US3740229A - Diazotype photographic copying material for heat development - Google Patents

Diazotype photographic copying material for heat development Download PDF

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Publication number
US3740229A
US3740229A US00133442A US3740229DA US3740229A US 3740229 A US3740229 A US 3740229A US 00133442 A US00133442 A US 00133442A US 3740229D A US3740229D A US 3740229DA US 3740229 A US3740229 A US 3740229A
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United States
Prior art keywords
diazo
light
acid
sensitive layer
copying material
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Expired - Lifetime
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US00133442A
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English (en)
Inventor
S Maruyama
E Oida
T Hamada
T Asami
S Iwata
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Ricoh Co Ltd
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Ricoh Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/58—Coupling substances therefor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis

Definitions

  • a diazotype photographic copying material that is heat developable is comprised of a support having formed thereon a light-sensitive layer consisting essentially of a light-sensitive diazonium compound and an azo dye coupler consisting of a polyhydroxybenzoic acid compound.
  • the present invention relates to a heat developable diazotype copying material.
  • the known diazotype photographic copying materials which are heat developable have the advantages of ease of handling during the reproduction process, yet they possess a number of inherent disadvantages.
  • the lightsensitive layers of the conventional heat developable diazotype copying materials necessarily contain all the components of reaction that participate in the development of color. This is a major disadvantage and commonly leads to premature reaction during storage, causing the known phenomenon of fogging. Moreover, these components of reaction are necessarily heat responsive, and are hence prone to deterioration at elevated storage temperatures.
  • the heat developable copying materials that have been in use up to this time are consistently designed to function by producing colored images through the action of a base, released during heat development, and contain in the light-sensitive layer a base-generating agent such as urea or an alkali metal salt of an organic acid to effect the azo coupling in an alkaline environment, said environment being generated during the process of heat development.
  • a base-generating agent such as urea or an alkali metal salt of an organic acid to effect the azo coupling in an alkaline environment, said environment being generated during the process of heat development.
  • the loss of urea tnd similar substance from the light-sensitive layer to the support is likely to occur during storage, causing deterioration in image-forming qualities after storage, usually manifested by reduced color density of the copied image. Attempts to compensate for this loss by using excessive amounts of urea or the like in the light-sensitive layer have led to extremely undesirable soiling or fouling of the copying equipment, especially during continuous operation.
  • This invention provides a diazotype photographic copying material, an article of manufacture that is heat developable having improved shelf life and stability of copied image by means of the inclusion in the lightsensitive layer of said material a novel coupler component, a hydroxybenzoic acid compound of the formula HO OH in which R R and R are selected from the substituents selected from the groups tabulated below and used in the combinations of R R and R as tabulated below.
  • alkylamincs [(6- hydi'oxyethyl) amino] methyl radical and morpholino lower alkyl radicals, wherein the alkyl has 1-6 carbon atoms.
  • 4-acetylresorcin is prepared, according to Hoesch' 15 synthesis method, from resorcin as the starting material.
  • This 4-acetylresorcin is subjected to Clemensen reduction to synthesize 4-ethylresorcin. Then, a mixture consisting of 1.0 part by weight of this 4-ethylresorcin, 1.5 parts by weight of potassium bicarbonate and 1.0 part by Weight of 20 Water is subjected to reaction therebetween in a carbon dioxide gas atmosphere and at a temperature ranging from 120 C. to 130 C. for 3 hours in an autoclave. The resulting product is then dissolved in water.
  • the insolu- Compound 1 2 Ra 3-chloro-4methylw-resorcylic acid C1 CHa -H 3,5-dichl0r0-4rmcthyl'y-resorcy].ic acid.
  • a resorcin or a phloroglucin compound is heated, together with an alkali metal carbonate, in water or in an inert solvent such as dimethylformamide, in a gaseous carbon dioxide atmosphere to introduce the carboxyl radical.
  • the compound can then be halogenated with a halogenating agent such as idoine chloride, bromide or sulfuryl chloride in a solvent such as diethyl ether or glacial acetic acid.
  • the color portion of the copied image using an iron chloride agent, of any one of the novel couplers described above is invariably blue.
  • the couplers of this invention are insoluble or difficultly soluble in water, but it can be rendered water-soluble by using as a solubilizing agent an alkali metal carbonate, e.g. sodium or potassium citrate or acetate, or guanidine carbonate. These agents can therefore be used to facilitate the preparation of the solutions for use in the formation of light-sensitive layers acs rd s to h s invention.
