JPH01122482A - Recording material - Google Patents

Abstract

PURPOSE:To obtain a recording material satisfactory in color forming properties, shelf stability in raw, coloring image stability, by using a 1-1-bis(4- hydroxyphenyl)butane as an electron accepting compound. CONSTITUTION:1-1-bis(4-hydroxyphenyl)butane can be obtained in such a manner as that; 14g of an n-butylaldehyde is dripped at a temperarure of 30 deg.C or below while 75g of a phenol, 40cc of a concentrated hydrochloric acid catalyst 0.02g of a '-thiopropinonic acid (a reaction accelerator) are stirred, thereafter the stir is continued at 40 deg.C for three hours, the phenol is removed by a steam distillation, and a bisphenol compound is taken out and crystallized by a toluene solvent. As an electron donative colorless dye imparting a coloring material by coming into contact with the electron accepting compound, a leuco compound, a triphenylmethane phthalide compound, a fluorane compound, a triazen com pound, a spiropyrane compound, etc., can be used.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of the Invention) The present invention relates to a recording material, and more particularly to a recording material with improved color development, shelf life, and stability of colored images.

(Prior Art) Recording materials using an electron-donating colorless dye and an electron-accepting compound are already well known as pressure-sensitive paper, thermal paper, light-sensitive pressure-sensitive paper, electrically conductive thermal paper, and the like. For example, British patent
14co, Hiromari issue, US patent≠.

≠to, or-go, Dohiro, Hiro36. ri No. 20, Special Public Sho To-ko 3. Octopus λ, published in Japanese Patent Publication No. 77-/7.

rst issue, 40-/koj, 774, to-12
3.jt! I am familiar with issue 7 etc.

The performance that a recording material should have is (1) sufficient color density and color development sensitivity, (2) no fogging, (3) sufficient fastness of color body, and (4) color development. (5) high S/N ratio, (6) sufficient chemical resistance of the coloring body, etc. In particular, in recent years, the speed of recording systems has increased and demands have increased. With the diversification, research into improving these characteristics is being carried out intensively.

The present inventors investigated the characteristics of each of the electron-donating colorless dye and the electron-accepting compound, including their oil solubility, water solubility, partition coefficient spKas, polarity of substituent, position of substituent, crystallinity and solubility. We have pursued the development of good materials for recording materials and recording materials, focusing on static or dynamic characteristics such as change.

We have discovered that the properties of recording materials can be greatly improved by incorporating unique ideas into electron-accepting compounds. ! As will be described later, the properties of Samurai are significantly improved by using it in combination with a specific amide compound and/or ether compound.

(Objective of the Invention) An object of the present invention is to provide a recording material with good color development, shelf life, and stability of colored images by incorporating a compound in which the raw materials are easily available and the material is easily purified. It is.

(Structure of the invention) The object of the present invention is to provide / as an electron-accepting compound.

This was achieved by developing a recording material using /-bis(μm hydroxyphenyl)methane.

Various synthetic methods can be considered for the compound of the present invention, but in the present invention, it can be easily obtained by dehydration condensation of a phenol and an aldehyde compound in the presence of a catalyst.

The catalyst consists of acid catalysts such as hydrogen chloride and hydrochloric acid.
Further, additives for promoting the reaction include sulfuric acid, calcium chloride, and β-thiopropionic acid.

Phenol is used in a molar ratio of 1 to 10 moles to the aldehyde compound, the reaction temperature is 100C to 700C, and the reaction time is /-20 hours.

A synthesis example is shown below.

(Synthesis example) Zoocc three-mouth 7-glass: Prepare rK phenol 7!2, concentrated hydrochloric acid μOCC, β-thiopropionic acid O, O, and add 3 O”c of butyraldehyde without stirring.
After the dropwise addition, the mixture was stirred at uo'c for 3 hours. Next, after removing phenol by steam distillation, the bisphenol compound was taken out and crystallized with a toluene solvent to obtain crystals.

