JPH04340541A - Photosensitive and heat-sensitive recording material - Google Patents

Abstract

PURPOSE:To obtain the recording material which is improved in the uniformity of a color developing layer and has less surface fogging by forming a coupling component of the cyclic ester deriv. of malonic acid. CONSTITUTION:A layer contg. the 1,3-dioxane-4,6-dione deriv. substd. in the 2-position, a diazo compd. and an org. base is provided on a base. The 1,3- dioxane-4,6-dione deriv. expressed by formula I is preferable. In the formula, R1 and R2 may be the same or different and denote a hydrogen atom, alkyl group which can be substd. and aryl group which can be substd. The coupling component to be used may be used by dispersing in a solid form together with a basic material and other developing assistants, etc., into a water-soluble high polymer by a sand mill, etc., and is particularly excellent for purposes of being used in the form of an emulsion together with suitable emulsification assistants, etc. The preferable water-soluble high polymer includes a water-soluble high polymer used at the time of preparing microcapsules.

Description

[Detailed description of the invention]

0001

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a recording material that utilizes the photosensitivity of a diazo compound (diazonium salt), and more particularly to a red-color-producing light- and heat-sensitive recording material.

0002

BACKGROUND OF THE INVENTION Three types of recording materials utilizing the photosensitivity of diazo compounds are known. One type is known as a wet development type, in which a photosensitive layer containing a diazo compound and a coupling component as main components is provided on a support, this material is superimposed on the original, and after exposure, it is processed in an alkaline solution. It is to be developed. The second type is known as a dry development type, which, unlike the wet type, develops with ammonia gas. The third type is known as a heat-developable type, and includes a type that contains an ammonia gas generating agent such as urea that can generate ammonia gas when heated in the photosensitive layer, or a type that contains an ammonia gas generating agent such as urea that can generate ammonia gas when heated, or a type that contains ammonia gas generating agent such as trichloroacetic acid in the photosensitive layer. There are types that contain an alkali salt of an acid that loses its properties as an acid when heated, and types that use a higher fatty acid amide as a coloring aid and activate the diazo compound and coupling component by heating and melting.

[0003] In addition to maintenance problems such as the need for replenishing and discarding the liquid because it uses a developing solution and the large size of the device, the wet type also has problems with maintenance, such as the fact that the image is wet immediately after copying, making it difficult to make additions immediately. There are some problems, such as not being able to store images, or copy images not being able to withstand long-term storage. Also, like the wet type, the dry type requires replenishment of developer.
In addition to the need for gas absorption equipment to prevent the generated ammonia gas from leaking to the outside, and the increased size of the device, there are also other problems such as the smell of ammonia immediately after copying. On the other hand, unlike the wet and dry types, the heat-developable type has the advantage of maintenance because it does not require a developing solution. Moreover, if the temperature is not controlled to about ±10° C., insufficient development or changes in color tone occur, resulting in an increase in equipment cost. Furthermore, the diazo compound used for such high-temperature development is required to have high heat resistance, but such compounds are often disadvantageous in forming high concentrations. Low temperature development (90°C
-130°C), but these had the drawback of decreasing the shelf life of the material itself. As described above, although the thermal development type is expected to have sufficient advantages in terms of maintenance compared to the wet and dry types, the current situation is that it has not yet become the mainstream of diazo recording systems. Now, in order to obtain the desired color density by heating a material in which a layer containing a diazo compound and a coupling component is provided on a support, heating causes each component to instantly melt, diffuse, and
Although it is necessary to react to produce a coloring dye, it is preferable to make the system basic during this reaction since this has the effect of accelerating the reaction. Therefore, in order to produce a light- and heat-sensitive recording material having a recording speed that does not pose a practical problem when heated at low temperatures, it is essential to include a basic substance in the coating layer.

