JPH04247448A - Photosensitive heat sensitive recording material - Google Patents

Abstract

PURPOSE:To enhance transparency of a color developing layer and to reduce fog by forming a recording layer containing a diazo compound and a coupling component and an organic base salt on a support and using a 2-cyclohexenone derivative for the coupling component. CONSTITUTION:The 2-cyclohexenone derivative is, preferably, a compound represented by formula I in which each of R1-R3 is H, alkyl, aryl, aralkyl, substituted amino, substituted carbonyl, or cyano group, R4 is substituted carbonyl, cyano groups; and R is alkyl, aryl, substituted carbonyl, substituted sulfonyl, or substituted silyl group.

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 using 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 react. It is necessary to generate coloring pigment using
It is preferable to make the system basic during this reaction since this has the effect of promoting 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.

On the other hand, for light and heat sensitive recording materials, the surface (background) of the recording material becomes colored during storage before copying.
It is also an essential requirement to suppress the decrease in color density as much as possible.

[0006] As described above, it has a good shelf life,
Although the above-mentioned several attempts have been made to create photosensitive and thermosensitive recording materials with high recording speeds, the current situation is that they have not yet reached the point where they can be put to practical use.

[0007] When designing a material that can sufficiently develop color and obtain high density even at low heating temperatures, it is natural that a color reaction may occur even while the material is stored at room temperature before copying. It appears as a phenomenon in which the skin, which should be white, becomes colored. In particular, in the case of red-colored recording materials, slight coloring of the background (fogging) occurs due to high visibility.
But there was a problem with it being noticeable. 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. , we continued to investigate ways to incorporate the diazo compound into microcapsules, search for basic substances, and how to make microcapsules.
We succeeded in suppressing background discoloration during pre-storage. (JP-A-2-54251) However, the coupling component described in the above patent, cyclohexane-1,3-
It was found that dione derivatives actually have low oil solubility and that the storage stability of recording materials after emulsification and dispersion is not very good, necessitating the development of a coupling component that improves the stability of the dispersion.

[0008]

[Problems to be Solved by the Invention] Therefore, the first aspect of the present invention
The object of the present invention is to provide a light and heat sensitive recording material in which the transparency 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.

[0009]

[Means for Solving the Problems] The above objects of the present invention are as follows:
In a light- and heat-sensitive recording material in which a recording layer containing a diazo compound, a coupling component, and an organic base is provided on a support, the coupling component has a 2-substituent at the 6-position.
This was achieved using a light and heat sensitive recording material characterized by being a cyclohexenone derivative.

Among the 2-cyclohexenone derivatives according to the present invention, from the viewpoint of coupling activity with a diazo compound, those having a substituent bonded to the 3-position via a heteroatom such as an oxygen atom, a nitrogen atom, or a sulfur atom are preferred. It is preferable. In particular, it is preferable that the substituent at the 3-position has a substituent bonded via an oxygen atom. Among the 2-cyclohexenone derivatives according to the present invention, those in which the 6-position is substituted with an electron-withdrawing group such as a substituted carbonyl group or a cyano group are preferred from the viewpoint of ease of synthesis and availability of raw materials. .

Among the 2-cyclohexenone derivatives according to the present invention, compounds represented by the following general formula (I) are preferred. The 2-cyclohexenone derivative according to the present invention may contain general formula (II) or (III), which is a tautomer. General formula [I]

0012

[Chemical formula 1]

General formula [II]

[0014]

[Case 2]

General formula [III]

[0016]

[Chemical formula 3]

(In the above formula, R1, R2 and R3 may be the same or different and represent a hydrogen atom, an alkyl group,
represents an aryl group, an aralkyl group, a substituted amino group, a substituted carbonyl group, or a cyano group, R4 is a substituted carbonyl group,
R represents a cyano group, and R represents an alkyl group, an aryl group, a substituted carbonyl group, a substituted sulfonyl group, or a substituted silyl group. ) More preferably, the groups represented by R1, R2 and R3 in general formula (I) include a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 2 carbon atoms. -25 alkoxycarbonyl groups, C2-25 alkylcarbonyl groups, C7-35 arylcarbonyl groups, and cyano groups are preferred. R4 is preferably an alkoxycarbonyl group having 2 to 25 carbon atoms, an alkylcarbonyl group having 2 to 25 carbon atoms, an arylcarbonyl group having 7 to 30 carbon atoms, or a cyano group.