The melting point of the crystal is 13 ri~tao 0c! DMS(”,
/ea#, z) and NMR analysis /, /-bis(4
cm hydroxyphenyl)butane.

Next, the electron-donating colorless dye that gives a colored product when it comes into contact with the above-mentioned electron-accepting compound will be described.

Examples of electron-donating colorless dyes include the already well-known leuco compounds, triphenylmethane 7-thallide compounds, flufernic compounds, phenothiazine compounds, indolyl phthalide compounds, leuco auramine compounds, and rhodamine. Examples include various compounds such as lactam compounds, triarylmethane compounds, triazene compounds, and spiropyran compounds. - Specific examples of these various existing colorless dyes, such as 7 thallides, can be found in U.S. Reissue Patent No. 1J, No. 02, U.S. Patent No. 3. ≠ri/, No. 111, 3. ≠21.1/No. 3
．． ≠ri/, No. 111, No. 3゜102.77μ, specific examples of fluorans are U.S. Patent J, I, No. 111,107,
Same j, 447.7F7 issue, same J, t4c/, 0// issue,
Same J, $4.2.

r, y: r number, same 3. trt, 3yo issue, same 3. riλo
, Zio, J, 91P, No. 171, and specific examples of spiropyrifs are described in US Patent No. 3. 7/, 10, etc.

Some examples of colorless dyes include triarylmethane compounds such as 3.3-bis(p-dimethylaminophenyl)-6-dimethylaminophthalide and 3.3-bis(p-dimethylaminophthalide).
-diethylaminophenyl)7talido, 3(p-dimethylaminophenyl)-J-(/,j-dimethylindol-3-yl)(aza)7talidos'Cp-dimethylaminophenyl)-J-(J-methyl Indole-3-
yl) 7thalide, etc., as diphenylmethane compounds such as Hiroshi, 1-bis-dimethylaminobenzhydrylbenzyl ether, N-halophenyl-leucoauramine, N-J,≠,j-)lichlorophenylleucoauramine, etc. However, as a xanthine compound, rhodamine-B
-7nilinolactam, rhodamine (p-nitroanilino)lactam, rhodamine l3 (p-chloroanilino)lactam, colabenzylamino-6-diethylaminofluorane, -anilino-6-diethylaminofluorane, -1anilino-3-methyl-6-dietyl Teraminofluorane, 2-7nilino-3-methyl-4-N-cyclohexyl-N-methylaminofluorane, 2-o-chloroanilino-6-diethylaminofluorane, J-m-
) dylamino-3-methyl-6-diethylaminofluorane, 3゜6-dibutoxyfluorane, co-octylclade-6-diethylaminofluorane, colahexadecylamino-6-diethylaminofluorane, λ-m
-) IJ 70 Rometeranilino-6-dimethylaminofluorane, 2-butylamino-3-di.

wax-6-diethylaminofluorane, co-β-phenoxyethoxyethylamino-3-chloro-6-dimethylaminofluorane, co-anilino 3-methyl-6-cyptylamino-t-methylfluoran, lambda-anilino 3-methyl-6-thio Cteramino-j-methylfluorane, co-anilino 3-chloro-6-dinithylaminofluoran, co-anilino 3-methyl-4-N-β-
Pyridylethyl-N-ethylaminofluorane, 2-phenyl-6-dimethylaminofluorane, λ-anilino 3-methyl-AN-ether-N-isoamylaminofluorane, λ-anilino Chloro
6-dietheraminofluorane, noanilino-3-methyl-6-dinithylamino-fumethylfluoran, 2
-anilino-3-7 dinoxy 6-dibutylaminofluorane, 2-p-chloroanilino-3-ethoxy-t-
N-Ether-N-isoamylaminofluorane, No 0
-chloroanilino-6-p-butylanilinofluorane, co-7nilino-3- is phtadecyl-6-diethylaminofluorane, co-anilino-3-ethyl-t-dibu-
thylaminofluorane.