[0004] On the other hand, it is also essential for light and heat sensitive recording materials to suppress as much as possible the background coloring and the decrease in color density during storage before copying. Although the above-mentioned several attempts have been made to create photosensitive and thermosensitive recording materials that have a good shelf life and a high recording speed, the current situation is that they have not yet reached the point where they can be put to practical use. If we design a material that can sufficiently develop color and obtain a high concentration even at low heating temperatures, it is natural that a color reaction may occur even while it is stored at room temperature before copying. This appears as a phenomenon in which the bare skin becomes colored. especially,
In the case of red coloring type recording materials, there is a problem in that even slight coloring (fogging) of the background becomes noticeable due to high visibility. In order to solve these seemingly incompatible problems, the inventors of the present invention made extensive studies and found that a recording material in which a heat-developable photosensitive layer containing a diazo compound, a coupling component, and a basic substance is provided on a support. By incorporating the diazo compound into microcapsules, we continued to investigate basic substances, how to make microcapsules, etc., and succeeded in suppressing skin discoloration during storage before copying. (Unexamined Japanese Patent Publication No. 2-54251) However, the cyclohexane-1,3-dione derivative, which is the coupling component described in the above patent, actually has low oil solubility, and the storage stability of the recording material after emulsification and dispersion is poor. This proved to be unfavorable, necessitating the development of a coupling component that improved the stability of the dispersion.

[0005]

[Problems to be Solved by the Invention] Therefore, the first aspect of the present invention
An object of the present invention is to provide a light and heat sensitive recording material in which the uniformity of the coloring layer is improved by using a coupling component with improved oil solubility. A second object of the present invention is to provide a light and heat sensitive recording material with less background fog.

[0006]

[Means for Solving the Problems] The above objects of the present invention are as follows:
A photosensitive and thermosensitive recording material comprising a recording layer containing a diazo compound, a coupling component, and an organic base provided on a support, wherein the coupling component is a cyclic ester derivative of malonic acid. achieved by the material.

Among the cyclic ester derivatives of malonic acid according to the present invention, 1,3-dioxane-4,6-dione derivatives are preferred, and from the viewpoint of oil solubility, the 2-position is preferably substituted. From the viewpoint of coupling activity with a diazo compound, it is preferable that the 5-position is unsubstituted.

Among the cyclic ester derivatives of malonic acid according to the present invention, compounds represented by the following general formula (1) are preferred. General formula (1)

[0009]

[Chemical formula 1]

(In the above formula, R1 and R2 may be the same or different and represent a hydrogen atom, a substitutable alkyl group, or a substitutable aryl group.)

In general formula (1), R1 and R2
Among the groups represented by, hydrogen atoms, alkyl groups having 1 to 30 carbon atoms, and aryl groups having 6 to 40 carbon atoms are preferred. In particular, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms,
An aryl group having 6 to 30 carbon atoms is preferred. These groups may further have a substituent, and examples of the substituent include an alkyl group, an alkoxy group, a polyfluoroalkyl group, a halogen atom, an aryl group, an aryloxy group, an alkylthio group, an arylthio group, an acylamino group, and a dialkyl group. An amino group is preferred.

[0012] R1 and R2, R2 and R3, R3
and R4, R4 and R5, and R5 and R6 may be bonded to each other to form a ring containing a heteroatom.

