole-; 5,6-dimethoxybenzothiazole:

5,6-dioxymethylene benzothiazole; 5-hydroxybenzothiazole-; or 6-hydroxybenzothiazole nucleus;

e) a naphthothiazole nucleus, e.g. B. a naphtho [1,2-d] thiazole-; Naphtho [2, l-d] thiazole-; Naphtho [2,3-d] thiazole-; 5-methoxynaphtho [2, l-d] thiazole 5-ethoxynaphtho [2, l-d] thiazole-; 8-methoxynaphtho [1,2-d] thiazole or a 7-methoxynaphtho [1,2-d] thiazole nucleus;

f) a thianaphtheno-7 ', 6', 4,5-thiazole nucleus, e.g. B. a 4'-methoxythianaphtheno-7 ', 6', 4,5-thiazole nucleus;

g) an oxazole nucleus, e.g. R.

a 4-methyloxazole; 5-methyloxazole-; 4-phenyloxazole; 4,5-diphenyloxazole;

4-Ethyloxazole-; 4,5-Dimethyloxazole- or

a 5-phenyloxazole nucleus; h) a naphthoxazole nucleus, e.g. B.

a naphtho [1,2] oxazole or a

Naphtho [2,1] oxazole nucleus; i) a selenazole nucleus, e.g. B. a 4-methylselene

azole or a 4-phenylselenazole nucleus; j) a benzoselenazole nucleus, e.g. B.

a benzoselenazole 5-chlorobenzoselenazole-; 5-methoxybenzoselenazole-; 5-Hydroxybzoselenazol- or a

Tetrahydrobenzoselenazole nucleus; k) a naphthoselenazole nucleus, ζ. Β.

a naphtho [l, 2-d] or a

Naphtho [2,1-d] selenazole nucleus; I) a thiazoline nucleus, e.g. B. a thiazoline or

a 4-methylthiazoline nucleus; m) a 2-quinoline nucleus, e.g. B.

a quinoline; 3-methyichinoiin-; S-Methylquinoline - ^ - MethylchinoIine S-methylquinolinee-chloroquinoline-; S-chloroquinolineö-methoxyquinoline-; 6-ethoxyquinoline-; 6-hydroxyquinoline-;

or an 8-hydroxyquinoline nucleus; n) a 4-quinoline nucleus, e.g. B. a quinoline; 6-methoxyquinoline-; 7-methylquinoline or a

8-methylquinoline nucleus; o) a 1-isoquinoline nucleus, e.g. an isoquinoline

or a 3,4-dihydroisoquinoline nucleus; p) a benzimidazole nucleus, e.g. B. a 13-diethyl

benzimidazole or a l-ethyl-3-phenylbenz-

imidazole nucleus;
q) a 2-pyridine nucleus. z. B. a pyridine or 5-methylpyridine nucleus;

r) a 4-pyridine nucleus;

s) a thiazoline nucleus;

t) an acenaphthothiazole nucleus or

u) a benzoxazole nucleus.

Alkyl radicals here are preferably those with 1 to understand up to 20 carbon atoms, z. B. methyl, ethyl, propyl, isopropyl, butyl, heptyl, dodecyl or Octadecyl residues. The aryl radicals mentioned here have

ίο preferably have 6 to 20 carbon atoms and exist preferably from residues of the phenyl, naphthyl or anthryl series. These aryl radicals can optionally be substituted by alkyl and / or aryl radicals. This means that the aryl radicals, for example, from such

Residues such as ToIyI-, Athylphenyl- or Biphenylresten can exist. Aralkyl radicals are to be understood as meaning alkyl radicals substituted by aryl radicals, for example benzyl or phenethyl radicals.
Carbocyclic radicals are to be understood here as meaning saturated carbocyclic rings which can optionally be substituted by alkyl, aryl or aralkyl substituents of the structure indicated. This means that the carbocyclic radicals, for example, from cyclopropyl, cyclophenyl, cyclohexyl or

> ^r > 5,5-dimethylcyclohexyl radicals can exist. The alkoxy radicals mentioned here are preferably alkyloxy radicals in which the alkylresl has the meaning given. Typical alkoxy radicals are, for example, methoxy, ethoxy, isopropoxy and

so butoxy residues.

