JP2018012270A - Heat-sensitive recording material - Google Patents
Heat-sensitive recording material Download PDFInfo
- Publication number
- JP2018012270A JP2018012270A JP2016143363A JP2016143363A JP2018012270A JP 2018012270 A JP2018012270 A JP 2018012270A JP 2016143363 A JP2016143363 A JP 2016143363A JP 2016143363 A JP2016143363 A JP 2016143363A JP 2018012270 A JP2018012270 A JP 2018012270A
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- JP
- Japan
- Prior art keywords
- heat
- sensitive recording
- recording material
- methyl
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 3-phenylureido Chemical group 0.000 claims abstract description 42
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Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Description
本発明は、発色画像の保存安定性に優れた感熱記録材料に関するものである。 The present invention relates to a heat-sensitive recording material excellent in storage stability of color images.
感熱記録材料は、一般にロイコ染料とフェノール性化合物等の顕色性化合物とをそれぞれ別個に微粒子状に分散化した後、両者を混合し、これに結合剤、増感剤、充填剤、滑剤等の添加剤を添加して得られた塗工液を、紙、フィルム、合成紙等に塗布したもので、加熱によりロイコ染料と顕色性化合物の一方又は両者が溶融、接触して起こる化学反応により発色記録を得るものである。このような感熱記録材料の発色のためには、サーマルヘッドを内蔵したサーマルプリンター等が用いられる。この感熱記録法は他の記録法に比較して、（１）記録時に騒音が出ない、（２）現像、定着の必要がない、（３）メンテナンスフリーである、（４）機械が比較的安価である等の特徴により、ファクシミリ分野、コンピューターのアウトプット、電卓などのプリンター分野、医療計測用のレコーダー分野、自動券売機分野、感熱記録型ラベル分野等に広く用いられている。 In general, heat-sensitive recording materials are obtained by dispersing a leuco dye and a developing compound such as a phenolic compound into fine particles separately, and then mixing both of them together with a binder, sensitizer, filler, lubricant, etc. A chemical reaction that occurs when one or both of the leuco dye and the color developing compound is melted and brought into contact with heat by applying the coating liquid obtained by adding the additive to the paper, film, synthetic paper, etc. Thus, color recording is obtained. For the color development of such a heat-sensitive recording material, a thermal printer or the like with a built-in thermal head is used. Compared with other recording methods, this thermal recording method is (1) no noise during recording, (2) no need for development and fixing, (3) maintenance-free, (4) machine is relatively Due to its low cost, it is widely used in the facsimile field, the output of computers, the field of printers such as calculators, the field of recorders for medical measurement, the field of automatic ticket machines, the field of thermal recording labels, and the like.
近年、感熱記録材料の使用用途が拡大すると共に、小売店やスーパーマーケット等のＰＯＳシステム化、交通機関の自動化システムに伴いラベル類や乗車券、回数券等への使用が増加している。これらの用途において、水、ラップ類、プラスチックシート類、油、脂肪等に触れて生じる記録像（印字、画像、パターン）の耐水性、耐可塑剤性、耐油性等の保存性が必須条件となっている。また、より生産性を向上させるため高速記録に対する要求が一段と高くなり、高速記録に十分対応しうる感熱記録材料の開発が強く望まれている。この場合、融点が低く、融解熱の小さい顕色性化合物が必要だが、この性質は製造時、使用時あるいは保管時における感熱記録材料の未記録部の劣化（地肌かぶり）が起こりやすくなることから、高い白色度だけでなく未記録部の安定性の向上も強く望まれている。 In recent years, the use of heat-sensitive recording materials has expanded, and the use of labels, train tickets, coupon tickets, etc. has increased with the establishment of POS systems in retail stores and supermarkets and the automation systems for transportation facilities. In these applications, preservability such as water resistance, plasticizer resistance, and oil resistance of recorded images (prints, images, patterns) generated by touching water, wraps, plastic sheets, oil, fat, etc. is an essential condition. It has become. In addition, the demand for high-speed recording has further increased in order to improve productivity, and development of a heat-sensitive recording material that can sufficiently cope with high-speed recording is strongly desired. In this case, a color developing compound with a low melting point and a low heat of fusion is required, but this property is likely to cause deterioration of the unrecorded part (background fogging) of the heat-sensitive recording material during production, use or storage. Further, not only high whiteness but also improvement in stability of unrecorded portions is strongly desired.