Noanilino-3-methyl-Hiro',! '-dichlorofluoran, J-o-) luidino-3-methyl-4-N-octyl-N-isopropylamino-μ', j'-dimethylaminofluorane, λ-anilino-3-ethyl-J
-N-ethyl-N-isoamylaminofluorane, λ-
Anilino 3-methyl-4-N-ethyl-N-r-2-
Pyridylpropylaminofluor 2-1-anilino 3
-Chloro A-N-ethyl-N-isoamylaminofluorane and the like are 31 examples of fluorene compounds.

t'-bisdiethylamino-y-diethylaminospiro(isobenzo7-l,2'-fluorene)-3-
7M/-bisdimethylamino-dibutylaminospiro(isobenzo7ran-/,P'-fluorene)-3-one, 31.

t'-Bisdibutylamino-yo-diethylaminospiro(isobenzo7-l,ri'-fluorene)-3'-
on, 31.41-bis-N-ethyl-N-inamylaminospiro(inbenzo7-l,ri'-diphenoxyetheramin-!-fluorene)-3-one, etc.
Examples of thiazine compounds include benzoylleucomethylene blue, p-nitro and nzoylleucomethylene blue, and examples of spiro compounds include J-methyl-spiro-dinaphthopyran, 3-ethyl-spiro-dinaphthopyran,
J, J'-dichlorospirozinaphthotheapyran, 3
Examples include -benzylspiro-dinaphthopyran, 3-methyl-naphtho-(3-methoxybenzo)spiropyran, and J-furopyrusspiro-dibenzopyran, and it is desirable to use two or more of them in combination.

In addition to the above-mentioned compounds, examples of electron-accepting compounds that impart color upon contact with colorless dyes include conventionally known compounds, such as phenol visiters, salicylic acid derivatives, metal salts of aromatic carboxylic acids, acid clay, bentonite, and novolak. Resin, metal-treated novolac resin, ≠-tert-butylphenol, Hiro-phenylphenol, λ, cocose (
≠-Hydroxyphenyl)propane, ≠, Hiro'-isopropylidene bis(I2-methylphenol), 'tl-
Bis(3-chloro-hydroxy-7enyl)cyclohexane, 1ll-bis(3-chloro-≠-hydroxyphenyl)-2-ethylbutane, Octylphenol% Hiro.

4"-5ec-butylidene diphenol, Hiro-chlorophenylphenol% da, μ'-isopentylidene diphenol, ≠, 3'-methylcyclohexylidene diphenol, p, l-dihydroxydiphenyl sulfone, l
l≠-bisuhiro'-hydroxycumylbenzene, /, J
-Bisuzhen'-Hydroxycumylbenzene, Hiromu, μ'-
Thiobis(4-1ert-but, thi-3-methylphenol), pl-dihydroxy 3,3'-diallyldiphenylsulfone, hydroquinone monobenzyl ether, ≠-human tetraxybenzophenone, 2. dihydroxybenzophenone, polyvinylbenzyloxycarbonylphenol, 2. Hiroshi, 4I'-trihydroxybenzophenone, J, J', μ.

