US3645741A

US3645741A - Diazotype light-sensitive material for intermediate original

Info

Publication number: US3645741A
Application number: US389A
Authority: US
Inventors: Syuhei Shiraishi; Tadashi Saito
Original assignee: Ricoh Co Ltd
Current assignee: Ricoh Co Ltd
Priority date: 1969-01-09
Filing date: 1970-01-02
Publication date: 1972-02-29
Anticipated expiration: 1989-02-28
Also published as: DE2000819A1; GB1278640A; DE2000819B2; DE2000819C3; NL139398B; NL7000292A

Abstract

There is provided a diazotype light-sensitive material for intermediate original (or substitute original), the lightsensitive material being able to give a dye-image which is easy to see and has low transmission of ultraviolet rays. Said material contains derivative of 1-hydroxynaphthalene-3,8disulfonic acid as one coupling component together with diazonium compound in the light-sensitive layer.

Description

ilniied Siaies Paiem Shiraishi et a1.

[ Feb. 29, 1972 [54] DIAZGTYPIE LIGHT-SENSITIVE MATERIAL FOR INTERMEDIATE ORIGINAL [72] Inventors: Syuhei Shiraishi, Fujisawa-shi; Tadashi Saito, Yokohama-shi, both of Japan [30] Foreign Application Priority Data Jan. 9, 1969 Japan ..44/1786 [52] US. Cl ..96/91, 96/49 [51] Int. Cl ..G03c 1/58 [58] Field of Search ..96/9l,49,75

[56] References Cited UNITED STATES PATENTS 1,857,920 5/1932 Lantz ..96/91 2,970,909 2/1961 Slimowicz ..96/91 3,1 13,025 12/1963 Bialczak ..96/91 3,248,220 4/1966 Van Rhijn.. 96/49 X 3,406,071 10/1968 Sus et ..96/91 3,410,688 11/1968 Welch ..96/49 X 3,473,930 10/1969 Werner et al. ..96/49 X 2,537,098 l/1951 Sliikin et a1 ..96/91 FOREIGN PATENTS OR APPLICATIONS 937,510 9/1963 Great Britain .,96/9l Primary Examiner-Charles L. Bowers, Jr. Attorney-Burgess, Ryan & Hicks [57] ABSTRACT There is provided a diazotype light-sensitive material for intermediate original (or substitute original), the light-sensitive material being able to give a dye-image which is easy to see and has low transmission of ultraviolet rays. Said material contains derivative of 1-hydroxynaphthalene-3,8-disulfonic acid as one coupling component together with diazonium compound in the light-sensitive layer.

4 Claims, N0 Drawings DIAZOTYPE LKGHT-SENSHTHVE MATERIAL FOR HNTERMEDTATE ORIGINAL BACKGROUND OF THE INVENTION 1. Fieldof the Invention The present invention relates to a diazotype light-sensitive material for intermediate original.

2. Description of the Prior Art The intermediate original of this invention signifies an original which was produced by copying from the first original carrying a desired image and will be used as a substitute for the first original. Consequently, it is to be desired that the dye image of the intermediate original inhibits the transmission of the ultraviolet rays as much as possible. in addition, it is necessary that the dye-image of the intermediate original should be easy to see, since there are frequent occasions when something is written in it. It is understood that as a yellow dyestuff is an effective ultraviolet absorber, the intermediate original carrying a yellow dye-image may give copies having a dye-image of high density. However, the yellow dye-image is hard to see. So in order to minimize the transmission of the ultraviolet rays and to get the dye-image easy to see, the brown dyestuff has been added to the yellow dyestuff to produce a sepia dye-image in the prior art. This sepia dye-image, however, increases to some extent the transmission of the ultraviolet rays because of coexistence of the brown dyestuff in the dye-image. As the matter of fact, a black dye-image is best visible, but in order to produce it, the other dye-stuffs should be added and coexisted with the sepia dyestuff, resulting in further increase of the transmission of the ultraviolet rays. The dye-image thus produced is not advisable for the dye-image of the intermediate original.