When used in the context of an electrophoretophotographic imaging process, the photoelectrophoretic particles between at least two spaced apart

r> electrodes housed.

The particles are preferably contained in an electrically insulating carrier, e.g. B. one electrically insulating liquid or an electrically insulating, liquefiable matrix, e.g. B. a thixotropic or material softenable by the action of heat and / or solvents that is between the electrodes is brought. The particles accommodated between the electrodes then become the Exposed to the action of an electric field and exposed imagewise, with radiation from the are sensitive to them. As a result, their charge polarity is changed so that they become the one or others migrate on the electrode surface, forming an image on at least one of the Electrode surfaces, which is a positive or negative image of the original.

In the drawing is a device for schematically Carrying out such a mapping process in which the photoelectrophoretic particles can be used.

According to a particularly advantageous embodiment of the invention, the particles correspond to one of the formulas I or II, in which:
A ^{1 is} a 23,6,7-tetrahydro-1H.SH-benzoTjjJchinoIizinkern or an optionally substituted phenyl radical, which is optionally replaced by one or more

Alkoxy, dialkylamino, morpholino, di-p-tolylamino and / or pyrrolidino radicals can be substituted;

A ^{2 is} an optionally substituted heterocyclic

t> 5 see core, namely a thiazole; Thiazoline-; Benzothiazoles Naphthothiazoles Benzoxazole-; Benzoselenazole 2-quinoline-; 4-quinoline or a 3H-indole nucleus;

L ¹ to L ⁷ , m and η have the meanings already given.

In general, particles with a compound of one of the formulas I and II have a maximum absorption wavelength λ max of 420 to 750 nm.

Typical compounds which can be used according to the invention are listed in the following table.

The compounds of the formulas I and II can be prepared, for example, by processes as described in Journal »Journ. of American Chemical Society ", 35, page 959 (1913) and in the Journal of American Chemical Society ", 73, pages 5326-5363 (1951) and U.S. Patents 2,165,339 and 29 56 881 to be discribed.

Table I.

No.

Structural formula

hue

N
C ₂ H ₅

N
C ₂ H ₅

CH-CH = CH-CH = I.

Purple

CH-CH

C ₂ H ₅

yellow

[IV = CH-CH = CH-CH = / I ^ 1NK V / N

purple

HP ί \ = CH - CW = / I

C ₂ H ₅

purple

CH-CH = CH-CH = CH-Ch = / O blue green

continuation

No structural formula

hue

r _s l. ₂

-CH = CH-CH = I

C ₂ H ₅

purple

CH-CH = CH-CH = TO

CH ₃ CH ₃

V ^s

CH-CH = CH

C ₂ H ₅ purple

blue

O green

10

S / ^ O

\ = CH-CH = CH-CH = <; I.

! T

CH ₂ purple

11th

VCH-

C ₂ H ₅

orange

Continuation

12th

Structural formula hue

CH ₃

V ^s

CH-CH = CH-CH

C ₂ H ₅

orange

purple

V ^s

= CH-CH = <

C ₂ H ₅ orange

CH-CH =

C ₂ H

2Π ₅

orange

'VS \

C - CH = CH - CH

^ N / I

i

C ₂ H ₅

O
O

- / N

purple

C-CH = CH-CH CH ₃

C ₂ H,

purple

13th

Forfsetzune 14

Structural formula hue

V ^s

CH ₃

V = CH-

> = CH —CH = CH-

C ₂ H ₅

CH-CH

C ₂ H,

orange

purple

blue

orange

pink

purple

15th

Continued 16

Structural formula hue

C ₂ H ₅ -N

CH - CH = CH-CH

blue

CH-CH = CH-CH = Ch-CH

green

CH-CH = CH-CH

purple

CH ₃ -N CH-CH = CH-CH = CH

C ₂ H ₅ -N

CH- CH

orange

17th

continuation

18th

No.

