JPH0465291A - Photosensitive thermal recording material - Google Patents

Abstract

PURPOSE:To enhance the uniformity of a color forming layer by specifying a coupling component enhanced in oil solubility. CONSTITUTION:In a photosensitive thermal recording material wherein a recording layer containing a diazo compound, a coupling component and an org. base is provided on a support, the coupling component being a 15C or more cyclohexane-1, 3-dione derivative substituted with an alkyl or aryl group containing a nitrogen atom at its fifth position is used to make it possible to obtain the photosensitive thermal recording material excellent in the preservability and stability of an emulsion and low in the fog of a background part. As the cyclohexane-a, 3-dione derivative, one whose fourth position is substituted with an electron withdrawing group such as a substituted carbonyl group or a cyano group or a hydrogen group is pref. from an aspect easy to synthesize and easy to obtain a raw material.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Field of Application> The present invention relates to a recording material that utilizes the photosensitivity of a diazo compound (diazonium salt), and particularly to a red coloring type light and heat sensitive recording material.

<Prior Art> There are three types of recording materials that utilize the photosensitivity of diazo compounds.

The first 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 developed in an alkaline solution. It is something to do. 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 by heating in the photosensitive layer, and a type that contains trichloroacetic acid in the photosensitive layer. Type containing alkaline salts of acids that lose their acidic properties when heated, such as higher fatty acids 7
There is a type that uses mido as a coloring aid and activates the diazo compound and coupling component by heating and melting.

In addition to maintenance problems such as the need for replenishing and discarding the liquid because the wet type uses a developing solution and the large size of the device, the wet type also has problems with maintenance, such as the fact that it is wet immediately after copying, making it difficult to make additions immediately. , there are several problems such as copy images not being able to withstand long-term storage. In addition, like the wet type, the dry type requires replenishment of developer, requires gas absorption equipment to prevent the generated ammonia gas from leaking outside, and therefore requires larger equipment. ``There are problems such as the smell of ammonia immediately after copying. On the other hand, unlike the wet and dry types, the thermal development type has the advantage of maintenance because it does not require a developing solution. Moreover, if the temperature is not controlled to about ±10<6>C, insufficient development may occur or the color tone may change, resulting in a problem of increased 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 to 130°C)
Although many attempts have been made to improve the temperature of the material (°C), they have 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, each component instantly melts, diffuses, and reacts with the coloring dye. It is necessary to generate , but it is preferable to make the system basic during this reaction because it 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.

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 several attempts have been made to create light and heat sensitive recording materials with good shelf life and high recording speeds, the current situation is that they have not yet reached the point where they can be put to practical use. be.

If you 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. In particular, in the case of a red coloring type recording material, there is a problem in that even slight coloring (fogging) of the background becomes noticeable due to high visibility. In order to solve this incompatible problem, the inventors of the present invention made extensive studies and found that a photosensitive layer that can be thermally developed and contains a diazo compound, a force/sampling component, and a basic substance is provided on a support. Concerning materials, we continued to investigate ways to incorporate the diazo compound into microcapsules, as well as searching for basic substances and how to make microcapsules, and succeeded in suppressing skin discoloration during storage before copying. . (Unexamined Japanese Patent Publication No. 2-542
5'1) However, it was found that 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. Therefore, it became necessary to develop a cyclohexane-1,3-dione derivative with improved dispersion stability. Therefore, a first 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.

<Means for Solving the Problems> The above-mentioned aspects of the present invention provide 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. Ring component is 5
This was achieved using a photosensitive and thermosensitive recording material characterized by being a cyclohexane-1,3-dione derivative having a total carbon number of 15 or more and substituted with an alkyl group or an aryl group containing a nitrogen atom in the position.

Among the cyclohexane-1,3-dione derivatives according to the present invention, from the viewpoint of ease of synthesis and availability of raw materials, 4
Those in which the -position is substituted with an electron-withdrawing group such as a substituted carbonyl group or a cyano group, or a hydrogen atom are preferred.