  • phloroglucin 1.0 part by weight of phloroglucin is dissolved in an aqueous solution of percent caustic soda. While gradually introducing, in drops, a total of 1.3 parts by weight of dimethyl sulfuric acid into the resulting solu tion at 40 C., the resulting mixed solution is allowed to react for 2 hours. Then, the resultant reaction product (oily matter) is subjected to fractional distillation under a reduced pressure, with a result that phloroglucin monomethylether having a boiling point ranging from 180 C. to 185 C. at a pressure ranging from 7 to 8 mm. Hg is distilled outwith a yield of 0.48 part by weight.
  • the polyhydroxy benzoic acid derivative obtained, for example, in the foregoing manner can be admixedas the coupler component-in the light-sensitive layer of a diazotype photographic copying material intended for heat development to thereby eliminate the various drawbacks of the copying materials of this type of the prior art.
  • the components other than said coupler component of the light-sensitive layer can be any of those materials that have been used in the formation of the light-sensitive layers of the copying materials of the prior art.
  • typical diazo compounds which are suitable for use with the coupler component of this invention are:
  • these diazo compounds can be used, in general, in the form of a double salt of such diazo compound and a metal chloride such as zinc chloride and cadmium chloride.
  • the present invention includes the optional use of a color development accelerator in the components which constitute the light-sensitive layers of the copying materials.
  • a color development accelerator which is particularly suitable for these purposes includes urea, its derivatives-such as methylureaand also includes thiourea and its derivatives.
  • organic acid amides such as benzamide, crotonamide and malonamide, and polyhydroxy compounds, such as sorbitol, mannitol and pentaerythritol, are also suitable.
  • the employment of metal salts of organic as well as inorganic acids such as zinc acetate, aluminum chloride, cadmium sulfate, cadmium nitrate and cadmium chloride is suitable also.
  • a xanthine compounds uch as cafieine, theophilline and theobromine to the solution with which a light-sensitive layer is formed is effective in arresting the production of preciptates arising from possible reaction between the diazo compound and the coupler component, or in other words, such an addition of a xanthine compound is effective in suppressing such an undesirable reaction.
  • a solution for forming a light-sensitive layer is prepared by dissolving or dispersing, in water, the respective light-sensitive layer components which have been already described, and by applying this solution onto one face of a support and thereafter drying the same, whereby there is obtained a desired diazotype photographic copying material adapted for heat development.
  • the desirable proportion of the coupler component consisting of polyhydroxy benzoic acid compound to the diazo compound is such that the amount of the coupler component is in the range of from 1.0 to 10.0 parts by weight to 1.0 part by weight of the diazo compound.
  • the color development accelerator which is another material for forming the light-sensitive layer is mixed in an amount in the range of from 0.1 to 10.0 parts by weight to 1.0 parts by weight of the diazo compound.
  • the desired amount of the aforesaid metal salt which is mixed and which is capable of preventing said fog phenomenon ranges from 0.1 to 3.0 parts by weight to 1.0 part by weight of the diazo compound.
  • the desired amount of the aforesaid xanthine compound which is admixed at the time of preparing the solution for forming a light-sensitive layer is in the range of from 0.5 to 10.0 parts by weight to 1.0 part by weight of said diazo compound contained in said lightsensitive layer.
  • the color development accelerator, metal salt and xanthine compound as described above are all assistant components or optional ingredients for constituting the light-sensitive layers of the copying materials, and it is preferable in the case of the present invention to use one or two and more of these components together with the diazo compound and the coupler component.
  • a light-sensitive layer having a composition consisting of the aforesaid proportions will achieve effectively the objects of the present invention.
  • Example 1 Onto a support having a precoated layer containing silica and starch was applied a light-sensitive solution of the following composition and the resultant support was dried to obtain a diazotype photographic copying material.
  • Example 2 Onto a support similar to that used in Example 1 was applied a light-sensitive solution according to Example 1 wherein the coupler and diazo compound were replaced with 3-bromo-4-methoxy-v-resorcylic acid (2.0 gr.) and 4-diazo-N-propyl-N-ethylaniline zinc chloride double salt (0.8 gr.), and the resultant support was dried to obtain a diazotype photographic copying material.
  • the assistants other than above compounds were the same as those used in Example 1.
  • the said copying material was subjected to the same procedure as that of Example 1.
