DE1282449B - Photosensitive layers - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY GERMAN 40BTWW PATENT OFFICE Int. Cl .:

G03c

EDITORIAL

German class: 57 b -1/72

Number: 1282449

File number: P 12 82 449.6-51 (H 53745)

Filing date: September 10, 1964

Open date: November 7, 1968

The invention relates to light-sensitive layers containing a leuco compound of the formulas

Rx

(D Photosensitive layers

(H)

(NI)

where R is H, (Ci-C>) - alkyl or aryl, Ri is the same H, alkyl, aryl or

Applicant:

Horizons Incorporated, Cleveland, Ohio (V. St. A.)

Representative:

Dr. W. Schalk, Dipl.-Ing. P. Wirth, Dipl.-Ing. G. M. Dannenberg and Dr. V. Schmied-Kowarzik, patent attorneys, 6000 Frankfurt, Große Eschenheimer Str.

Named inventor: Robert H. Sprague, Chagrin Falls, Ohio; John A. Stewart, Parma, Ohio; James M. Lewis, Cleveland, Ohio (V. St. A.)

Claimed priority: V. St. v. America September 17, 1963 (309407)

The subject of the invention is based on a photosensitive layer with a leuco compound 30 of the formulas

and Z is O, S, Se or NH, a colorless, nitrogen-containing heterocyclic compound as Activator and optionally a binder.

It is known to copy out photosensitive layers with at least one activator and one to use oxidizable leuco base. A triphenylmethane dye has also been proposed to use as a leuco base and the photosensitivity of the photographic recording material, especially to improve against ultraviolet light by adding certain aldehydes, esters and ketones.

Disadvantages of the already known or proposed photographic recording materials of the kind mentioned is that this still does not have a satisfactory sensitivity to visible and ultraviolet light.

The object of the invention is to provide photosensitive layers which can be copied out directly and which have an improved Have sensitivity to visible and ultraviolet light.

\ _R (HD

10 «630/992

where R is H, (Ci-C ₂ ) -alkyl or aryl, Ri are the preferred leuco compounds of the others

equal to H, alkyl, aryl or class are preferably substituted in the 3,6-position.

J ^ The following Leukover-

/ bindings:

■ N 5

\ £ 3,6-bis (diethylamino) -9- (p-dimethylammo-

phenyl) -xanthene,

and Z is O, S, Se or NH, a colorless, 3,6-bis- (diethylamino) -9- (p-diethylamino-

nitrogen-containing heterocyclic compound as phenyl) -xanthene or

Activator and optionally a binder from io 3,6-bis (dimethylamino) -9- (p-dimethylamino-

and is characterized in that it is phenyl) thioxanthene as an activator.
a triazole or a heterocyclic ketimide with

Contains 5 or 6 ring atoms. According to a further embodiment of the invention In the photosensitive according to the invention contains the photosensitive layer as a leuco

Layers as activators present colorless 15 compound 3,6-bis- (dimethylamino) -9- (p-dimethyl-

Triazoles or heterocyclic ketimides with 5 or aminophenyl) -xanthene.

6 ring atoms can exist in two tautomeric forms The production of photographic records, namely as voltage materials with the inventive light

/ \ sensitive layer can be known in per se

* / \ 20 way, preferably one will be

hetero- CH ₂ thin layer with the light-sensitive compounds

cyclic | fertilize applied to an inert substrate,

Ring C = NH where a support made of a film-forming

\ / - Plastic, which may be transparent, very much

\ _v / 25 works well.

or as a binder can be any for the production of

y \ photographic recording materials usual

/ \ Binders are used. According to an

hetero- CH design of the invention includes the photosensitive

cyclic || 3rd layer as a binder cellulose or a cellulose

Ring _% C-NH ₂ derivative.