Among the cyclohexane-1,3-dione derivatives having a total carbon number of 15 or more and substituted with an alkyl group or an aryl group containing a nitrogen atom at the 5-position according to the present invention, the following general formula [1]
Compounds represented by are preferred.

group, cyano group, alkylcarbonyl group, arylcarbonyl group, others may be the same or different and hydrogen atom,
It represents an alkyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group, a cyano group, an alkylcarbonyl group, or an arylcarbonyl group, and R5 and R6 represent a nitrogen atom-containing furkyl group or an aryl group. ) In general formula [1], at least one of the groups represented by RI, R2R3 and R4 is preferably a hydrogen atom, an alkoxycarbonyl group having 2 to 25 carbon atoms, or a cyano group, particularly a hydrogen atom or a carbon atom. An alkoxycarbonyl group having a number of 2 to 20 and a cyano group are preferred. The others are hydrogen atoms,
An alkyl group having 1 to 8 carbon atoms is preferred, and a hydrogen atom and an alkyl group having 1 to 4 carbon atoms are particularly preferred.

(In the above formula, at least one of R', R2, R3 and R4 is a hydrogen atom, alkoxycarbonyl general formula [1]
Among the °alkyl groups or aryl groups represented by R5 and Rs, those having a partial skeleton represented by the general formula [11] are preferred.

(In the above formula, R7, RI Rf , RIOR1+ and RI2 may be open or different and represent a hydrogen atom, an alkyl group or an aryl group.) The partial skeleton represented by the general formula [11] is directly an alkyl group. or an aryl group, or may be bonded to an alkyl group or an aryl group via a divalent group.

In general formula [11], R', RI, R', R10,
The groups represented by R11 and R12 may further have a substituent, and examples of the substituent include an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a substituted amino group,
Examples include substituted carbonyl groups and halogen atoms.

The number of carbon atoms in RS Rs varies depending on the number of carbon atoms in cyclohexane-1, °3-dione, which is 6, and the number of carbon atoms in RI R2, R3, and R4, but is generally 15.
Any number that is greater than or equal to the above may be used.

While satisfying such conditions, RS R@ is a dialkylaminoalkyl group having 3 to 30 carbon atoms, a 7-sylaminoalkyl group having 3 to 30 carbon atoms, and 8 carbon atoms.
~4o 7-sylaminophenyl group, number of carbon atoms 9-50
acylaminoalkylphenyl group, having 9 to 5 carbon atoms
o is preferably an acylaminoalkyloxyphenyl group, a dialkylaminoalkyloxyphenyl group having 9 to 5° carbon atoms, or a di(acylaminoalkyloxy)phenyl group having 18 to 70 carbon atoms. (However, here, acyl includes aromatic-containing groups such as benzoyl.) Next, specific examples of the coupling component according to the present invention are shown below, but the present invention is not limited thereto. .

Examples include.

(II) The cyazo 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. Photodegradable compounds are used that decompose when exposed to light.

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. Also, the maximum absorption wavelength of diazo compounds ranges from around 200 nm to 70 nm, depending on their chemical structure.
It is known that it changes to about 0 nm. (“Photodecomposition and chemical structure of photosensitive diazonium salts” by Takahiro Tsunoda and Ao 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 is decomposed by light of a specific wavelength depending on its chemical structure. Furthermore, by changing the chemical structure of the diazo compound, the hue of the dye after the reaction can be changed even when the same coupling component is used for the coupling reaction.

A diazo compound is a compound represented by the general formula ArN2X. (In the formula, Ar represents a substituted or unsubstituted aromatic ring, and N
2 represents a diazonium group, and X represents an acid anion. ) In the present invention, a multicolor recording material can be obtained by using diazo compounds having different photodecomposition wavelengths or different photodecomposition rates. Specific examples of the diazo compound used in the present invention include the following examples.

4-Diazo-1-dimethylaminobenzene, 4-diazo-2-butoxy-5-chloro-1-dimethylaminobenzene, 4-diazo-1-methylbenzylaminobenzene 4-diazo-1-ethylhuman 0xyethylaminobenzene, 4-diazo-1-diethylamino-3-methoxybenzene, 4-diazo-1-morpholinobenzene, 4-diazo-1-morpholino-2,5-dibutoxybenzene,
4-Diazo-1-tolylmercapto-2,5-jethoxybenzene, 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-7milfezoxyα-butanoylpiperidino)benzene, 4-diazo-1-(4-
methoxy)phenylthio-2,5-jethoxybenzene, 4-diazo-1-(4-methoxy)benzamide-2
,5-jethoxybenzene.