一般にフェノール性水酸基を有する顕色性化合物は顕色能が高く、中でもビスフェノール系顕色性化合物は、発色濃度の高さから、例えば特許文献１に示される２，２−ビス（４−ヒドロキシフェニルプロパン）（ビスフェノールＡ）及び特許文献２に示される４，４’−ジヒドロキシジフェニルスルホン（ビスフェノールＳ）をはじめ、数多く報告されている。しかし、これらは耐水性に劣り、また地肌の劣化（地肌かぶり）等の欠点を有する。現状、発色画像部の保存安定性が十分とは言えず、更なる保存安定性の向上が望まれている。特に塩化ビニル製フィルムやプラスチックシート、消しゴムに含まれる可塑剤に対する画像安定性（耐可塑剤性）に劣ることから、この耐可塑剤性の向上も要望されている。 In general, a color developing compound having a phenolic hydroxyl group has a high color developing ability. Among them, a bisphenol type color developing compound has a high color density, and therefore, for example, 2,2-bis (4-hydroxyphenyl) disclosed in Patent Document 1 is used. Propane) (bisphenol A) and 4,4′-dihydroxydiphenyl sulfone (bisphenol S) disclosed in Patent Document 2 have been reported in large numbers. However, they are inferior in water resistance and have drawbacks such as deterioration of the background (background fogging). Currently, the storage stability of the color image portion is not sufficient, and further improvement in storage stability is desired. In particular, since the image stability (plasticizer resistance) with respect to a plasticizer contained in a vinyl chloride film, a plastic sheet, or an eraser is inferior, this improvement in plasticizer resistance is also demanded.
本発明は、前記の従来技術の欠点を解決することを目的に、画像部の保存安定性に優れた感熱記録材料を提供することにある。 An object of the present invention is to provide a heat-sensitive recording material excellent in storage stability of an image portion for the purpose of solving the above-mentioned drawbacks of the prior art.
本発明者は、前記の目的を達成すべく鋭意検討を重ねた結果、顕色性化合物として３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナートと特定の保存性向上剤を併用した感熱記録材料が画像部の保存安定性に優れることを新たに見出し、本発明を完成させたものである。 As a result of intensive studies to achieve the above object, the present inventor has obtained 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate and a specific preservability improver as a color developing compound. The present invention has been completed by newly finding that the heat-sensitive recording material used in combination is excellent in storage stability of the image area.
即ち本発明は、
［１］３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナートと少なくとも１種類の保存性向上剤を含有する事を特徴とする感熱記録材料、
［２］保存性向上剤が式（１）または式（２）で示される化合物のいずれかより選ばれる１種類である事を特徴とする［１］に記載の感熱記録材料、
［４］［１］乃至［３］のいずれか一つに記載の感熱記録材料を含む感熱記録層、
［５］［１］乃至［４］のいずれか一つに記載の感熱記録材料または感熱記録層を含む感熱記録紙、
に関する。
That is, the present invention
[1] A heat-sensitive recording material comprising 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate and at least one preservability improver;
[2] The heat-sensitive recording material according to [1], wherein the preservability improver is one kind selected from the compounds represented by formula (1) or formula (2),
[4] A thermal recording layer comprising the thermal recording material according to any one of [1] to [3],
[5] A thermal recording paper comprising the thermal recording material or thermal recording layer according to any one of [1] to [4],
About.
顕色性化合物として３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナートと特定の保存性向上剤を併用する事により、発色画像部が可塑剤に対し高い安定性を示す感熱記録材料を提供することができた。 Heat-sensitive color image portion shows high stability to plasticizer by using 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate as a color developing compound and a specific preservative improver. Recording material could be provided.
本発明を詳細に説明する。
本発明は、通常無色ないし単色の発色性化合物及び顕色性化合物として３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナート、上記式（１）または式（２）で示される化合物のいずれか１種類の保存性向上剤を使用し、必要に応じてその他の顕色性化合物、増感剤、保存性向上剤、さらには以下に示す結合剤及び必要に応じて充填剤、その他の添加物等を含む感熱記録材料に関する。
The present invention will be described in detail.
The present invention is generally represented by 3-((3-phenylureido) phenyl] = 4-methylbenzenesulfonate, the above formula (1) or formula (2) as a colorless to monochromatic coloring compound and a developing compound. Using any one kind of preservability improver of the compound, if necessary, other color developing compounds, sensitizers, preservability improvers, and further binders shown below and fillers as necessary, The present invention relates to a heat-sensitive recording material containing other additives.