Hiro'-tetrahydroxybenzophenone, μm dimethyl hydroxyphthalate, methyl dihydroxybenzoate,
J, 4C, l-)lyhydroxydiphenylsulfone, t
, r-bis-p-hydroxybenzoyloxytanthane, l,6-pis-p-hydroxyphenoxyhexane, μ
tolyl m-hydroxybenzoate, h-hydroxybenzoic acid α-7dynylbenzyl ester, di-hydroxybenzoic phenylpropyl, phenethyl 3-chloro-hydroxybenzoate, p-chlorobenzyl dihydroxybenzoate, p-chlorobenzoate -Hydroxybenzoic acid-p-methoxybenzyl, ≠-Hydroxybenzoic acid benzyl ester,
Hydroxybenzoic acid-m-70 lobenzyl ester, hydroxybenzoic acid β-phenethyl ester, ≠-hydroxy-a', e'-dimethyl diphenyl sulfone, β-phenethyl oliseinate, ethyl orselinate, cinnamyl orselinate nate, orselic acid-〇-chlorophenoxyethyl ester, 0-ethelphenoxyethyl orselinate, phenylphenoxyethyl selselinate%m-phenylphenoxyethyl orselinate, λ, hiro-dihydroxybenzoic acid-β-3 '-1-
Butyl-Hiro'-hydroxyphenoxyethyl ester,
/-t-phthyl≠-p-hydro\xyphenylsulfonyloxybenzene, Hiro-N-benzylsulfamoylphenol, co, terdihydroxybenzoic acid-p-) f
Rubenzyl ester, Co, Hiro-dihydroxybenzoic H-
β-phenoxyethyl ester, co,≠-dihydroxy-6-methylbenzoic acid benzyl ester, allyl bis-uderhydroxyphenylacetate, ditolylthiourea, μ′-diacetyldiphenylthiourea, J-phenylsalicylic acid, j p-α- Methylbenzyl-α-methylbenzylsalicylic acid,! -p-methoxyphenoxyethyloxysalicylic acid,! -phenoxyethoxysalitellate, z-p-benzyl-α-methylhenzylsalitellate, 3-xylyl-! −(α.

α-dimethylbenzyl)salicylic acid, 3. ! −G (α
-methylbenzyl)salicylic acid, co-hydroxyl-
Aromatic carboxylic acids such as α-ethylbenzyl-3-naphthoic acid, 3. ! - acids such as dicyclontadienyl salicylic acid or zinc salts, p-hydroxybenzoic aβ-p'
-Methoxyphenoxybuter ester, p-hydroxybenzoic acid δ-phenoxybutyl ester s'+"*'F
p-hydroxybenzoic acid β-p-ethoxyphenoxyethyl ester, p-hydroxybenzoic acid β-phenoxyethoxyethyl ester, p-hydroxybenzoic acid-β
-p-butoxyphenoxyisopropyl ester,
Hiro-dihydroxybenzoic acid -β-p-methoxyphenoxyethoxyethyl ester, orcelic acid phenoxybuter ether, β-resorcinic acid -p-methoxyphenoxyethoxyethyl ether, orcelic acid β-p-methoxyphenoxyethoxyethyl ether, orserif tlEβ
-0-methoxyphenoxyethyl ether, orceric acid tolyloxyethyl ester, orceric acid-β-p
-Methoxyphenoxypropyl ester, β-resorcinic acid phenoxyethyl ether, β-resorcinic acid δ-
p-Methoxyphenoxybuterester, 2-methoxyruboxy! -β-phenoxyethoxyna 7tol, para-7
Organic color developers such as 7 enols such as di-2-2-phenol-formalin resin and /e-rabuterphenol acetylene resin, and combinations of these organic color developers such as zinc, magnesium, aluminum, calcium, titanium, manganese, tin, and nickel. Polyvalent metal salts such as zinc salts, inorganic acids, acid clay, activated clay, athanol guide, bentonite, colloidal silica, aluminum silicate, magnesium silicate, zinc silicate, tin silicate, zinc rhodan, zinc rhodan/benzylantipyrine complexes, inorganic color developers such as zinc chloride, iron stearate, cobalt naphthenate, nickel oxide, ammonium nitrate, carboxylic acids such as succinic acid, maleic acid, tartaric acid, citric acid, succinic acid, stearic acid, benzoylpropionic acid, etc. , benzoic acid, para-tertiary butylbenzoic acid, heptatalic acid, gallic acid, and the like may be used in combination with the electron-accepting compound of the present invention.

When these colorless dyes and electron-accepting compounds are applied to recording materials, they are used in the form of fine dispersions or fine droplets.

When used with pressure sensitive paper, U.S. Patent No. 2,10! , Hiro 7
No. 0, same λ,! 0! , Da 71, same.