The group represented by R in general formula (I) may have a substituent, and when R is an alkyl group, an aryl group, a substituted carbonyl group, or a substituted sulfonyl group, the substituent is A halogen atom, an alkyl group, an aryl group, an alkoxy group, a substituted carbonyl group, a substituted amino group, and a heterocyclic residue are preferred, and when R is a substituted silyl, an alkyl group,
Aryl groups are preferred. The substituents of these alkyl groups and aryl groups may further have a substituent.

More preferably, R has 1 to 2 carbon atoms.
0 alkyl group, aryl group having 6 to 30 carbon atoms, alkylcarbonyl group having 2 to 20 carbon atoms, arylcarbonyl group having 7 to 20 carbon atoms, 2 to 20 carbon atoms
Preferred are an alkylsulfonyl group having 7 to 20 carbon atoms, an arylsulfonyl group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, and a substituted carbamoyl group having 2 to 20 carbon atoms. Particularly preferred are alkylcarbonyl groups having 2 to 15 carbon atoms, arylcarbonyl groups having 7 to 15 carbon atoms, alkoxycarbonyl groups having 2 to 15 carbon atoms, and substituted carbamoyl groups having 2 to 15 carbon atoms.

Among the 2-cyclohexenone derivatives according to the present invention, for example, when R is a substituted carbonyl group, it can be selectively obtained by esterifying a cyclohexane-1,3-dione derivative. The method of esterification is (
Examples include 1) a method in which a cyclohexane-1,3-dione derivative is reacted with a carboxylic acid halide under basic conditions, and (2) a method in which a cyclohexane-1,3-dione derivative is reacted with a carboxylic acid under acidic conditions. In particular, (1)
The method (formula below) is mild and preferable.

[0021]

[C4]

Next, specific examples of the coupling component according to the present invention are shown below, but the present invention is not limited thereto.

[0023]

[C5]

[0024]

[C6]

[0025]

[C7]

[0026] etc.

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 a 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 (IV). General formula (IV)

[0029]

[Chemical formula 8]

(In the formula, Ar represents a substituted or unsubstituted aromatic ring, 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-ethylhydroxy Ethylaminobenzene, 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-[α-(2,4-di-tert-amylphenoxy)butyrylpiperidino]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 diazo compounds include the following.

Polyfluoroalkylcarboxylic acid having 1 to 9 carbon atoms, polyfluoroalkylsulfonic acid having 1 to 9 carbon atoms, boron tetrafluoride, tetraphenylboron, hexafluorophosphoric acid, aromatic carboxylic acid, aromatic The diazonium salt can also be stabilized by forming a complex using sulfonic acid, and further zinc chloride, cadmium chloride, tin chloride, and the like.

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

[0036] 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 polymer material forming the wall of the microcapsule is preferably formed of at least one selected from polyurethane and polyurea.

[0038] As the non-aqueous solvent for dissolving the diazonium salt used in the present invention, 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.

[0040] In the present invention, coupling components that can be used for the purpose of hue adjustment, etc. together with the coupling component represented by general formula [I] 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-sulfonylnaphthalene, 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-(2,4-di-tert-amylphenoxy)butanamide]benzamide]phenol, 2,4-
Bis-(benzoylacetamino)toluene, 1,3-
Bis-(pivaloylacetaminomethyl)benzene

0
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. Examples of the basic substance include nitrogen-containing compounds such as tertiary amines, piperidines, 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-hydroxy)propyloxy]benzene, 1,3-bis[(
Morpholines such as 3-morpholino-2-hydroxy)propyloxy]benzene, N-(3-phenoxy-2
-hydroxypropyl) piperidine, piperidines such as N-dodecylpiperidine, triphenylguanidine,
Specifically preferred are guanidines such as tricyclohexylguanidine and dicyclohexyl phenylguanidine.

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.

[0047] Included in the color development aid of the present invention are:
For example, phenol derivatives, naphthol derivatives, alkoxy-substituted benzenes, alkoxy-substituted naphthalenes, hydroxy compounds, amide compounds, sulfonamide compounds can be added to the photosensitive layer so that thermal development can be carried out quickly and completely with low energy. . These compounds are
It is thought that the melting point of the coupling component or the basic substance is lowered, or the heat permeability of the microcapsule wall is improved, resulting in a high color density.

[0048] The coloring aids of the present invention also include heat-melting 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.

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.

[0052] The above-mentioned free radical generator and vinyl monomer can also be used by being contained in microcapsules together with the 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 prepared 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.