Specific examples of the coupling components according to the present invention are shown below, but the present invention is not limited thereto. 2,2-dimethyl-1,3-dioxane-4,6-dione, 2-methyl-2-ethyl-1,3-dioxane-4
, 6-dione, 2-methyl-2-butyl-1,3-dioxane-4,6-dione, 2-methyl-2-phenyl-
1,3-dioxane-4,6-dione, 2-methyl-2
-(4-methoxyphenyl)-1,3-dioxane-4
,6-dione, 2,2-bis(4-dimethylaminophenyl)-1,3-dioxane-4,6-dione, 2-methyl-2-(4-ethoxyphenyl)-1,3-dioxane -4,6-dione, 2-methyl-2-(4-butoxyphenyl)-1,3-dioxane-4,6-dione,
2-Methyl-2-(4-hexyloxyphenyl)-1
, 3-dioxane-4,6-dione, 2-methyl-2-
(4-octyloxyphenyl)-1,3-dioxane-4,6-dione, 2-methyl-2-(4-decyloxyphenyl)-1,3-dioxane-4,6-dione,
2-Methyl-2-[(2-ethylhexyloxy)phenyl]-1,3-dioxane-4,6-dione, 2-methyl-2-(4-dodecyloxyphenyl)-1,3-
Dioxane-4,6-dione, 2-phenyl-2-(4
-hexyloxyphenyl)-1,3-dioxane-4
, 6-dione, 2-phenyl-2-(4-octyloxyphenyl)-1,3-dioxane-4,6-dione,
2-phenyl-2-(4-dodecyloxyphenyl)-
1,3-dioxane-4,6-dione, 2-methyl-2
-(2-octyloxyphenyl)-1,3-dioxane-4,6-dione, 2-methyl-2-(3-hexyloxyphenyl)-1,3-dioxane-4,6-dione, 2 -Phenyl-2-(2-octyloxyphenyl)-1,3-dioxane-4,6-dione, 2-phenyl-1,3-dioxane-4,6-dione, 2-butyl-1,3- Dioxane-4,6-dione, 2-hexyl-1,3-dioxane-4,6-dione, 2-(2-methoxyphenyl)-1,3-dioxane-4,6-dione, 2-(2 -butoxyphenyl)-1,3-dioxane-4,6-dione, 2-(2-hexyloxyphenyl)-1,3-dioxane-4,6-dione, 2-(2-hexyloxyphenyl)-1,3-dioxane-4,6-dione,
-octyloxyphenyl)-1,3-dioxane-4
, 6-dione, 2-(2-decyloxyphenyl)-1
, 3-dioxane-4,6-dione, 2-(2-dodecyloxyphenyl)-1,3-dioxane-4,6-dione, 2-(2-tetradecyloxyphenyl)-1,
3-dioxane-4,6-dione, 2-(4-methoxyphenyl)-1,3-dioxane-4,6-dione, 2
-(4-butoxyphenyl)-1,3-dioxane-4
, 6-dione, 2-(4-hexyloxyphenyl)-
1,3-dioxane-4,6-dione, 2-(4-octyloxyphenyl)-1,3-dioxane-4,6-
Dione, 2-(3-octyloxyphenyl)-1,3
-Dioxane-4,6-dione, 2-(2,4-dibutoxyphenyl)-1,3-dioxane-4,6-dione, 2-(3,4-dibutoxyphenyl)-1,3 -dioxane-4,6-dione, 2-(3-methoxy-4-octyloxyphenyl)-1,3-dioxane-4,6
-dione, 2-(2-methoxy-4-octyloxyphenyl)-1,3-dioxane-4,6-dione, and the like.

The diazo compound and the coupling component contained in the photosensitive layer of the present invention come into contact with each other and react with each other to develop color when heated. A photodegradable compound is used which decomposes when exposed to heat. The photodegradable diazo compound as used in the present invention mainly refers to aromatic diazo compounds, and more specifically refers to aromatic diazonium salts, diazosulfonate compounds, and diazoamino compounds. It is generally said that the photodecomposition wavelength of a diazo compound is its maximum absorption wavelength. Further, it is known that the absorption maximum wavelength of a diazo compound varies from about 200 nm to about 700 nm depending on its chemical structure. ("Photodecomposition and chemical structure of photosensitive diazonium salts" by Takahiro Tsunoda and Akio Yamaoka, Journal of the Photographic Society of Japan 29 (4) pp. 197-205 (1965)) That is, when a diazo compound is used as a photodegradable compound,
It breaks down with light of a specific wavelength depending on its chemical structure. or,
By changing the chemical structure of the diazo compound, it is possible to change the hue of the dye after the reaction even when the diazo compound undergoes a coupling reaction with the same coupling component.

The diazo compound is a compound represented by the general formula (2). General formula (2) Ar-N2 + X- (wherein, Ar represents a substituted or unsubstituted aromatic ring, and N2
represents a diazonium group, and X represents an acid anion. )

[
Specific examples of the diazo compound used in the present invention include the following. 4-diazo-1-dimethylaminobenzene, 4-diazo-2-butoxy-5-chloro-1-dimethylaminobenzene, 4-diazo-1-methylbenzylaminobenzene 4-diazo-1-ethylhydroxyethylaminobenzene, 4-diazo-1-diethylamino-3-methoxybenzene, 4-diazo-1-morpholinobenzene, 4-diazo-1-morpholino-2,5-dibutoxybenzene,
4-Diazo-1-tolylmercapto-2,5-diethoxybenzene, 4-diazo-1-piperazino-2-methoxy-5-chlorobenzene, 4-diazo-1-(N,N
-dioctylaminocarbonyl)benzene, 4-diazo-1-(4-tert-octylphenoxy)benzene, 4-diazo-1-(2-ethylhexanoylpiperidino)-2,5-dibutoxybenzene, 4- Diazo-1-
(2,5-di-tert-amylphenoxy-α-butanoylpiperidino)benzene, 4-diazo-1-(4-
methoxy)phenylthio-2,5-diethoxybenzene, 4-diazo-1-(4-methoxy)benzamide-2
, 5-diethoxybenzene, 4-diazo-1-pyrrolidino-2-methoxybenzene