In order to investigate the photosensitivity of photosensitive layers according to the invention, The following procedure was used: It seems that the effective form of the activators was a mixture of 2 ecm acetone and one Structure with the imide group, however, 10% polystyrene solution is made in benzene, the mechanism of action not yet known. Here 3,6-bis (dimethylamino) -9- (p-dim-

As activators, the following compounds are thylaminophenyl) -xanthene in the same amount as particularly preferred: the activator used, as shown in Table I

40 is performed, solved. The obtained coating liquid was coated on a support made of a

t? ς rhi tv. τ * 1 The exposure of the photosensitive

ß. z ^ nioroenzinazoi _{4J Hchen Materials} . ^ _11n J ₆ either with a reflector-

According to one embodiment of the invention, the photolamp is made by a step wedge,

the light-sensitive layer as an activator Benz- for 5 minutes with the 30 cm from the light-

triazole or isoxazolonimide. removed sensitive recording material

In the photosensitive lamp according to the invention or in a sensitometer using

Layer are also color-forming leuco compounds 50 of a suitable daylight filter,

contain, namely either leukotriaryl methane.

dyes or leuco compounds that differ from a stable, practically usable image

Leukoxanthenen, Leukothioxanthenen and Leuko- to produce, two known processes

acridines and turns from leukotriaryl methane. In one process the was exposed

dyes due to the presence of one or more recording material two or more times

differentiate between several bridge heteroatoms. a mixture of 1 part acetone and 4 parts

Preferred petroleum ethers are rinsed as leukotriarylmethane dyes. The other method

wise the following or similar compounds, the exposed recording material was 4Mi-

turns: take a long groove in a convection oven at 125 ° C

60 heated.

Leuco crystal violet, after fixation became photographic

LeukoopalbUu, recording material for another 4 minutes

Leuco malachite green, total with a photo lamp without darkening

LeukorosaöiUa or exposed. The evaluation of the exposed, light-

Leuko-p-rosanilln, 65 sensitive recording materials was

P »p'.p" -TrtoetiiyHeukoopalblau, made by that the density and the number

p.p ^ -Trichlor-leukoopalblau, according to the steps visible in the resulting picture

p.p'-bi-tetraethyl-diaminodiphenylmethane. the fixation was read.

5 6

The results obtained with the exposures are shown in the table below.

No. of levels Activators weight Fixäerungsart Gross density Density of
Layer support + veil Number of sight
available levels 18th A. 50 solvent 1.56 0.19 18th 11 B. 50 solvent 0.51 0.15 ■ 11 18th C. 50 solvent 1.11 0.14 18th 17th D. 100 warmth 1.24 0.30 17th 9 100 solvent 0.41 0.12 9 12th E. 100 solvent 0.41 0.14 12th

Similar results were also obtained using leuco crystal violet as the leuco compound and obtained from 5-chlorobenzotriazole as an activator. If the 5-chlorobenzotriazole is replaced by 3-naphthylisooxazolonimide, thus a blue image of comparable density is obtained.

The photochemical mechanism in the exposure of the photosensitive layer is still not fully clarified. There is reason to believe that the image obtained is composed of a dye which is an oxidation product of the leuco base used. The active component of the photosensitive The layer appears to be a small amount of an oxidation product of the leuco base, that formed with the oxygen in the atmosphere.

The invention achieves that in the case of a photographic recording material which is to be copied out directly improved photosensitivity is obtained and stable, practicable Images are to be produced.

Claims (4)

Patent claims: 1. Photosensitive layer with a leuco compound of the formulas wherein R is H, (Ci-C ₂ ) -alkyl or aryl, Ri is H, alkyl, aryl or / ^R and Z is O, S, Se or NH, a colorless, nitrogen-containing heterocyclic compound as an activator and optionally a binder, characterized that they are a triazole or a heterocyclic ketimide with 5 or 6 ring atoms as an activator contains. 2. Layer according to claim 1, characterized in that it is used as an activator or benzotriazole Contains isooxazolonimide. 3. Layer according to claim 1, characterized in that it is the leuco compound 3,6-bis (dimethylamino) - 9 - (p - dimethylamino) - phenylxanthate contains. 4. Layer according to claim 1, characterized in that it is used as a binder or cellulose contains a cellulose derivative. suffered O Bund «printer« i, »« rlin