  • the developed image was noted to be blue in color.
  • Example 3 A solution for forming a light-sensitive layer and having the followi g compo tion
  • Example 4 Onto a support similar to that used in Example 1 was applied a light-sensitive solution according to Example 1 wherein the coupler and diazo compound were replaced with 3-ethyl-5-bromo-'y-resorcyclic acid (2.0 gr.) and 4- diazo-N,N-dipropyl aniline zinc chloride double salt (0.8 gr.), and the resultant support was dried to obtain a diazotype photographic copying material.
  • the assistants other than above compounds were the same as those used in Example 1.
  • the said copying material was subjected to the same procedure as that of Example 1.
  • the developed image was noted to be blue in color.
  • Example 5 Onto a support similar to that used in Example 1 was applied a light-sensitive solution according to Example 4 wherein only the coupler was replaced with 3,5-dibromo- 4-methoxy-y-resorcylic acid (2.0 gr.), and the resultant support was dried to obtain a diazotype photographic copying material.
  • the assistants and diazonium compound other than above compound were the same as those used in Example 4.
  • the said copying material was subjected to the same procedure as that of Example 1.
  • the developed image was noted to be blue in color.
  • Example 6 Onto a support similar to that used in Example 1 was applied a light-sensitive solution according to Example 1 wherein the coupler and diazo compound were replaced wtih 3,S-diiodo-4-ethoxy- -resorcylic acid (2.0 gr.) and 4-diazo-2,5-diethoxy-1-morpholinobenzene zinc chloride double salt (0.8 gr.), and the resultant support was dried to obtain a diazotype photographic copying material.
  • the assistants other than above compounds were the same as those used in Example 1.
  • the said copying material was subjected to the same procedure as that of Example 1.
  • the developed image was noted to be blue in color.
  • Example 7 Onto a support similar to that used in Example 1 was applied a light-sensitive solution according to Example 1 wherein only the coupler was replaced with B-(methyl) amino-'y-resorcylio acid (2.0 gr.), and the resultant support was dried to obtain a diazotype photographic copying material.
  • the assistants and diazonium compound other than above compound are the same as those used in Example 1.
  • the said copying material was subjected to the same procedure as that of Example 1.
  • the developed image was noted to be blue violet in color.
  • Example 8 Onto a support similar to that used in Example 1 was applied a, light-sensitive solution according to Example 1 9 wherein the coupler and diazo compound were replaced with 3-(methyl)amino-S-bromo-y-resorcylic acid (2.0 gr.) and 4-diazo-N-cyclohexyl-N-benzylaniline zinc chloride double salt (0.8 gr.), and the resultant support was dried to obtain a diazotype photographic copying material.
  • the coupler and diazo compound were replaced with 3-(methyl)amino-S-bromo-y-resorcylic acid (2.0 gr.) and 4-diazo-N-cyclohexyl-N-benzylaniline zinc chloride double salt (0.8 gr.)
  • a diazotype photographic copying material for heat development which comprises a support having formed thereon a light-sensitive layer comprising a light-sensitive diazonium compound and an azo coupling component selected from the group consisting of compounds having the formula HO OH in which R is selected from the group consisting of H, Cl, Br, I and alkyl having from 1 to 6 carbon atoms; R; is selected from the group consisting of alkyl and alkoxy having from 1 to 6 carbon atoms; and R is selected from the group consisting of H, Cl, Br and I; and wherein at least one of R and R is Cl, Br and I.
  • a diazotype photographic copying material for heat development which comprises a support having formed thereon a light-sensitive layer comprising a light-sensitive diazonium compound and an azo coupling component selected from the group consisting of compounds having the formula (IJOOH HO OH Ra Rx in which R is alkyl having from 1 to 6 carbon atoms; R is H; and R is selected from the group consisting of H, Cl, Br and I.
  • a diazotype photographic copying material for heat development which comprises a support having formed thereon a light-sensitive layer comprising a light-sensitive diazonium compound and an azo coupling component selected from the group consisting of compounds having the formula in which R is selected from the group consisting of alkylamino wherein the alkyl has from 1 to 6 carbon atoms (B-hydroxyethyl), amino methyl and morpholinoalkyl wherein the alkyl has from 1 to 6 carbon atoms; R is H; and R is selected from the group consisting of H, Cl, Br and I.
  • the light-sensitive layer further contains at least one assistant component selected from the group consisting of a color development accelerator, a metal salt and a Xanthine compound
  • said color development accelerator being selected from the group consisting of urea, methylurea, thiourea, benzamide, crotonamide, malonamide, sorbitol, mannitol and pentaerythritol
  • said metal salt being selected from the group consisting of zinc acetate, aluminum chloride, cadmium sulfate, cadmium nitrate and cadmium chloride
  • said xanthine compound being selected from the group consisting of caffeine, theophilline and theobromine.