101.4Cf No., same, 744F, No. 344, same, 7/, 2. jO7, 7JO, 1Aj6, 2.730, $j7, J10JII044,
Same 3rd. Thank you! Various forms can be used as described in prior patents such as No. θ, 4/LO10OJI, and the like. Most commonly they consist of at least one pair of sheets containing separately an electron-donating colorless dye and an electron-accepting compound.

A method of manufacturing capsules is described in a US patent.

100, 4cJ-7, a method using coacervation of a hydrophilic colloid sol described in J, too, ajt, British Patent RJ7,727, 910,
4c173, same year, 26μ, same year.

Examples include the interfacial polymerization method described in US Pat. No. 0, No. 074, and the method described in US Pat.

In general, electron-donating colorless dyes are used alone or in combination as solvents (alkylated hetathalenes, alkylated diphenyls, alkylated diphenylmethanes, alkylated terphenyls,
Synthetic oils such as chlorinated paraffin; Vegetable oils such as cotton oil and castor oil; Animal oils; Mineral oils and mixtures of these oils, etc.)
After dissolving it in microcapsules,
A color forming agent sheet is obtained by coating it on a transparent or opaque smooth support such as paper, high-quality paper, plastic sheet, resin-coated paper, etc.

Alternatively, an electron-accepting compound, alone or in combination, or together with other electron-accepting compounds, is dispersed in a binder such as sterene-butadiene latex-suborivinyl alcohol, and is used to produce paper, plastic sheets, etc., along with pigments described below.
A developer sheet is obtained by coating a support such as resin-coated paper.

The amounts of the electron-donating colorless dye and the electron-accepting compound to be used depend on the desired coating thickness, the form of the pressure-sensitive copying paper, the capsule manufacturing method, and other conditions, and may be appropriately selected depending on the conditions. It is easy for one skilled in the art to determine this amount to use.

When used in thermal paper, the electron-donating colorless dye and electron-accepting compound have an ioμ or less size in the dispersion medium.

It is preferably used after being pulverized and dispersed to a particle size of 3 μm or less.

As a dispersion medium, a water-soluble polymer aqueous solution having a concentration of about O0λj to IO% is generally used, and the separation is carried out using a ball mill, a sand mill, a horizontal sand mill attritor, a colloid mill, etc.

The ratio of the electron-donating colorless dye to the electron-accepting compound used is from /:10 to /:0. / is preferable,
Furthermore l:! and 2=3 is particularly preferred. At that time, aromatic ether compounds such as JP-A-Sho! If-j
Furthermore, an amide having an aromatic alkyl or substituted alkyl ether and/or a long-chain alkyl group as disclosed in JF-1702 may be used in combination. Examples of such ether compounds are 7enethylbiphenyl, benzyloxynaphthalene, benzylbiphenyl, di-m-
Tolyloxyethane, β-phenoxyethoxyanisole, l-phenoxy-col-ethylphenoxyethane, bis-β-(p-methoxyphenoxy)ethoxymethane, l-λ'-methoxyphenoxycor-ethyloxyphenoxyethane , l,2-diphenoxyethane%'l''-diphenoxybutane, bis-β-(p-ethoxyphenoxy)ethyl ether, l-7 diphenoxyλ
-p-chlorophenoxyethane, /-,2'-methylphenoxyeta"-ethyloxyphenoxyethane,
/-μ′-methylphenoxyλ-p“-fluorophenoxyethane, l-phenoxy-2-p-natoxyphenylthioether, /, J-bis-p-methoxyphenylthioether, l-tolyluo-C-J-p - ethers such as methoxy 7-enylthioether or stearamide, methylene bisstearamide, stearaniside, behenic acid amide, stearanilide,
It is preferable to use a compound such as stearyl urea in combination. These are used in finely dispersed form at the same time as a colorless dye or at the same time as an electron-accepting compound. In particular, it is preferable to disperse the colorless dye at the same time from the viewpoint of preventing fogging. The amount of these to be used is 300% or less by weight relative to the child-accepting compound, and preferably 10% or more and 1jo% or less.