Specific examples of acids that form diazonium salts with the above-mentioned diazo compounds include the following. Cn F2n+1COOH (n is an integer from 1 to 9), Cm
F2m+1SO3H (m is an integer from 1 to 9), boron tetrafluoride, tetraphenylboron, hexafluorophosphoric acid, aromatic carboxylic acid, aromatic sulfonic acid, and further using zinc chloride, cadmium chloride, tin chloride, etc. The diazonium salt can also be stabilized by forming a complex compound.

In the present invention, a multicolor recording material can be obtained by using diazo compounds having different photodecomposition wavelengths or different photodecomposition rates.

[0019] The microcapsules used in the present invention are
After emulsifying and dispersing a solution of a diazonium salt and the same or different compounds that react with each other to produce a polymeric substance in a non-aqueous solvent having a boiling point of 40 to 95°C at normal pressure in a hydrophilic protective colloid solution, While reducing the pressure in the reaction vessel, the temperature of the system is raised to distill off the solvent and move the wall-forming substance to the surface of the oil droplet, and the polymer production reaction by polyaddition and polycondensation proceeds on the surface of the oil droplet to form a wall film. From the viewpoint of obtaining a good shelf life, it is preferable to use microcapsules produced by forming a substantially solvent-free microcapsule. Further, in the present invention, the polymeric substance forming the wall of the microcapsule is preferably formed of at least one selected from polyurethane and polyurea.

[0020] The nonaqueous solvent for dissolving the diazonium salt used in the present invention includes halogenated hydrocarbons,
Preferably, it is at least one compound selected from fatty acid esters, ketones, and ethers.

The same or different compounds which react with each other to produce a polymeric substance and which form the walls of the microcapsules used in the present invention are preferably polyurea or urethane, and the corresponding monomers are aromatic or aliphatic isocyanate compounds. selected. The microcapsules containing the diazo compound of the present invention can be polymerized with the corresponding monomer, and the amount of monomer used is such that the average particle size of the microcapsules is 0.3μ to 12μ, the wall thickness is 0.
．． It is determined to be between 01 and 0.3. Further, it is preferable to apply the diazo compound at a rate of 0.05 to 5.0 g/m2.

[0022] In the present invention, coupling components that can be used together with the coupling component represented by general formula (1) for the purpose of hue adjustment, etc., include those that form a dye by coupling with a diazo compound in a basic atmosphere. Any compound is possible. For example, there are so-called active methylene compounds having a methylene group next to a carbonyl group, phenol derivatives, naphthol derivatives, etc. Specific examples include the following, which are used within the range that meets the purpose of the present invention. Resorcin, phloroglucin, sodium 2,3-dihydroxynaphthalene-6-sulfonate, 1-hydroxy-2-naphthoic acid morpholinopropylamide, 1,5-
Dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,3-dihydroxy-6-sulfanylnaphthalene, 2-hydroxy-3-naphthoic acid morpholinopropylamide, 2-hydroxy-3-naphthoic acid octylamide, 2-hydroxy-3- naphthoic acid anilide, benzoylacetonilide, 1-phenyl-3-methyl-5
-pyrazolone, 1-(2,4,6-trichlorophenyl)-3-anilino-5-pyrazolone, 2-[3-α-(
2,5-di-tert-amylphenoxy)-butanamidobenzamide]phenol, 2,4-bis-(benzoylacetamino)toluene, 1,3-bis-(pivaloylacetaminomethyl)benzene