  • a diazotype photographic copying material according to claim 1, wherein said light-sensitive diazonium compound is one member selected from the group consisting of;
  • a diazotype photographic copying material wherein the amount of said azo dye coupler contained in said light-sensitive layer is in the range of from 1.0 to 10.0 parts by weight per 1.0 part by Weight of said light-sensitive diazonium compound contained in said light-sensitive layer.
  • a diazotype photographic copying material wherein the amount of said color development accelerator contained in said light-sensitive layer is in the range of from 0.1 to 10.0 parts by weight per 1.0 part by weight of said light-sensitive diazonium compound contained in said light-sensitive layer, the amount of said metal salt contained in said light-sensitive layer is in the range of from 0.1 to 3.0 parts by weight per 1.0 part by weight of said light-sensitive diazonium compound contained in said light-sensitive layer and the amount of said Xanthine compound contained in said light-sensitive layer is in the range of from 0.5 to 10.0 parts by Weight per 1.0 part by weight of said light-sensitive diazonium compound contained in said light-sensitive layer.
  • the light-sensitive layer further contains at least one assistant component selected from the group consisting of a color development accelerator, a metal salt and a xanthine compound
  • said color development accelerator being selected from the group consisting of urea, methylurea, thiourea, benzamide, crotonamide, malonamide, sorbitol, mannitol and pentaerythritol
  • said metal salt being selected from the group consisting of zinc acetate, aluminum chloride, cadmium sulfate, cadmium nitrate and cadmium chloride
  • said xanthine compound being selected from the group consisting of caffeine, theophilline and theobromine.
  • a diazotype photographic copying material according to claim 2, wherein said light-sensitive diazonium compound is one member selected from the group consisting of:
  • a diazotype photographic copying material wherein the amount of said azo dye coupler contained in said light-sensitive layer is in the range of from 1.0 to 10.0 parts by weight per 1.0 part by weight of said light-sensitive diazonium compound contained in said light-sensitive layer.
  • a diazotype photographic copying material wherein th amount of said color development accelerator contained in said light-sensitive layer is in the range of from 0.1 to 100 parts by weight per 1.0 part by Weight of said light-sensitive diazonium compound contained in said light-sensitive layer, the amount of said metal salt contained in said light-sensitive layer is in the range of from 0.1 to 3.0 parts by weight per 1.0 part by Weight of said light-sensitive diazonium compound contained in said light-sensitive layer and the amount of said Xanthine compound contained in said light-sensitive layer is in the range of from 0.5 to 10.0 parts by weight per 1.0 part by weight of said light-sensitive diazonium compound contained in said light-sensitive layer.
  • a diazotype photographic copying material in which the light-sensitive layer further contains at least one assistant component selected from the group consisting of a color development accelerator, a metal salt and a Xanthine compound, said color develop ment accelerator being selected from the group consisting of urea, methylurea, thiourea, benzamide, crotonamide, malonamide, sorbitol, mannitol and pentaerythritol, said metal salt being selected from the group consisting of zinc acetate, aluminum chloride, cadmium sulfate, cadmium nitrate and cadmium chloride and said xanthrine compound being selected from the group consisting of caffeine, theophilline and theobromine.
  • assistant component selected from the group consisting of a color development accelerator, a metal salt and a Xanthine compound
  • said color develop ment accelerator being selected from the group consisting of urea, methylurea, thiourea, benzamide, crot
  • a diazotype photographic copying material according to claim 3, wherein said light-sensitive diazonium compound is one member selected from the group consisting of:
  • a diazotype photographic copying material wherein the amount of said azo dye coupler contained in said light-sensitive layer is in the range of from 1.0 to 10.0 parts by weight per 1.0 part by weight of said light-sensitive diazonium compound contained in said light-sensitive layer.
  • a diazotype photographic copying material wherein the amount of said color development accelerator contained in said light-sensitive layer is in the range of from 0.1 to 10.0 parts by weight per 1.0 part by weight of said light-sensitive diazonium compound contained in said light-sensitive layer, the amount of said metal salt contained in said light-sensitive layer is in the range of from 0.1 to 3.0 parts by Weight per 1.0 part by Weight of said light-sensitive diazonium compound contained in said light-sensitive layer and the amount of said Xanthine compound contained in said light-sensitive layer is in the range of from 0.5 to 10.0 parts by weight per 1.0 part by weight of said light-sensitive diazonium compound contained in said light-sensitive layer.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00133442A 1967-03-07 1971-04-12 Diazotype photographic copying material for heat development Expired - Lifetime US3740229A (en)