本発明の感熱記録材料を形成するにあたり、発色性化合物は通常１〜５０質量％、好ましくは５〜３０質量％、３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナートは通常１〜７０質量％、好ましくは１０〜５０質量％、増感剤は１〜８０質量％、保存性向上剤は通常０．０１〜３０質量％、結合剤は通常１〜９０質量％、充填剤は通常０〜８０質量％、その他の滑剤、界面活性剤、消泡剤、紫外線吸収剤は各々任意の割合で、例えば通常各々０〜３０質量％が使用される（質量％は感熱記録材料中に占める各成分の質量比）。 In forming the heat-sensitive recording material of the present invention, the color forming compound is usually 1 to 50% by mass, preferably 5 to 30% by mass, and 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate is usually used. 1 to 70 mass%, preferably 10 to 50 mass%, sensitizer is 1 to 80 mass%, preservability improver is usually 0.01 to 30 mass%, binder is usually 1 to 90 mass%, filler Is usually 0 to 80% by mass, and other lubricants, surfactants, antifoaming agents, and ultraviolet absorbers are each in an arbitrary ratio, for example, 0 to 30% by mass is usually used (mass% is in the heat-sensitive recording material). Mass ratio of each component).
更に好ましい態様としては、上記の組成のうちで、３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナート１質量部に対して保存性向上剤は０．０１質量倍〜１０質量倍、好ましくは０．０３質量倍〜２．５質量倍の範囲で使用される。本発明の感熱記録材料においては、前記の成分以外のそれ自身が公知の顕色性化合物、増感剤又はその他の添加物を併用しても構わない。 As a more preferred embodiment, among the above compositions, the preservability improver is 0.01 mass times to 10 mass with respect to 1 part by mass of 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate. It is used in the range of double, preferably 0.03 mass times to 2.5 mass times. In the heat-sensitive recording material of the present invention, a known color developing compound, a sensitizer, or other additives other than the above-described components may be used in combination.
本発明に用いられる発色性化合物は、一般に感圧記録紙や感熱記録紙に用いられるものであればよく、特に制限されない。用いられる発色性化合物の例としては、例えばフルオラン系化合物、トリアリールメタン系化合物、スピロ系化合物、ジフェニルメタン系化合物、チアジン系化合物、ラクタム系化合物、フルオレン系化合物が挙げられ、フルオラン系化合物が好ましい。 The color-forming compound used in the present invention is not particularly limited as long as it is generally used for pressure-sensitive recording paper and heat-sensitive recording paper. Examples of the chromogenic compound used include fluoran compounds, triarylmethane compounds, spiro compounds, diphenylmethane compounds, thiazine compounds, lactam compounds, and fluorene compounds, with fluorane compounds being preferred.
フルオラン系化合物の具体例としては、例えば３−ジエチルアミノ−６−メチル−７−アニリノフルオラン、３−ジブチルアミノ−６−メチル−７−アニリノフルオラン、３−（Ｎ−メチル−Ｎ−シクロヘキシルアミノ）−６−メチル−７−アニリノフルオラン、３−（Ｎ−エチル−Ｎ−イソペンチルアミノ）−６−メチル−７−アニリノフルオラン、３−（Ｎ−エチル−Ｎ−イソブチルアミノ）−６−メチル−７−アニリノフルオラン、３−［Ｎ−エチル−Ｎ−（３−エトキシプロピル）アミノ］−６−メチル−７−アニリノフルオラン、３−（Ｎ−エチル−Ｎ−ヘキシルアミノ）−６−メチル−７−アニリノフルオラン、３−ジペンチルアミノ−６−メチル−７−アニリノフルオラン、３−（Ｎ−メチル−Ｎ−プロピルアミノ）−６−メチル−７−アニリノフルオラン、３−（Ｎ−エチル−Ｎ−テトラヒドロフリルアミノ）−６−メチル−７−アニリノフルオラン、３−ジエチルアミノ−６−メチル−７−（ｐ−クロロアニリノ）フルオラン、３−ジエチルアミノ−６−メチル−７−（ｐ−フルオロアニリノ）フルオラン、３−［Ｎ−エチル−Ｎ−（ｐ−トリル）アミノ］−６−メチル−７−アニリノフルオラン、３−ジエチルアミノ−６−メチル−７−（ｐ−トルイジノ）フルオラン、３−ジエチルアミノ−７−（ｏ−クロロアニリノ）フルオラン、３−ジブチルアミノ−７−（ｏ−クロロアニリノ）フルオラン、３−ジエチルアミノ−７−（ｏ−フルオロアニリノ）フルオラン、３−ジブチルアミノ−７−（ｏ−フルオロアニリノ）フルオラン、３−ジエチルアミノ−７−（３，４−ジクロロアニリノ）フルオラン、３−ピロリジノ−６−メチル−７−アニリノフルオラン、３−ジエチルアミノ−６−クロロ−７−エトキシエチルアミノフルオラン、３−ジエチルアミノ−６−クロロ−７−アニリノフルオラン、３−ジエチルアミノ−７−クロロフルオラン、３−ジエチルアミノ−７−メチルフルオラン、３−ジエチルアミノ−７−オクチルフルオラン、３−［Ｎ−エチル−Ｎ−（ｐ−トリル）アミノ］−６−メチル−７−フェネチルフルオラン等が挙げられ、３−ジブチルアミノ−６−メチル−７−アニリノフルオランが好ましい。 