Structural formula

hue

29 30

32

orange

purple

pink

pink

orange

Reddish brown

continuation

No.

Structural formula

hue

35

36

37

38

39

H ₃ C

H ₃ C

orange

purple

blue

orange

orange

Those for performing v> n electrophoretophotographic Figure ve:. \ Ih; c.i certain photoelectrophoretic Particles advantageously have an average particle size of 0.01 Microns to 20 microns, especially from 0.01 to 5 microns.

The photoelectrophoretic particles can optionally contain various non-light sensitive components have e.g. B. electrically insulating polymers, charge control agents, a wide variety of organic and inorganic fillers, as well as various other additional dyes or Pigments, for changing or further improving the coloring and physical properties of the particles. Furthermore, the photoelectroohoretic Particles of other light-sensitive substances

included, ζ. B. the most diverse sensitizing dyes and / or chemical sensitizers, about their response characteristics to the wavelengths of light to which they are exposed are sensitive to modify or increase.

The photoelectrophoretic particles described can be in a simple manner in the form of a dry powder placed between electrodes and then a typical electrophoretophotographic Imaging processes are subjected, for example a process such as that disclosed in US Pat 27 58 939 is known.

Most typically, the photoelectrophoretic particles are in an electrically insulating Carrier dispersed, e.g. B. an electrically insulating liquid or an electrically insulating, liquefiable matrix, e.g. B. a softenable by the action of heat and / or solvents Polymer or a thixotropic polymer. Are dispersions of the photoelectrophoretic particles in If an electrically insulating carrier is used, it has proven to be expedient, 0.05 parts by weight to 2.0 Parts by weight of particles for every 10 parts by weight of electrical to use insulating support.

The customary known carriers can be used to prepare the carrier dispersions, ie electrically insulating liquids, e.g. B. decane, paraffin and kerosene fractions. It is also possible to use, for example, a wide variety of isoparaffinic liquid hydrocarbons, for example carbon jo hydrogen fractions with a boiling range from 145 to 186 ° C. and a wide variety of halogenated hydrocarbons, e.g. B. carbon tetrachloride and trichloromonofluoromethane and various alkylated aromatic liquid hydrocarbons, κ ζ. B. alkylated benzenes, e.g. B. xylenes and other alkylated aromatic hydrocarbons, as they are known for example from US Pat. No. 2,899,335. Typically, regardless of whether the carrier is solid or liquid at normal room temperature, ie about 22 ° C., the electrically insulating carrier has a resistance of over 10 ⁹ ohm / cm, preferably of over about 10 ¹² ohm / cm. If the photoelectrophoretic particles are used in a carrier, for example in one of the above-mentioned electrically insulating liquids, a wide variety of customary known additives can be incorporated into it, for example a wide variety of charge control agents, in order to ensure the uniformity of the charge polarity of the particles present in the liquid suspension to enhance. Typically, such charge control agents are polymeric compounds which can be mixed into the liquid carrier of the suspension. It has been found that the addition of charge control agents, in addition to improving the uniformity of charge polarity, often leads to the production of more stable suspensions, ie suspensions in which the dispersed photoelectrophoretic particles settle considerably less quickly than in the case of suspensions without the addition of Charge control agents.

In addition to the charge control agents mentioned, a wide variety of polymeric binders can be used can be added. These binders can be natural, semi-synthetic or synthetic in origin and be dispersed or dissolved in the electrically insulating carrier. Let with her help the produced particle images are fixed on the electrodes.