Diazotype light-sensitive materials for intermediate original are disclosed in Japanese Patent Publication No. 5672/1966 and US. Pat. No, 3,1 13,025.

The aforesaid No. 5672/1966 discloses that derivatives of lhydroxynaphthalene-4-alkyl-8-sulfonic acid having the following general formula are used as a coupling component:

Said derivatives give a deep blue dye-image when coupled with diazonium compounds. However, as they have higher coupling activity than that of m,m-dihydroxydiphenol or mhydroxyphenylurea which are used as coupling components producing a yellow dye-image, a black dye-image cannot be obtained even when two types (blue and yellow) of the coupling components are simultaneously used.

On the other hand, U.S. Pat. No. 3,113,025 discloses the compounds of Naphthol AS type having the following general formula as coupling components producing a blue dye-image:

When this compound is used together with m,m'-dihydroxydiphenol, it may produce a black dye-image. However, as this compound absorbs highly the ultraviolet rays by itself, the transmission of the ultraviolet rays in the nonimage area of the light-sensitive material is reduced, and consequently copying time must be prolonged when said compound is used as a coupling component of the light-sensitive material for intermediate original.

lt is, therefore, an objectof the present invention to provide a diazotype light-sensitive material for intermediate original which gives a black dye-image having the low transmission of the ultraviolet rays.

SUMMARY OF THE INVENTION wherein X is hydrogen or an alkali metal, R is hydrogen, an alkyl group of from 1 to 4 carbon atoms, an aralkyl group, a cycloalkyl group, a hydroxylated alkyl group,

(n being an integer of from 2 to 8, R, and R being an alkyl group of from one to four carbon atoms or a hydroxylated lower alkyl group) or(CH' ),,R- (n being an integer of from 2 to 8, R being The diazotype light-sensitive material for intermediate original prepared by using said coupling component of this invention can give an intermediate original having a dye-image which is very visible and has the low transmission of the ultraviolet rays.

Moreover, we have found that the above-mentioned compounds, in which sulfonic acid group has been introduced in the 4-position in lieu of 3-position, have disadvantages that they give a dark blue dyestuff when coupled with diazonium compounds, but the density of the dye-image obtained from them is lower than that of a dye-image obtained from the above-mentioned compounds of this invention and the color tone of the dye-image is easy to change after development in ammonia vapor.

Derivatives of monohydric phenol, which may be used together with the aforementioned coupling components and may produce a yellow azo dyestuff by coupling with dizzonium compound, are as follows:

2-(N N'-diethylaminomethyi)-3,o-dimethylphenol, m-

acetamino-phenol, m-hydroxyethylphenol, a-hydroxyphenylurea, m-hydroxyphenylurea, 3,3-dihydroxycarbanilide, m,m-ethylene-dioxydiphenol, m,m'- trimethylenedioxydiplrenol, m,mtetra-methylenedioxydiphenol, 6,6 '-dimethyl-3 ,3-trimethylenedioxydiphenol.

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention is further illustrated by the following nonlimitative examples.

EXAMPLE 1 A light-sensitive solution was prepared from the following ingredients:

methyl cellosolvc l00.0 cc. cellulose acetate butyrate 2.0 g. sull'osalicylic acid 1.5 g. zinc chloride 0.2 g. m-hydroxyphenylurea 1.5 g. 3-sulfonic acid (sodium salt)-l-hydroxynaphthalenc -8-sulfonic acid amide 0.45 g. p-morpholinobenzene diazoninm-BF 1.3 g.

A light-sensitive material for intermediate original was obtained by applying said light-sensitive solution to a surface of a substrate made of cellulose triacetate and then drying off.

This light-sensitive material gave an intermediate original having a deep greenish black dye-image by closely overlaying it on the original carrying a desired image, and exposing to the ultraviolet light and then developing in ammonia vapor.