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. Such films include polyester films such as polyethylene terephthalate and polybutylene terephthalate, cellulose derivative films such as cellulose triacetate film, polystyrene films,
Examples include polypropylene films and polyolefin films such as polyethylene, which can be used alone or in combination. The thickness of the support is
A material having a diameter of 20 to 200 μm is used.

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.

[0058] Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.

Synthesis Example Synthesis Example 1 5-phenyl-4-methoxycarbonyl-cyclohexane-1,3-dione 24.6 g, triethylamine 10
．． Dissolve 6g in 100ml of acetonitrile, cool on ice,
12.5 g of pivaloyl chloride was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred at the same temperature for 1 hour, and the reaction mixture was diluted with 50% water.
It was opened to 0 ml. The precipitated crystals were filtered and recrystallized with alcohol to obtain 29.5 g of compound (8). (Yield=8
9%, m. p. =115~117℃)

Synthesis Example 2 The reaction was carried out in the same manner as in Synthesis Example 1, except that 9.9 g of methyl chloroformate was used instead of pivaloyl chloride, and 27.4 g of compound (9) was obtained. Ta. (Yield = 90%, m.p. = 78-79°C)

006
1] Synthesis Example 3 In Synthesis Example 2, 5-(2-tetradecyloxyphenyl)-4-methoxycarbonyl-1,3 was used instead of 5-phenyl-4-methoxycarbonyl-cyclohexane-1,3-dione. -The reaction was carried out in the same manner as in Synthesis Example 2, except that 45.8 g of dione was used, and compound (15) was obtained.
43.9g was obtained. (Yield=85%, m.p.=63~
64℃)

Synthesis Example 4 In Synthesis Example 2, instead of using 5-phenyl-4-methoxycarbonyl-cyclohexane-1,3-dione, 5-(4-dodecyloxy-3-methoxyphenyl)-4-methoxycarbonyl was used. -1,3-dione 46.0
The reaction was carried out in the same manner as in Synthesis Example 2, except that 44.0 g of compound (26) was obtained. (Yield=85%, m.
p. =79~81℃)

Synthesis Example 5 In Synthesis Example 1, instead of using 5-phenyl-4-methoxycarbonyl-cyclohexane-1,3-dione, 5-(2-decyloxy-1-naphthyl)-4-methoxycarbonyl-1, Synthesis Example 1 except that 45.2 g of 3-dione and 11.3 g of N,N-dimethylcarbamic acid chloride were used instead of pivaloyl chloride.
The reaction was carried out in the same manner as above to obtain 48.6 g of compound (22). (Yield = 93%, m.p. = 79-81°C)

0064
]

[Examples] 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]: Dissolve 10 parts of the specific compound of the present invention (8), 5 parts of triphenylguanidine, and 3 parts of tricresyl phosphate in 50 parts of ethyl acetate, and dissolve 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 Tofu liquid was applied to a smooth 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.

[Color Development and Fixation Test] A test manuscript (a circle with a diameter of 3 cm 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° 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 Compound (1) was used instead of compound (8) used in Example 1.
Example 1 except that the coupler/base emulsion was obtained using 5)
A recording material was prepared and an image was formed by performing the same operation as above. The formed image developed a reddish color, and the density of the colored area was measured using a Macbeth densitometer and found to be 1.22.

Example 3 Compound (2) was used instead of compound (8) used in Example 1.
Example 1 except that the coupler/base emulsion was obtained using 5)
A recording material was prepared and an image was formed by performing the same operations as above. 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 The coupler/base emulsion was obtained by using 5,5-dimethyl-1,3-cyclohexanedione (Comparative Example 1) instead of compound (8) used in Example 1. The same operation as in Example 1 was performed 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 Example 2 except that 5-phenyl-4-methoxycarbonyl-1,3-cyclohexanedione was used instead of compound (8) used in Example 1 to obtain a coupler/base emulsion. The same operation as in 1 was performed to form an image. 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.

[0073]

[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] Claim 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, wherein the coupling component is 2-
A light and heat sensitive recording material characterized by being a cyclohexenone derivative. 2. The light and heat sensitive recording material according to claim 1, wherein the coupling component is a 2-cyclohexenone derivative having a substituent at the 6-position. 3. The light and heat sensitive recording material according to claim 1, wherein the 6-position of the coupling component is substituted with a substituted carbonyl group or a cyano group. 4. The light and heat sensitive recording material according to claim 1, wherein the diazo compound is contained in microcapsules.