In the drawing is one for performing an electrophoretophotographic imaging process suitable device shown in the scheme

The device has a transparent electrode 1, which is driven by two drive rollers 10 in the by the Direction indicated by arrows can be moved. The electrode 1 can consist of a layer of an optical consist of transparent material, e.g. B. glass or an electrically insulating, transparent polymer substrate, e.g. B. of polyethylene terephthalate, the Layer support with a thin, optically transparent, conductive layer, e.g. B. of tin oxide, indium oxide or Nickel can be coated. If necessary, depending on the type of procedure used in the individual case, can the surface of the electrode 1 is a "dark charge exchange material" have e.g. B. in the form of a solid solution of 2,4,7-trinitro-9-fluorenone in an electric insulating polymer. Reference is made in this context to US Pat. No. 3,976,485.

At a distance from the electrode 1 and in pressure contact with the same is the second electrode 5, the in the present case is designed as a roller electrode or guide electrode and the counter electrode represents the electrode 1 Typically, the electrode 5 has a thin electrically insulating Layer 6 on. The electrode 5 is connected to one side of the power source 15 via the switch 7. the opposite side of the power source 15 is connected to the electrode 1 so that when an exposure takes place, the switch 7 is closed and the particles 4 exposed to the action of an electric field will. The photoelectrophoretic particles 4 are typically located in an electrically insulating one Carrier pre-dispersed.

The photoelectrophoretic particles 4 can thereby be arranged between the electrodes 1 and 5 will cause the particles to be sprayed onto either or both of the surfaces of the electrodes 1 and 5 before the procedure is carried out or by the fact that they are carried out during the implementation of the electrophoretophotographic imaging process can be injected between electrodes 1 and 5.

As can be seen from the drawing, the photoelectrophoretic particles 4 are exposed by an exposure system from a light source 8, the original to be reproduced 11, z. B. a photographic Slide, a lens system 12 and optionally radiation filters 13, for example Color filters, whereby the photoelectrophoretic particles 4 according to the template 11 Bildgerechi to be exposed.

Although the device shown in the drawing is an electrode 1 which is responsible for the radiation of the Light source 8 is permeable but it is also possible to place the photoelectrophoretic particles 4 in the Spall 21 to irradiate between the electrodes 1 and 5 without one of the electrodes 1 or 5 permeable or needs to be transparent In such a device, the light source 8 and the lens system 14 be arranged so that the particles 4 in the gap 21 between the electrodes 1 and 5 are exposed.

In the device shown in the drawing isi the electrode 5 is formed into a roller electrode which has a conductive core 14 to which the Power source 15 is connected. This core is in turn covered with a layer of an insulating Material 6, for example a baryta paper

coated. The insulating material 6 has the task of preventing the photoelectrophoretic Particles 4 are subject to a radiation-induced change in charge on contact with the electrode 5. At least the layer 6 should reduce this tendency of the particles. As a result, the electrode 5 can also be referred to as the so-called "blocking electrode".

Although the electrode 5 is shown in the present case in the form of a roller electrode and the Electrode I in the form of a flat plate electrode, but both of these electrodes can also be different have conventional shapes, for example the shape of ribbon-shaped electrodes, rotating roller electrodes or plate electrodes.

In general, when performing a typical electrophoretophotographic imaging process, there are in which the particles 4 are dispersed in an electrically insulating liquid carrier, the electrodes 1 and 5 are in pressure contact with one another or are very close to one another, i. e. H. your The distance from each other is typically less than 50 microns. On the other hand, the photoelectrophoretic ones Particles 4 easily disperse in an air gap between electrodes 1 and 5 or in a support such as a layer of heat softenable or otherwise liquefiable material in the form of a layer on the electrode 1 and / or 5 housed, these electrodes can be more than 50 apart during the imaging process Have microns of each other.

The strength of the electric field applied to electrodes 1 and 5 while the Procedure applied can be very different. It has been shown, however, that in general a optimum image density and resolution can be obtained when the field strength is as large as is possible, d. H. has as high a value as possible without an electrical breakdown of the carrier in the gap between the electrodes takes place. If, for example, an electrically insulating carrier is used If a liquid is used, for example an isoparaffin-hydrocarbon-based carrier, then, if used a device as shown in the drawing, which is connected to the electrodes I and 5 in typical Wise applied voltage will be 100 volts to 4 kilovolts or more.