4-Diazo-1-pyrrolidino-2-methoxybenzene Specific examples of the acid that forms a diazonium salt with the above diazo compound include the following examples.

C, F2. , +1COOH (n is an integer from 1 to 9), C1
F t-++ S O3H (m is an integer of 1 to 9), boron tetrafluoride, tetraphenylboron, hexafluorophosphoric acid, aromatic carboxylic acid, aromatic sulfonic acid °.

Furthermore, the diazonium salt can be stabilized by forming a complex compound using zinc chloride, cadmium chloride, tin chloride, or the like.

The microcapsules used in the present invention have a
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 with a boiling point of 95°C in a hydrophilic protective colloid solution, the reaction vessel is reduced in pressure. By increasing the temperature of the system while distilling off the solvent, the wall-forming substance is transferred to the oil droplet surface, and a polymer production reaction by polyaddition and polycondensation proceeds on the oil droplet surface to form a wall film. Preferably, the microcapsules produced are substantially solvent-free from the viewpoint of obtaining a good shelf life.

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.

The non-aqueous solvent in which the diazonium salt used in the present invention is dissolved is at least one selected from halogenated hydrocarbons, fatty acid esters, ketones, and ethers.
Preferably, it is a species compound.

Specific examples of the nonaqueous solvent used in the present invention are listed below, but the present invention is not limited thereto. (
) indicates the boiling point at normal pressure.

Acetone (56), Isoamyl methyl ether (9)
1), isopropyl methyl ketone (94).

Methyl isobutyrate (92), ethyl isobutyl ether J
9) ethyl isopropylene 54)
, ethylpropyl ether (64).

t-7mil chloride (86), ethylene chloride (84).

Isobutyl chloride (69), butyl chloride (7B).

Ethylidene chloride (57), propyl chloride (46).

Methylene chloride (42), ethyl formate (54).

Propyl formate (81), chloromethyl methyl ether (
59), methyl chloroformate (71), ethyl acetate (
77), methyl acetate (57), tetracarbon (77)
, 1.1-zigolpropane (86).

Trichlorethylene (87), methyl propionate (
a O), propyl ether (91), methyl chloride
oform (74), chloroform (61) The microcapsules of the present invention are characterized in that they do not substantially contain non-aqueous solvents. We have developed a method for quantifying the amount of non-aqueous solvents contained in the liquid by the following method, and defined the term "substantially free" in the present invention.

The microcapsules of the present invention are rarely used as a capsule liquid alone, but are generally used by preparing a coating liquid with a coupler or a base, applying it, drying it, and making it exist in a film of a copying material. be. Therefore, the amount of non-aqueous solvent contained in the coating film, which was present at several percent in the capsule liquid stage, was below the detection limit. ; Microcapsule liquid produced by the production method of the present invention 0.
19 was weighed into a 20 cc volumetric flask, methanol was added to make exactly 20 cc, and the volume was left for 30 minutes. 2 cc of the above methanol solution was measured using a microsyringe and injected into a gas chromatograph mass spectrometer (Hitachi M-80B). Column is DENAX 3mm
φX1m was used. Quantification was performed using m/z peaks depending on the solvent to be measured. (For example, in the case of ethyl acetate, m
/z=43. For methylene chloride, peak 84 was used. ) According to this measurement method, the microcapsule liquid of the present invention contains l.
to, 01-3.00% non-aqueous solvent was included.

The same or different compounds that react with each other to produce a polymer substance forming the walls of the microcapsules used in the present invention are preferably polyurea or urethane, and the corresponding monomers are selected from aromatic or aliphatic incyanate compounds. Ru. The microcapsules containing the diazo compound of the present invention can be polymerized with a corresponding monomer, and the amount of monomer used is such that the average particle size of the microcapsules is 0.3 μm to 12 μm, and the wall thickness is 0.3 μm. O'1
It is determined to be ~0.3. Moreover, it is preferable to apply the diazo compound at 0.05 to 5.09/m'.