In the present invention, an organic base is added for the purpose of making the system basic during thermal development and promoting the coupling reaction. These organic bases can be used alone or in combination of two or more. Basic substances include tertiary amines, piperidines,
Examples include nitrogen-containing compounds such as piperazines, amidines, formamidines, pyridines, guanidines, and morpholines. In particular, N,N'-bis(3-phenoxy-2-hydroxypropyl)piperazine, N,N'
-bis[3-(p-methylphenoxy)-2-hydroxypropyl]piperazine, N,N' -bis[3-(p
-methoxyphenoxy)-2-hydroxypropyl]piperazine, N,N' -bis(3-phenylthio-2-
hydroxypropyl)piperazine, N,N'-bis[
3-(βnaphthoxy)-2-hydroxypropyl]piperazine, N-3-(βnaphthoxy)-2-hydroxypropyl-N'-methylpiperazine, 1,4-bis{[3-(N-methylpiperazino)-2 -Hydroxy]
piperazines such as propyloxy}benzene, N-[
3-(βnaphthoxy)-2-hydroxy]propylmorpholine, 1,4-bis[(3-morpholino-2-
Morpholines such as hydroxy)propyloxy]benzene, 1,3-bis[(3-morpholino-2-hydroxy)propyloxy]benzene, N-(3-phenoxy-2-hydroxypropyl)piperidine, N-dodecylpiperidine, etc. Specifically, guanidines such as piperidines, triphenylguanidine, tricyclohexylguanidine, and dicyclohexyl phenylguanidine are preferable. In the present invention, it is preferable to use the coupling component in an amount of 0.1 to 30 parts by weight and the basic substance in an amount of 0.1 to 30 parts by weight per 1 part by weight of the diazo compound.

In the present invention, in addition to the organic base, a coloring aid may be added for the purpose of promoting the coloring reaction. The coloring aids of the present invention include, for example, phenol derivatives, naphthol derivatives,
Alkoxy-substituted benzenes, alkoxy-substituted naphthalenes, hydroxy compounds, amide compounds, and sulfonamide compounds can be added. These compounds are thought to lower the melting point of the coupling component or the basic substance, or to improve the thermal permeability of the microcapsule wall, resulting in a high color density. The coloring aids of the present invention also include thermofusible substances. The heat-melting substance is a substance having a melting point of 50°C to 150°C that is solid at room temperature and melts by heating, and is a substance that dissolves a diazo compound, a coupling component, or a basic substance. Specific examples of these compounds include fatty acid amides, N-substituted fatty acid amides, ketone compounds, urea compounds, esters, and the like.

[0025] The coupling component used in the present invention is:
Although it can be used as a solid dispersion together with a water-soluble polymer using a sand mill or the like together with a basic substance, other coloring aids, etc., it is particularly suitable for use in the form of an emulsion together with a suitable emulsifying aid. Preferred water-soluble polymers include water-soluble polymers used when preparing microcapsules (for example, JP-A-59-19
(See No. 0886). In this case, the coupling component, basic substance, and coloring aid are each added in an amount of 5 to 40% by weight based on the water-soluble polymer solution. Preferably, the dispersed or emulsified particle size is 10 microns or less.

A free radical generator (a compound that generates free radicals when irradiated with light) used in photopolymerizable compositions is added to the recording material of the present invention for the purpose of reducing yellowing of the background after copying. be able to. Examples of the free radical generator include aromatic ketones, quinones, benzoin, benzoin ethers, azo compounds, organic disulfides, and acyloxime esters. The amount of free radical generator to be added is 0.01 to 5 parts by weight of the diazo compound.
Parts by weight are preferred. Similarly, for the purpose of reducing yellowing, a polymerizable compound having an ethylenically unsaturated bond (hereinafter referred to as a vinyl monomer) can be used. A vinyl monomer is a compound having at least one ethylenically unsaturated bond (vinyl group, vinylidene group, etc.) in its chemical structure, and has the chemical form of a monomer or prepolymer. Examples thereof include unsaturated carboxylic acids and salts thereof, esters of unsaturated carboxylic acids and aliphatic polyhydric alcohols, amides of unsaturated carboxylic acids and aliphatic polyhydric amine compounds, and the like. The vinyl monomer is used in an amount of 0.2 to 20 parts by weight per 1 part by weight of the diazo compound. The free radical generator and vinyl monomer are
It can also be used by being contained in microcapsules together with a diazo compound.