In order to achieve particularly advantageous results, the field action and the Exposure at the same time. By suitable selection of the various process parameters, for example the Field strength, the intensity of the activating radiation, by adding suitable light-sensitive additives the photoelectrophoretic particles or by using such additives with the particles or however, by adding a persistent photoconductive material, it is also possible to change the time sequence of To change exposure and field exposure in such a way that exposure and field exposure are sequential can be done instead of at the same time.

The photoelectrophoretic particles 4 accommodated between the electrodes 1 and 5 have a electrostatic charge polarity either as a result of a triboelectric action of the particles or as a result of an action by the carrier in which the particles are dispersed on the latter, e.g. B. the electric insulating liquid, as in the case of conventional liquid electrographic suspension developers made from toner particles, which take on a charge when dispersed in an electrically insulating carrier liquid will.

When performing a typical imaging process, the particles become when an electrical Field to electrodes 1 and 5 in the dark either attracted by electrode 1 or 5, depending on which of these electrodes has a polarity that the

ι is opposite to the original charge polarity of the particles. Presumably, the exposure takes place Particles 4 a neutralization or reversal of the charge polarity, either in the case of exposed or in the case of the unexposed particles. In the case of a typical electrophoretophotographic The mapping process in which the electrode ί has a conductive surface are subject to the exposed particles 4 when they come into electrical contact with the conductive surface of a change (usually a reversal) of their original charge polarity as a result of the combined action of electric field and activating radiation.

In the case of the so-called PIER procedure in which the Surface of the electrode 1 has a layer of a dark charge exchange material (see. US-PS 39 76 485) alternatively a reversal of the charge polarity of the unexposed particles is obtained while the exposed particles retain their original charge polarity when they are in electrical Come into contact with the dark charge exchange material of electrode 1. In any case, it can be The effect of an electric field and activating radiation on the particles 4 results in an effective image resolution so that an image is produced which corresponds to the original. Typically at Using a device of the type shown in the drawing, a visible image on the surface of the electrode 1 and a complementary image on the surface of the electrode 5.

Following the action of the electric field and following the exposure, the Images generated on the surface of the electrodes 1 and 5 temporarily or permanently on these electrodes fixed or transferred to image receiving materials. The fixation of the particle images can be achieve by conventional methods, for example by applying a resinous top layer to the Surface of the substrate carrying the image. For example, if the particles 4 are in a liquid carrier dispersed between the electrodes 1 and 5, so can the image or can be the images that appear on the Surfaces of the electrodes 1 and / or 5 are generated by fixing the carrier liquid a polymeric binder is added. Many such binders, their use in liquid electrophotographic Known to suspension developers, are known to change their charge polarity, when mixed with a carrier liquid, so do the binder particles themselves Surface of one or the other of the electrodes migrate. Alternatively it is possible to have a layer a resinous binder (such as can be used in the carrier liquid, for example) on the To generate surface of the electrodes 1 and / or 5 after the liquid carrier has been evaporated.

The described photoelectrophoretic particles with or from compounds of the formulas I and II

can be used to produce monochrome images or after mixing with other photoelectrophoretic images Use particles of a different color to create polychrome images.

The photoelectrophoretic particles described can also be used in the production of Use monochrome images as sensitizers for other photoelectrophoretic particles. If the particles are mixed with other photoelectrophoretic particles, the particles used according to the invention selectively as sensitizers and / or as photoelectrophoretic ones Particles work.

Many of the photoelectrophoretic particles according to the invention have particularly advantageous color tones on, which is why they are used in a particularly advantageous manner in the context of polychrome imaging processes let, in which a mixture of two or more differently colored photoelectrophoretic Particle is used. If such a mixture of different colored particles is produced, for example in an electrically insulating carrier liquid, this mixture of particles can have a black in color. Preferably, cyan, magenta and yellow particles are used for the Carrying out polychrome imaging processes selected in such a way that their spectral Response curves do not noticeably overlap, making color separation and manufacturing more subtractive Multi-color images is made possible.