Additives are further added to the coating liquid thus obtained in order to meet various requirements.

Examples of additives include dispersing oil-absorbing substances such as inorganic pigments and polyurea fillers in the binder in order to prevent the recording head from becoming dirty during recording, and also to improve releasability from the head. For this purpose, fatty acids, metal soaps, etc. are added. Therefore, in addition to colorless dyes and electron-accepting compounds that directly contribute to color development, pigments, waxes, antifoaming agents, ultraviolet absorbers, antifoaming agents, conductive agents, fluorescent dyes, surfactants, etc. are generally added. The agent is applied onto the support to constitute the recording material.

Specifically, pigments such as kaolin, calcined kaolin, talc, zinc oxide, diatomaceous earth, calcium carbonate, aluminum hydroxide, calcined carbon, silica, magnesium carbonate, titanium oxide, alumina, barium carbonate, barium sulfate, mica, microphone.

Balloon, urea-formalin filler, polyethylene particles, cellulose filler, etc. particle size 0゜//
Selected from those of jμ.

Examples of waxes include benzyl biphenyl, paraffin wax, carboxy-modified wax, crystalline wax, polyethylene wax, and higher fatty acid esters such as benzyl benzyloxybenzoate and octyl stearate.

Examples of the metal soap include higher fatty acid polyvalent metal salts, ie, zinc stearate, aluminum stearate, calcium stearate, zinc oleate, and the like.

As the hindered phenol, at least
Phenol derivatives in which one or more of the positions are substituted with a branched alkyl group are preferred.

For example, i,i-bis(cometeruderhydroxy-z-t-7'tylphenyl)butane%'1/,j-
) Lis(3-methyl-reference-hydroxy-t-t-butylphenyl)butane, bis(λ-hydroxy-J -t
-butyl-j-methylphenyl)methane, bis(comethyl-≠-hydroxy-!-t-butylphenyl)sulfi)"lE6.

Examples of ultraviolet absorbers include cinnamic acid spinnerets, benzophenone derivatives, benzotriazolylphenol derivatives, etc., such as α-cyano-β-phenylbutyl cinnamate, 0-benzotriazolylphenol, 0-benzotriazolyl-p -chlorophenol, 0-benzotriazolyl-2
, Hiro-dibutylphenol, o-benzotriazolyl p-chlorophenol and the like. Among these, benzotriazole phenol derivatives are particularly preferred.

These materials are also detailed in the patents mentioned above.

These are dispersed and applied in a binder.

Binders are generally water-soluble, such as polyvinyl alcohol, hydroxyethyl cellulose, hydroxypropyl cellulose, epichlorohydrin-modified polyamide, ethylene-maleic anhydride copolymer, styrene-maleic anhydride copolymer, and imbutylene-anhydride. Examples include maleic acid copolymers, polyacrylic acid, polyacrylic acid amide, methylol-modified polyacrylamide, starch derivatives, casein, and gelatin. In addition, water-resistant agents (gelling agents, cross-linking agents) are added to these binders for the purpose of imparting water resistance, emulsions of hydrophobic polymers, specifically styrene-butadiene rubber latex, acrylic resin emulsions, etc. You can also add

Furthermore, for the purpose of imparting chemical resistance to the surface of the coating layer, a gelatinizer consisting of a water-soluble polymer compound such as polyvinyl alcohol, hydroxyethyl starch or epoxy-modified polyacrylamide and a gelling agent (hardening agent) is added. It is also possible to provide layers of approximately λμ.

The coating fluid is most commonly applied onto base paper, wood-free paper or synthetic paper, preferably neutral paper.

Generally, the coating amount is about ko to toy/m2 in terms of solid content.