Specific examples of the fluorane compound include 3-diethylamino-6-methyl-7-anilinofluorane, 3-dibutylamino-6-methyl-7-anilinofluorane, 3- (N-methyl-N- Cyclohexylamino) -6-methyl-7-anilinofluorane, 3- (N-ethyl-N-isopentylamino) -6-methyl-7-anilinofluorane, 3- (N-ethyl-N-isobutyl) Amino) -6-methyl-7-anilinofluorane, 3- [N-ethyl-N- (3-ethoxypropyl) amino] -6-methyl-7-anilinofluorane, 3- (N-ethyl- N-hexylamino) -6-methyl-7-anilinofluorane, 3-dipentylamino-6-methyl-7-anilinofluorane, 3- (N-methyl-N-propylamino) -6-me Ru-7-anilinofluorane, 3- (N-ethyl-N-tetrahydrofurylamino) -6-methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7- (p-chloroanilino) fluorane 3-diethylamino-6-methyl-7- (p-fluoroanilino) fluorane, 3- [N-ethyl-N- (p-tolyl) amino] -6-methyl-7-anilinofluorane, 3- Diethylamino-6-methyl-7- (p-toluidino) fluorane, 3-diethylamino-7- (o-chloroanilino) fluorane, 3-dibutylamino-7- (o-chloroanilino) fluorane, 3-diethylamino-7- (o -Fluoroanilino) fluorane, 3-dibutylamino-7- (o-fluoroanilino) fluorane, 3-diethylamino-7- 3,4-dichloroanilino) fluorane, 3-pyrrolidino-6-methyl-7-anilinofluorane, 3-diethylamino-6-chloro-7-ethoxyethylaminofluorane, 3-diethylamino-6-chloro-7 -Anilinofluorane, 3-diethylamino-7-chlorofluorane, 3-diethylamino-7-methylfluorane, 3-diethylamino-7-octylfluorane, 3- [N-ethyl-N- (p-tolyl) Amino] -6-methyl-7-phenethylfluorane and the like, and 3-dibutylamino-6-methyl-7-anilinofluorane is preferred.
トリアリールメタン系化合物の具体例としては、例えば３，３−ビス（ｐ−ジメチルアミノフェニル）−６−ジメチルアミノフタリド（別名：クリスタルバイオレットラクトン又はＣＶＬ）、３，３−ビス（ｐ−ジメチルアミノフェニル）フタリド、３−（ｐ−ジメチルアミノフェニル）−３−（１，２−ジメチルアミノインドール−３−イル）フタリド、３−（ｐ−ジメチルアミノフェニル）−３−（２−メチルインドール−３−イル）フタリド、３−（ｐ−ジメチルアミノフェニル）−３−（２−フェニルインドール−３−イル）フタリド、３，３−ビス（１，２−ジメチルインドール−３−イル）−５−ジメチルアミノフタリド、３，３−ビス（１，２−ジメチルインドール−３−イル）−６−ジメチルアミノフタリド、３，３−ビス（９−エチルカルバゾール−３−イル）−５−ジメチルアミノフタリド、３，３−（２−フェニルインドール−３−イル）−５−ジメチルアミノフタリド、３−ｐ−ジメチルアミノフェニル−３−（１−メチルピロール−２−イル）−６−ジメチルアミノフタリド等が挙げられる。 Specific examples of triarylmethane compounds include, for example, 3,3-bis (p-dimethylaminophenyl) -6-dimethylaminophthalide (also known as crystal violet lactone or CVL), 3,3-bis (p-dimethyl). Aminophenyl) phthalide, 3- (p-dimethylaminophenyl) -3- (1,2-dimethylaminoindol-3-yl) phthalide, 3- (p-dimethylaminophenyl) -3- (2-methylindole- 3-yl) phthalide, 3- (p-dimethylaminophenyl) -3- (2-phenylindol-3-yl) phthalide, 3,3-bis (1,2-dimethylindol-3-yl) -5 Dimethylaminophthalide, 3,3-bis (1,2-dimethylindol-3-yl) -6-dimethylaminophthalide, 3,3-bis 9-ethylcarbazol-3-yl) -5-dimethylaminophthalide, 3,3- (2-phenylindol-3-yl) -5-dimethylaminophthalide, 3-p-dimethylaminophenyl-3- ( 1-methylpyrrol-2-yl) -6-dimethylaminophthalide and the like.