The following examples are intended to illustrate the invention in more detail. They describe the use of Compounds of formulas I and II as part of an electrophoretophotographic imaging process.

Examples Ibis39
Device used

An apparatus as shown in the drawing was used to carry out the process. A film substrate with a conductive layer composed of a heat-resistant component (SiO) and a metal component (Cr) of the formula CrSiO with an optical density of 0.1 was used as the electrode 1. The electrode 1 was in pressure contact with an aluminum roller 14, 10 cm in diameter, coated with a dielectric paper coated with a poly (vinyl butyral) resin. The aluminum roller 14 served as electrode 5. The electrode 1 was located on two rubber drive rollers 10 with a diameter of 2.8 cm. The two drive waves were located at such a distance from one another that a 2.5 cm opening was created, symmetrical to the axis of the aluminum roller 10 , whereby the exposure of the photoelectrophoretic particles 4 was made possible. The slide template 11 to be reproduced was stuck to the back of the electrode 1

The slide to be reproduced consisted of adjacent strips of Wratten filters, namely a transparent filter, a red filter, a green filter and a blue filter. The light source used consisted of a projector with a 1000 watt xenon lamp. The light was modulated by a step wedge with 11 density steps of a neutral density of 0.3. The dwell time in the exposure zone was 10 milliseconds. The logarithm of the light intensity (Log I) was as follows:

filter

Log I.
Erg / cm ² / sec.

Transparent
Red
green
blue

5.34
4.18
4.17
4.15

The voltage applied to electrodes 1 and 5 was about 2 KV. The electrode 1 had a negative polarity in the case where the photoelectrophoretic particles 4 had a positive electrostatic charge. The electrode 1 was the positive polarity electrode in the cases where the photoelectrophoretic particles 4 were negatively charged. The advancing speed of the electrode 1 was about 25 cm per second. In the case of these examples, an image was formed on the surfaces of the electrodes 1 and 5 with simultaneous exposure and the application of an electric field to the photoelectrophoretic particles 4 which were in a liquid carrier. The particle dispersion was accommodated in the gap 21 between the electrodes 1 and 5. In the case in which the particles 4 exhibited sufficient electrical sensitivity, a negative image of the original 11 on the electrode 5 and a complementary image on the electrode 1 were produced.

Preparation of the imaging dispersions

Starting from the compounds listed in Table I, various dispersions were prepared.

j5 A was used to prepare the dispersions Starting solution from the components indicated below. This starting solution was made by simply combining the components listed below.

Mixture of isoparaffin hydrocarbons

with a boiling point range of

145 to 186 ° C

Mixture of alkylated aromatic

Hydrocarbons with a
Boiling point range from 157 to 177 ° C

Polyvinyltoluene-styrene copolymer

Mixed polymer

Vinyl toluene, lauryl methacrylate,

Lithium methacrylate and methacrylic acid
in the ratio 56: 40: 3.6: 0.4 (PVT)

2.2 g

1.3 g

1.4 g

0.1g

in a closed container were each 5 g the starting solution described with 0.045 g of a compound from Table I and 12 g of balls stainless steel combined. The mixture was then agitated on a shaker for 3 hours shaken

Each of the 39 compounds listed in Table I was tested.

to It was found that each of the compounds tested had advantageous properties photoelectrophoretic, which revealed himself to the fact that in each case a negative image of the original on one of the electrodes and a complementary image was formed on the other electrode. The image quality was determined visually. In all cases, advantageous images with advantageous minimum and maximum densities, good sensitivity and color saturation were obtained.

1 sheet of drawings

Claims (1)

Patent claims: l.Elektrophoretophotographic mixture or records that the photoelectrophoretic Recording material, the photoelectrophoretic particle of a compound one of the general contains particles, characterized by 5 formulas: or Π. A ² = CL ⁴ - CL ⁵ = Φ CL ⁶ - CL