When used for thermal paper, OLS Co2Jrtri No., OLS Co/101! Da, Tokko Akira! --Various embodiments described in KoO7 Ko2 etc. can be used. Alternatively, operations such as preheating, humidity control, or stretching of coated paper may be added prior to recording.

The electrically conductive thermal paper is manufactured, for example, by the method described in Japanese Patent Application Laid-Open No. 2003-120010/JIIIA, JP-A No. 2003-01-12012, and the like. Generally, a conductive layer is formed by coating a support such as paper with a coating liquid in which a conductive substance, a basic dye mainly composed of fluoran derivatives, and an electron-accepting compound are dispersed together with a binder, or by coating a conductive substance on the support. The electrically conductive thermal paper of the present invention is produced by applying thereon a coating liquid in which a colorless dye, an electron-accepting substance, and a binder are dispersed.

Note that the sensitivity can also be improved by using the thermofusible substance described above in combination.

The photosensitive pressure sensitive paper is manufactured, for example, by the method described in JP-A-77/72134. In general, crosslinking of a photopolymerization initiator such as silver iodobromide, silver bromide, silver behenate, Michler's ketone, henzin derivative, benzophenone derivative, etc. and a polyfunctional monomer such as polyallyl, poly(meth)acrylate, poly(meth)acrylamide, etc. The agent is encapsulated in a synthetic resin walled capsule such as polyether urethane, polyurea, etc. together with a colorless dye and optionally a solvent. After the image is enhanced, the colorless dye in the unexposed area is brought into contact with a color developer to color the image, and was developed by the present inventors.

(Examples of the Invention) Examples are shown below, but the present invention is not limited only to these examples.

Examples Co-anilino 3-methyl-6-N-ethyl-N-ynylaminofluoran 2P% Co-anilino 3-chloro-t-diethylaminofluoran Co 1
, r% polyvinyl alcohol (Kensha Tatachi, degree of polymerization 1000) was dispersed using a sand mill with an aqueous solution to an average particle size of μ.

On the other hand, the i,i-bis(4cm hydroxyphenyl)phthane 109% aZ-benzyloxynaphthalene t7f shown in the synthesis example was dispersed overnight in a ball mill together with a 3% polyvinyl alcohol aqueous solution 60F. Furthermore, 3% polyvinyl alcohol aqueous solution of β-p-methoxyphenoxyethyloxysalicylic acid ty% zinc oxide IOY! It is dispersed in a ball mill all day and night with rinsing. Furthermore, /, /, J-)
Lysu lambda'-methyl-hiro'-hydroxy-zl t
-Bunalphenylbutane Q, coflf:! % polyvinyl alcohol aqueous solution ljP overnight.

After mixing this well, use Josia Kaolin! Then, fine-particle silica 6F was added and dispersed well, and paraffin wax emulsion jO% dispersion (Middle East oil and fat Cello Sealuna≠, zr') ay was added to the coating liquid to prepare a coating liquid.

The coating liquid is ≠j y / m 2 Fine calcium carbonate having a basis weight of Jy / m 2 is coated on neutral paper with SDR as a binder, and the solid content coating amount is z,
It was applied so that the area was 617m2.

After drying at 60°C for 7 minutes, a super calender was applied at a linear pressure of jOKgW/l:m to obtain a coated paper (A).

The coated paper requires a heating energy of 31 mJ/
When the color was developed by heating with a Macbeth reflection densitometer to determine the color density, it was found to be 1. /! showed that.

The obtained recording material was free from fog during raw storage and had excellent stability over time.

On the other hand, the obtained color 1fIIe! is a clear black color, indicating that it is a chemical substance.
It showed good resistance to water and sunlight.

(Comparative Example) In the Example, bisphenol A was used in place of l,/-bis(couhydroxyphenyl)butane.The color density was determined to be 00.

Claims (1)

[Claims] A recording material that utilizes color development due to contact between an electron-donating colorless dye and an electron-accepting compound, characterized in that 1,1-bis(4-hydroxyphenyl)butane is used as the electron-accepting compound.