スピロ系化合物の具体例としては、例えば３−メチルスピロジナフトピラン、３−エチルスピロジナフトピラン、３，３’−ジクロロスピロジナフトピラン、３−ベンジルスピロジナフトピラン、３−プロピルスピロベンゾピラン、３−メチルナフト−（３−メトキシベンゾ）スピロピラン、１，３，３−トリメチル−６−ニトロ−８’−メトキシスピロ（インドリン−２，２’−ベンゾピラン）等；ジフェニルメタン系化合物の具体例としては、例えばＮ−ハロフェニル−ロイコオーラミン、４，４−ビス−ジメチルアミノフェニルベンズヒドリルベンジルエーテル、Ｎ−２，４，５−トリクロロフェニルロイコオーラミン等；チアジン系化合物の具体例としては、例えばベンゾイルロイコメチレンブルー、ｐ−ニトロベンゾイルロイコメチレンブルー等；ラクタム系化合物の具体例としては、例えばローダミンＢアニリノラクタム、ローダミンＢ−ｐ−クロロアニリノラクタム等；フルオレン系化合物の具体例としては、例えば３，６−ビス（ジメチルアミノ）フルオレンスピロ（９，３’）−６’−ジメチルアミノフタリド、３，６−ビス（ジメチルアミノ）フルオレンスピロ（９，３’）−６’−ピロリジノフタリド、３−ジメチルアミノ−６−ジエチルアミノフルオレンスピロ（９，３’）−６’−ピロリジノフタリド等、が挙げられる。これらの発色性化合物は単独もしくは混合して用いられる。 Specific examples of the spiro compound include, for example, 3-methylspirodinaphthopyran, 3-ethylspirodinaphthopyran, 3,3′-dichlorospirodinaphthopyran, 3-benzylspirodinaphthopyran, 3-propylspirobenzo. Pyran, 3-methylnaphtho- (3-methoxybenzo) spiropyran, 1,3,3-trimethyl-6-nitro-8′-methoxyspiro (indoline-2,2′-benzopyran), etc .; specific examples of diphenylmethane compounds Are, for example, N-halophenyl-leucooramine, 4,4-bis-dimethylaminophenylbenzhydrylbenzyl ether, N-2,4,5-trichlorophenylleucooramine, and the like. Specific examples of thiazine compounds include For example, benzoylleucomethylene blue, p-nitrobenzoylleucome Specific examples of lactam compounds include, for example, rhodamine B anilinolactam, rhodamine Bp-chloroanilinolactam, etc .; specific examples of fluorene compounds include, for example, 3,6-bis (dimethylamino) fluorene Spiro (9,3 ′)-6′-dimethylaminophthalide, 3,6-bis (dimethylamino) fluorene spiro (9,3 ′)-6′-pyrrolidinophthalide, 3-dimethylamino-6-diethylamino Fluorene spiro (9,3 ′)-6′-pyrrolidinophthalide and the like. These color forming compounds are used alone or in combination.