In the present invention, the force/sampling component that can be used for the purpose of hue adjustment, etc. together with the coupling component represented by general formula [1] is one that forms 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, FuOoglucine, Sodium 2,3-dihydroxynaphthalene-6-sulfonate, 1-HumanOxy-2-naphthoic acid molyborinopropylamide, 1.5-
Dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,3-dihydroxy-6-sulf7ylnaphthalene, 2-hydroxy-3-naphthoic acid morpholopyramide, 2-human 0x-3-naphthoic acid octyl 7mide, 2 -hydroxy-3-naphthoic acid 7nylide,
Pencylacetonilide, 1-phenyl-3-methyl-
5-pyrazolone, 1- (2,4,6-tricOOphenyl)-3-7nilino 5-pyrazolone, 2- (3-
a-(2,5-di-tert-7milphenoxine~
Butane 7midobenz7midophenol, 2,4-bis-(benzoylacetamino)toluene, 1,3-bis-(bivalylacetaminomethyl)benzene In the present invention, the system is made basic during thermal development. An organic base is added to promote 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-hydroxybrobyl)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-(β-naphthoxy)-2-hydroxypropyl]piperazine, N
-3(β-naphthoxy)゛-2-hydroxypropyl-N'-methylpiperazine, 1,4-bis([3(N-methylpiperazino)-2-hydroxy]propyloxy)
Piperazines such as benzene, N-[3-(β-naphthoxy)-2-hydroxy]propylmorpholine, 1.4
-bis[(3-morpholino-2-hydroxy)propyloxy]benzene, 1,3-bis[(3-morpholino-
Morpholines such as 2-hydroxy)propyloxy]benzene, piperidines such as N-(3-phenoxy-2-hydroxypropyl)piperidine and N-dodecylpiperidine, triphenylguanidine, tricyclohexylguanidine, dicyclohexylphenylguanidine, etc. Specifically preferred are guanidines and the like.

In the present invention, the coupling component is 0.1 to 3 parts by weight and the basic substance is 0 parts by weight per 1 part by weight of the diazo compound.
It is preferable to use it in a proportion of 1 to 30 parts by weight.

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, and hydroxy compounds in the photosensitive layer so that thermal development can be carried out quickly and completely with low energy. , amide compounds, and sulfonamide compounds can be added. It is thought that these compounds lower the melting point of the coupling component or the basic substance, or improve the heat 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.

The coupling component used in the present invention includes a basic substance,
It can also be used as a solid dispersion with a water-soluble polymer using a sand mill etc. together with other color development aids, etc.
It is particularly suitable for use in emulsions with appropriate emulsification aids.

Preferred water-soluble polymers include water-soluble polymers used when preparing microcapsules (see, for example, JP-A-59-190886). In this case, the coupling component, the basic substance and the coloring aid are each added in an amount of 5 to 40% by weight based on the water-soluble polymer solution. The dispersed or emulsified particle size is preferably 10 microns or less.

A free radical generator (a compound that generates free radicals when irradiated with light) used in photopolymerizable compositions can be added to the recording material of the present invention for the purpose of reducing yellowing of the background after copying. . As free radical generators, aromatic ketones,
Examples include quinones, benzoin, benzoin ethers, azo compounds, organic disulfides, and 7-syloxime esters. The amount of the free radical generator to be added is preferably 0.01 to 5 parts by weight per 1 part by weight of the diazo compound.

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.

Vinyl monomers have at least one ethylenically unsaturated bond (vinyl group, vinylidene group, etc.) in their chemical structure.
It is a compound that has the chemical form of a monomer or a 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 the vinyl monomer can also be used while being contained in microcapsules together with the diazo compound.

In the present invention, in addition to the above materials, citric acid is used as an acid stabilizer.
Tartaric acid, oxalic acid, boric acid, phosphoric acid, pyrophosphoric acid, etc. 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 it on a support such as paper or a synthetic resin film with a bar. A photosensitive layer with a batch weight of 2.5 to 30 g/m<2> is provided by coating and drying by a coating method such as , blade coating, air knife coating, gravure coating, roll coating, spray coating, dip coating, or curtain coating. The recording material of the present invention may have a laminated structure in which the microcapsules, coupling components, bases, etc. may be contained in the same layer as described in the above method, or may be contained in separate layers. You can also do it. 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, and in addition, neutral sizing agents such as alkyl ketene dimers can be used. Sized neutral paper with a pH of 5 to 9 (described in Japanese Patent Application No. 14281/1983), which satisfies the relationship between Steckigt sizing degree and metric basis weight as described in Japanese Patent Application Laid-open No. 116687/1982, and has Bekk smoothness. 90 seconds or more paper, paper with an optical surface roughness of 8μ or less and a thickness of 30 to 150μ as described in JP-A-58-136492, density 0.9g/ as described in JP-A-58-69091 c.
m' or less and has an optical contact ratio of 15% or more, Canadian standard freeness (JIS) described in JP-A-58-69097.
Paper made from pulp beaten to 400 cc or more with P8121)' to prevent the coating solution from seeping in. The glossy side of the base paper made by the Yankee machine described in JP-A No. 58-65695 is used as the coated surface, and the color density and It is also possible to use paper that improves resolving power, such as paper that has been subjected to corona discharge treatment on the base paper described in JP-A No. 59-35985 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 is 20 to 200
μ is used.