In the present invention, in addition to the above-mentioned materials, acid stabilizers such as citric acid, tartaric acid, oxalic acid, boric acid, phosphoric acid, and pyrophosphoric acid can be added.

The recording material of the present invention is produced by preparing a coating solution containing microcapsules containing a diazo compound, a coupling component, an organic base, and other additives, and coating the solution on a support such as paper or a synthetic resin film. Apply by coating methods such as bar coating, blade coating, air knife coating, gravure coating, roll coating, spray coating, dip coating, curtain coating, etc., and dry to a solid content of 2.5 to 30 g/m.
2 photosensitive layers are provided. In the recording material of the present invention,
The microcapsules, the coupling component, the base, etc. may be contained in the same layer as described in the above method, or a laminated structure in which they are contained in separate layers may be adopted. It is also possible to provide an intermediate layer on the support as described in Japanese Patent Application No. 177,669/1980, and then coat the photosensitive layer.

As the support of the present invention, any paper support used for ordinary pressure-sensitive paper, thermal paper, dry or wet diazo copying paper, etc. can be used, as well as neutral paper supports such as alkyl ketene dimer. Neutral paper with a pH of 5 to 9 sized with a sizing agent (described in Japanese Patent Application No. 14281/1982), which satisfies the relationship between Steckigt sizing degree and metric basis weight described in Japanese Patent Application Laid-Open No. 116687/1982, and Paper with a Bekk smoothness of 90 seconds or more, an optical surface roughness of 8 μ or less and a thickness of 30 μm or less as described in JP-A-58-136492.
150μ paper, density 0 as described in JP-A-58-69091
．． 9g/cm3 or less and an optical contact ratio of 15% or more, made from pulp beaten to 400cc or more with Canadian standard freeness (JIS P8121) described in JP-A No. 58-69097. A paper that prevents staining, a base paper made by a Yankee machine described in JP-A No. 58-65695, whose glossy side is used as the coated surface to improve color density and resolution, and a base paper described in JP-A-59-35985. It is also possible to use paper that has been subjected to corona discharge treatment to improve coating suitability. Further, the synthetic resin film used as a support in the present invention can be arbitrarily selected from known materials that do not deform even when heated during the development process and have dimensional stability. Examples of such films include polyester films such as polyethylene terephthalate and polybutylene terephthalate, cellulose derivative films such as cellulose triacetate films, polystyrene films, polypropylene films, and polyolefin films such as polyethylene. It can be used as The thickness of the support used is 20 to 200 microns.

When forming an image on the recording material of the present invention,
The following method can be used. One method is to expose a document to light to form a latent image, and then irradiate light onto areas other than the image forming area to fix the image.
This is a method of obtaining a colored image using heat from a thermal pen, thermal head, etc., and then fixing the image by irradiating light onto areas other than the image area. Either method can be preferably used. As light sources for exposure, various fluorescent lamps, xenon lamps,
It is preferable that a mercury lamp or the like be used, and that the emission spectrum of the lamp substantially matches the absorption spectrum of the diazo compound used in the recording material, since areas other than the image forming area can be efficiently fixed by light. Further, in the step of heating and developing the material, a thermal pen, a thermal head, an infrared ray, a high frequency, a heat block, a heat roller, etc. can be used as the heating means. EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.

[0031]

【Example】

Example 1 [Preparation of capsule liquid A of the present invention]: 1-morpholino-2
, 3.45 parts of 5-dibutoxybenzene-4-diazonium hexafluorophosphate and 18 parts of an adduct of xylylene diisocyanate and trimethylolpropane (3:1) were added to 10 parts of ethyl acetate and dissolved by heating. This diazo compound solution was mixed with an aqueous solution containing 5.2 parts of polyvinyl alcohol dissolved in 58 parts of water, and emulsified and dispersed at 20°C to obtain an emulsion having an average particle size of 2.5 μm. 100 parts of water was added to the obtained emulsion and heated to 50° C. while stirring, and after 3 hours, a capsule liquid containing a diazo compound in the core substance was obtained.