本発明において併用可能な顕色性化合物としては、特に制限されないが、一般に感圧記録紙や感熱記録紙に用いられているものであればよく、例えばα−ナフトール、β−ナフトール、ｐ−オクチルフェノール、４−ｔｅｒｔ−オクチルフェノール、ｐ−ｔｅｒｔ−ブチルフェノール、ｐ−フェニルフェノール、１，１−ビス（ｐ−ヒドロキシフェニル）プロパン、２，２−ビス（ｐ−ヒドロキシフェニル）プロパン（別名：ビスフェノールＡ又はＢＰＡ）、２，２−ビス（ｐ−ヒドロキシフェニル）ブタン、１，１−ビス（ｐ−ヒドロキシフェニル）シクロヘキサン、４，４’−チオビスフェノール、４，４’−シクロ−ヘキシリデンジフェノール、２，２’−ビス（２，５−ジブロム−４−ヒドロキシフェニル）プロパン、４，４’−イソプロピリデンビス（２−ｔｅｒｔ−ブチルフェノール）、２，２’−メチレンビス（４−クロロフェノール）、４，４’−ジヒドロキシジフェニルスルホン、４−ヒドロキシ−４’−メトキシジフェニルスルホン、２，４’−ジヒドロキシジフェニルスルホン、４−ヒドロキシ−４’−イソプロポキシジフェニルスルホン、４−ヒドロキシ−４’−エトキシジフェニルスルホン、４−ヒドロキシ−４’−ブトキシジフェニルスルホン、４−ヒドロキシ−４’−ベンジルオキシジフェニルスルホン、ビス（４−ヒドロキシフェニル）酢酸メチル、ビス（４−ヒドロキシフェニル）酢酸ブチル、ビス（４−ヒドロキシフェニル）酢酸ベンジル、２，４−ジヒドロキシ−２’−メトキシベンズアニリド等のフェノール性化合物、ｐ−ヒドロキシ安息香酸ベンジル、ｐ−ヒドロキシ安息香酸エチル、４−ヒドロキシフタル酸ジベンジル、４−ヒドロキシフタル酸ジメチル、５−ヒドロキシイソフタル酸エチル、３，５−ジ−ｔｅｒｔ−ブチルサリチル酸、３，５−ジ−α−メチルベンジルサリチル酸等の芳香族カルボン酸誘導体、芳香族カルボン酸又はその多価金属塩等が挙げられる。 The color developing compound that can be used in combination in the present invention is not particularly limited, and may be any compound that is generally used for pressure-sensitive recording paper and heat-sensitive recording paper. For example, α-naphthol, β-naphthol, p-octylphenol. 4-tert-octylphenol, p-tert-butylphenol, p-phenylphenol, 1,1-bis (p-hydroxyphenyl) propane, 2,2-bis (p-hydroxyphenyl) propane (also known as bisphenol A or BPA) ), 2,2-bis (p-hydroxyphenyl) butane, 1,1-bis (p-hydroxyphenyl) cyclohexane, 4,4′-thiobisphenol, 4,4′-cyclo-hexylidene diphenol, 2, 2'-bis (2,5-dibromo-4-hydroxyphenyl) propane, 4,4'-iso Propylidenebis (2-tert-butylphenol), 2,2'-methylenebis (4-chlorophenol), 4,4'-dihydroxydiphenylsulfone, 4-hydroxy-4'-methoxydiphenylsulfone, 2,4'-dihydroxydiphenylsulfone 4-hydroxy-4′-isopropoxydiphenylsulfone, 4-hydroxy-4′-ethoxydiphenylsulfone, 4-hydroxy-4′-butoxydiphenylsulfone, 4-hydroxy-4′-benzyloxydiphenylsulfone, bis (4 Phenolic compounds such as -hydroxyphenyl) methyl acetate, bis (4-hydroxyphenyl) butyl acetate, bis (4-hydroxyphenyl) acetate benzyl, 2,4-dihydroxy-2'-methoxybenzanilide, p-hydroxybenzoate Benzyl acid, ethyl p-hydroxybenzoate, dibenzyl 4-hydroxyphthalate, dimethyl 4-hydroxyphthalate, ethyl 5-hydroxyisophthalate, 3,5-di-tert-butylsalicylic acid, 3,5-di-α- Examples thereof include aromatic carboxylic acid derivatives such as methylbenzyl salicylic acid, aromatic carboxylic acids or polyvalent metal salts thereof.