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JP1429567 1967-03-07

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US (1) US3740229A (https=)
DE (1) DE1622939C3 (https=)
FR (1) FR1559267A (https=)
GB (1) GB1226373A (https=)
NL (1) NL6803228A (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4421839A (en) * 1979-08-03 1983-12-20 Dai Nippon Printing Co., Ltd. Heat-sensitive and photofixing recording sheet with diazosulfonate and acidic coupling agent therefore
US5494772A (en) * 1992-03-06 1996-02-27 Fuji Photo Film Co., Ltd. Heat-sensitive recording materials for infrared-laser recording comprising tricarbocyanine dye having at least two acidic groups

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1292607A (en) * 1968-12-28 1972-10-11 Ricoh Kk Improvements in and relating to heat-developable light-sensitive material
WO1980001918A1 (en) * 1979-03-09 1980-09-18 A Hawkes Polymer,preparation and formulations for preparation thereof use for production of bonded materials,intermediates and preparation thereof
FR2670205A1 (fr) * 1990-12-06 1992-06-12 Rhone Poulenc Agrochimie 2,6-alkoxypenyl alkylcetone et derives herbicides.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4421839A (en) * 1979-08-03 1983-12-20 Dai Nippon Printing Co., Ltd. Heat-sensitive and photofixing recording sheet with diazosulfonate and acidic coupling agent therefore
US5494772A (en) * 1992-03-06 1996-02-27 Fuji Photo Film Co., Ltd. Heat-sensitive recording materials for infrared-laser recording comprising tricarbocyanine dye having at least two acidic groups

Also Published As

Publication number Publication date
DE1622939B2 (de) 1974-01-24
GB1226373A (https=) 1971-03-24
NL6803228A (https=) 1968-09-09
DE1622939C3 (de) 1974-08-15
DE1622939A1 (de) 1971-12-09
FR1559267A (https=) 1969-03-07

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