[Preparation of coupler/base emulsion B]: 10 parts of 2-(2-dodecyloxyphenyl)-1,3-dioxane-4,6-dione, which is a specific compound of the present invention, and 5 parts of triphenylguanidine. 3 parts of tricresyl phosphate were dissolved in 50 parts of ethyl acetate, added to 200 parts of a 15% polyvinyl alcohol aqueous solution, and emulsified and dispersed using a homogenizer. This was kept at 30°C to remove ethyl acetate to obtain emulsion B. The average particle size of the emulsion was 0.5μ.

[Preparation of recording material of the present invention]: 50 parts of emulsion liquid B was added to 50 parts of the above capsule liquid A to prepare a coating liquid. This coating solution was applied to a smooth and transparent polyethylene terephthalate film (thickness 75 μm) using a coating bar to give a dry weight of 10 g/m2.
The recording material was prepared by drying for a minute.

[Test of color development and fixation] A test original (a circle of 3 cm diameter painted uniformly black on tracing paper with a 2B pencil) was placed on top of the above recording material and exposed to light using a fluorescent lamp. At this time, a fluorescent lamp whose emission spectrum has a maximum value at 420 nm was used. Next, an image was formed by heating for 3 seconds using a heat block heated to 120°C. The formed image was colored red. Further, even when the entire surface was exposed to light using a lamp having an absorption maximum at 420 nm after heating with a heat block previously heated to 120 DEG C., the formed image developed a reddish color. When the density of the colored portion was measured using a Macbeth densitometer, it was 1.25.

Example 2 2-(2-dodecyloxyphenyl) used in Example 1
-1,3-dioxane-4,6-dione instead of 2
-(2-decyloxyphenyl)-1,3-dioxane-4,6-dione was used to obtain a coupler/base emulsion, but the same procedure as in Example 1 was carried out to prepare a recording material and image. was formed. The formed image was colored red, and when the density of the colored part was measured with a Macbeth densitometer, it was 1.22.
Met.

Example 3 2-(2-dodecyloxyphenyl) used in Example 1
-1,3-dioxane-4,6-dione instead of 2
-methyl-2-(2-octyloxyphenyl)-1,
A recording material was prepared and an image was formed in the same manner as in Example 1 except that 3-dioxane-4,6-dione was used to obtain a coupler/base emulsion. The formed image developed a reddish color, and the density of the colored area was measured using a Macbeth densitometer and found to be 1.21.

Comparative Example 1 2-(2-dodecyloxyphenyl) used in Example 1
-1,3-dioxane-4,6-dione instead of 5
, 5-dimethyl-1,3-cyclohexanedione (Comparative Example 1) to obtain a coupler/base emulsion, but the same operations as in Example 1 were carried out to form an image. The formed image developed a reddish color, and when the density of the colored portion was measured using a Macbeth densitometer, it was 1.20.

Comparative Example 2 2-(2-dodecyloxyphenyl) used in Example 1
-1,3-dioxane-4,6-dione instead of 5
An image was formed in the same manner as in Example 1, except that -phenyl-4-methoxycarbonyl-1,3-cyclohexanedione was used to obtain a coupler/base emulsion. The formed images developed a reddish color, and the density of the colored areas was measured using a Macbeth densitometer and was found to be 1.19.

Next, the storage stability and fogging of the background portion of the obtained recording materials were compared. Storage test: 40℃, 90%
This was done by observing the transparency of the material left for one day under RH conditions. If the storage stability is poor, the material will appear cloudy and will not be suitable as a recording material. Further, a test for fogging on the background part was conducted by measuring the density of the background part using a Macbeth densitometer. The results are shown in Table 1.

[0040]

[Table 1]

These results show that the coupling component of the present invention is excellent in emulsion storage stability, stability, and prevention of fogging on the skin.

Claims (4)

[Claims] 1. A light and heat sensitive recording material comprising a recording layer containing a diazo compound, a coupling component, and an organic base provided on a support, characterized in that the coupling component is a cyclic ester derivative of malonic acid. A light- and heat-sensitive recording material. 2. The light and heat sensitive recording material according to claim 1, wherein the cyclic ester derivative of malonic acid is a 1,3-dioxane-4,6-dione derivative. 3. The light and heat sensitive recording material according to claim 1, wherein the 2-position of the 1,3-dioxane-4,6-dione derivative is substituted. 4. The light and heat sensitive recording material according to claim 1, wherein the diazo compound is contained in microcapsules.