本発明において用いられる増感剤（熱可融性化合物）の具体例としては、動植物性ワックス、合成ワックス等のワックス類や高級脂肪酸、高級脂肪酸アミド、高級脂肪酸アニリド、ナフタレン誘導体、芳香族エーテル、芳香族カルボン酸誘導体、芳香族スルホン酸エステル誘導体、炭酸またはシュウ酸ジエステル誘導体、ビフェニル誘導体、ターフェニル誘導体、スルホン誘導体、芳香族ケトン誘導体、芳香族炭化水素化合物等が挙げられる。 Specific examples of the sensitizer (thermofusible compound) used in the present invention include waxes such as animal and vegetable waxes and synthetic waxes, higher fatty acids, higher fatty acid amides, higher fatty acid anilides, naphthalene derivatives, aromatic ethers, Examples include aromatic carboxylic acid derivatives, aromatic sulfonic acid ester derivatives, carbonic acid or oxalic acid diester derivatives, biphenyl derivatives, terphenyl derivatives, sulfone derivatives, aromatic ketone derivatives, and aromatic hydrocarbon compounds.
ワックス類の具体例としては、例えば木ろう、カルナウバろう、シェラック、パラフィン、モンタンろう、酸化パラフィン、ポリエチレンワックス、酸化ポリエチレン等；高級脂肪酸としては、例えばステアリン酸、ベヘン酸等；高級脂肪酸アミドとしては、例えばステアリン酸アミド、オレイン酸アミド、Ｎ−メチルステアリン酸アミド、エルカ酸アミド、メチロールベヘン酸アミド、メチレンビスステアリン酸アミド、エチレンビスステアリン酸アミド等；高級脂肪酸アニリドとしては、例えばステアリン酸アニリド、リノール酸アニリド等；ナフタレン誘導体としては、例えば１−ベンジルオキシナフタレン、２−ベンジルオキシナフタレン、１−ヒドロキシナフトエ酸フェニルエステル等；芳香族エーテルとしては、例えば１，２−ジフェノキシエタン、１，４−ジフェノキシブタン、１，２−ビス（３−メチルフェノキシ）エタン、１，２−ビス（４−メトキシフェノキシ）エタン、１，２−ビス（３，４−ジメチルフェニル）エタン、１−フェノキシ−２−（４−クロロフェノキシ）エタン、１−フェノキシ−２−（４−メトキシフェノキシ）エタン、１，２−ジフェノキシメチルベンゼン等；芳香族カルボン酸誘導体としては、例えばｐ−ヒドロキシ安息香酸ベンジルエステル、ｐ−ベンジルオキシ安息香酸ベンジルエステル、テレフタル酸ジベンジルエステル等；芳香族スルホン酸エステル誘導体としては、例えばｐ−トルエンスルホン酸フェニルエステル、フェニルメシチレンスルホナート、４−メチルフェニルメシチレンスルホナート等；炭酸又はシュウ酸ジエステル誘導体としては、例えば炭酸ジフェニル、シュウ酸ジベンジルエステル、シュウ酸ジ（４−クロロベンジル）エステル、シュウ酸ジ（４−メチルベンジル）エステル誘導体；ビフェニル誘導体としては、例えばｐ−ベンジルビフェニル、ｐ−アリルオキシビフェニル等；ターフェニル誘導体としては、例えばｍ−ターフェニル等；スルホン誘導体としては、例えばジフェニルスルホン等、が挙げられる。 Specific examples of waxes include, for example, wood wax, carnauba wax, shellac, paraffin, montan wax, oxidized paraffin, polyethylene wax, polyethylene oxide, etc .; higher fatty acids such as stearic acid, behenic acid, etc .; higher fatty acid amides For example, stearic acid amide, oleic acid amide, N-methyl stearic acid amide, erucic acid amide, methylol behenic acid amide, methylene bis stearic acid amide, ethylene bis stearic acid amide, etc .; Linoleic acid anilide, etc .; As naphthalene derivatives, for example, 1-benzyloxynaphthalene, 2-benzyloxynaphthalene, 1-hydroxynaphthoic acid phenyl ester, etc .; As aromatic ethers, for example, 1,2- Phenoxyethane, 1,4-diphenoxybutane, 1,2-bis (3-methylphenoxy) ethane, 1,2-bis (4-methoxyphenoxy) ethane, 1,2-bis (3,4-dimethylphenyl) Ethane, 1-phenoxy-2- (4-chlorophenoxy) ethane, 1-phenoxy-2- (4-methoxyphenoxy) ethane, 1,2-diphenoxymethylbenzene, etc .; examples of aromatic carboxylic acid derivatives include p -Hydroxybenzoic acid benzyl ester, p-benzyloxybenzoic acid benzyl ester, terephthalic acid dibenzyl ester, etc .; examples of aromatic sulfonic acid ester derivatives include p-toluenesulfonic acid phenyl ester, phenylmesitylene sulfonate, 4-methylphenyl Mesitylene sulfonate, etc .; carbonic acid or dioxalic acid Examples of steal derivatives include diphenyl carbonate, oxalic acid dibenzyl ester, oxalic acid di (4-chlorobenzyl) ester, oxalic acid di (4-methylbenzyl) ester derivative; and biphenyl derivatives such as p-benzyl biphenyl, p -Allyloxybiphenyl and the like; Examples of the terphenyl derivative include m-terphenyl and the like; Examples of the sulfone derivative include diphenylsulfone and the like.