On the contrary, a light-sensitive material was obtained by the same procedure except that 0.4 g. of 3,3-dihydroxy-2- naphthoanilide (described in U.S. Pat. No. 3,1 13,025) was employed as a substitute for 0.45 g. of said 3-sulfonic acid (sodium salt) -l-hydroxynapthalene -8-sulfonic acid amide. This light-sensitive material gave a reddish half-tone dyeimage and a slow copying speed by about 30 percent in comparison with the above-mentioned material.

EXAMPLE 2.

A light-sensitive material for intermediate original was obtained by repeating the procedure of Example 1 except that 2.0 g. m,m-ethylenedioxydiphenol was employed as a substitute for m-hydroxyphenylurea. This light-sensitive material possessed the same properties as that of Example 1.

EXAMPLE 3 A light-sensitive material for intermediate original was obtained by repeating the procedure of Example l except that 0.55 g. of 3-sulfonic acid (sodium salt)-l-hydroxynaphthalene-S-sulfonic acid butyramide was employed as a substitute for 0.45 g. 3-sulfonic acid (sodium salt)-l-hydroxynaphthalene-B-sulfonic acid amide. This light-sensitive material possessed the same properties as that of Example 1.

EXAMPLE 4 A light-sensitive solution was prepared from the following ingredients:

A light-sensitive material for intermediate original was obtained by repeating the procedure of Example 1 except that said sensitive solution was employed. This light-sensitive material gave an intermediate original having a blaclr dyeimage by treating it in the same manner as that of Example I.

EXAMPLE 5 A light-sensitive solution was prepared from the following ingredients:

A precoat solution was prepared from the following ingredients:

copolymer of vinyl acetate and crotonic acid I 10.0 g. urea-formaldehyde resin l0.0 g. fine grain silica 5.0 g.

I000 cc.

methyl cellosolve A light-sensitive material for intermediate original was obtained by applying said light-sensitive solution to a substrate made of polyester, precoated with said precoat solution, and drying off. This light-sensitive material gave an intermediate original having a black dye-image by treating it in the same manner as that of Example 1. The intermediate original thus obtained gave a nice copy by using it as an original.

We claim:

1. A diazotype light-sensitive material comprising a support having a light-sensitive layer thereon said light sensitive layer comprising a diazonium compound and a mono-hydric phenol as one coupling component and as a second coupling component, a derivative of l-hydroxynaphthtalene-3,8-disulfonic acid having the following formula:

XOaS- n being an integer of from 2 to 4 and R, and R each being an alkyl group of from one to four carbon atoms, and an acidic stabilizer.

2. A light-sensitive material according to claim 1 wherein the derivative of l-hydroxynaphthalene-3,8-disulfonic acid is the sodium salt of 3-sulfonic acid-l-hydroxynaphthalene-8- sulfonic acid amide.

3. A light-sensitive material according to claim 1 wherein the derivative of l-hydroxynaphthalene-3,8-disulfonic acid is 3-..ulfonic acid- 1 -hyd roxynaphthalene-8-B-diethylam inoethylsulfonic acid amide.

4. A light-sensitive material according to claim 1 wherein the derivative of 1-hydroxynaphthalene-3,8-disulfonic acid is 3-sulfonic acid- 1 -hydroxynaphthalene-8 -sulfonic acid methylamide.

Claims

2. A light-sensitive material according to claim 1 wherein the derivative of 1-hydroxynaphthalene-3,8-disulfonic acid is the sodium salt of 3-sulfonic acid-1-hydroxynaphthalene-8-sulfonic acid amide.
3. A light-sensitive material according to claim 1 wherein the derivative of 1-hydroxynaphthalene-3,8-disulfonic acid is 3-sulfonic acid-1-hydroxynaphthalene-8- Beta -diethylamino-ethylsulfonic acid amide.
4. A light-sensitive material according to claim 1 wherein the derivative of 1-hydroxynaphthalene-3,8-disulfonic acid is 3-sulfonic acid-1-hydroxynaphthalene-8-sulfonic acid methylamide.