When forming an image on the recording material of the present invention, the following method can be used. One is to expose the original to light to form a latent image, and then irradiate light onto areas other than the image forming area to fix the image.The other is to develop color using heat from a thermal pen, thermal head, etc. In this method, after obtaining an image, the area other than the image area is irradiated with light to fix the image. Either method can be preferably used. Various types of fluorescent lamps, xenon lamps, mercury lamps, etc. are used as light sources for exposure, and the fact that the emission spectrum almost matches the absorption spectrum of the diazo compound used in the recording material is a major factor in light sources other than image formation and part formation. This is preferable because it allows efficient optical fixation. 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.

Example 1 [Preparation of capsule liquid A of the present invention] ~1-morpholino-
3.45 parts of 2,5-dibutoxybenzene-4-diazonium hexafluorophosphate and xylylene diisocyanate and trimethylolpropane (3:1) adduct 1
8 parts 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. This reactor was heated to 400 mA using a water pump.
A vacuum of 9 mmHg to 500 mmHg was maintained. The amount of ethyl acetate in the capsule liquid was determined using the measurement method described above.
A value of 62% was obtained.

[Preparation of coupler/base emulsion B]: 10 parts of the specific compound (11) of the present invention, 5 parts of triphenylguanidine,
Dissolve 3 parts of tricresyl phosphate in 50 parts of ethyl acetate,
It was 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] Second capsule liquid A50
850 parts of the emulsion was added to prepare a coating solution.

This solution was applied to a smooth transparent polyethylene terephthalate film (thickness 75μrr+) using a coating bar to give a dry weight of 10g/m2, and
After drying for 0.1 minute, a recording material was prepared.

[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 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 parts m 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 parts m after heating with a heat block previously heated to 120° C., the formed image developed a reddish color. When the densities of the colored parts were measured using a Macbeth densitometer, they were 1.25 and 1.24, respectively.

Example 2.3 Instead of compound (11) used in Example 1, compound -(
9) (Example 2) and compound (16) (Example 3) were used to obtain a coupler/base emulsion, but the same operations as in Example 1 were performed to prepare a recording material and form an image. . The formed image was colored red, and when the density of the colored part was measured using a Macbeth densitometer, it was 1.22 (Example 2)
, 1.21 (Example 3).

Comparative Example 1.2 Instead of compound (11) used in Example 1, 5.5-
Dimethyl-1,3-cyclohexanedione (Comparative Example 1)
, 5-7cetylaminomethyl-4-methoxycarbonyl-1,3-cyclohexanedione (Comparative Example 2) was used to obtain a coupler/base emulsion. The formed image developed a reddish color, and when the density of the colored area was measured using a Macbeth densitometer, it was 1.20 (Comparative Example 1) and 1.19 (Comparative Example 2), respectively. .

Next, we will discuss the storage stability of the obtained recording material and the fogging of the background part.
compared. The storage stability test was conducted by observing the transparency of the material after it was left at 40° C. and 90% RH for one day. 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 in the background area was conducted by measuring the density of the background area using a Macbeth density needle.

The results are shown in Table 1.

[Table 1] Comparison of storage stability and fog in the background area of recording materials These results show that by using the coupling component of the present invention, the emulsion has excellent storage stability and stability, and has low fog in the background area. A photosensitive and thermosensitive recording material could be obtained.

Claims (1)

[Scope of Claims] 1) 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, wherein the coupling component is an alkyl group containing a nitrogen atom at the 5-position. Total number of carbon atoms substituted with groups or aryl groups: 15
A light and heat sensitive recording material characterized by being the above cyclohexane-1,3-dione derivative. 2) The light and heat sensitive recording material according to claim 1, wherein the diazo compound is contained in microcapsules.