本発明に用いられる保存性向上剤の具体例としては、例えば２，２’−メチレンビス（４−メチル−６−ｔｅｒｔ−ブチルフェノール）、２，２’−メチレンビス（４−エチル−６−ｔｅｒｔ−ブチルフェノール）、２，２’−エチリデンビス（４，６−ジ−ｔｅｒｔ−ブチルフェノール）、４，４’−チオビス（２−メチル−６−ｔｅｒｔ−ブチルフェノール）、４，４’−ブチリデンビス（６−ｔｅｒｔ−ブチル−ｍ−クレゾール）、１−〔α−メチル−α−（４’−ヒドロキシフェニル）エチル〕−４−〔α’，α’−ビス（４’−ヒドロキシフェニル）エチル〕ベンゼン、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−シクロヘキシルフェニル）ブタン、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−ｔｅｒｔ−ブチルフェニル）ブタン、トリス（２，６−ジメチル−４−ｔｅｒｔ−ブチル−３−ヒドロキシベンジル）イソシアヌレート、４，４’−チオビス（３−メチルフェノール）、４，４’−ジヒドロキシ−３，３’，５，５’−テトラブロモジフェニルスルホン、４，４’−ジヒドロキシ−３，３’，５，５’−テトラメチルジフェニルスルホン、２，２−ビス（４−ヒドロキシ−３，５−ジブロモフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジクロロフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジメチルフェニル）プロパン等のヒンダードフェノール化合物、１，４−ジグリシジルオキシベンゼン、４，４’−ジグリシジルオキシジフェニルスルホン、４−ベンジルオキシ−４’−（２−メチルグリシジルオキシ）ジフェニルスルホン、テレフタル酸ジグリシジル、クレゾールノボラック型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、ビスフェノールＡ型エポキシ樹脂等のエポキシ化合物、Ｎ，Ｎ’−ジ−２−ナフチル−ｐ−フェニレンジアミン、２，２’−メチレンビス（４，６−ジ−ｔｅｒｔ−ブチルフェニル）ホスフェイトのナトリウムまたは多価金属塩、ビス（４−エチレンイミノカルボニルアミノフェニル）メタン等が挙げられる。例えば２，２’−メチレンビス（４−メチル−６−ｔｅｒｔ−ブチルフェノール）、２，２’−メチレンビス（４−エチル−６−ｔｅｒｔ−ブチルフェノール）、２，２’−エチリデンビス（４，６−ジ−ｔｅｒｔ−ブチルフェノール）、４，４’−チオビス（２−メチル−６−ｔｅｒｔ−ブチルフェノール）、４，４’−ブチリデンビス（６−ｔｅｒｔ−ブチル−ｍ−クレゾール）、１−〔α−メチル−α−（４’−ヒドロキシフェニル）エチル〕−４−〔α’，α’−ビス（４’−ヒドロキシフェニル）エチル〕ベンゼン、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−シクロヘキシルフェニル）ブタン、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−ｔｅｒｔ−ブチルフェニル）ブタン、トリス（２，６−ジメチル−４−ｔｅｒｔ−ブチル−３−ヒドロキシベンジル）イソシアヌレート、４，４’−チオビス（３−メチルフェノール）、４，４’−ジヒドロキシ−３，３’，５，５’−テトラブロモジフェニルスルホン、４，４’−ジヒドロキシ−３，３’，５，５’−テトラメチルジフェニルスルホン、２，２−ビス（４−ヒドロキシ−３，５−ジブロモフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジクロロフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジメチルフェニル）プロパン等のヒンダードフェノール化合物、１，４−ジグリシジルオキシベンゼン、４，４’−ジグリシジルオキシジフェニルスルホン、４−ベンジルオキシ−４’−（２−メチルグリシジルオキシ）ジフェニルスルホン、テレフタル酸ジグリシジル、クレゾールノボラック型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、ビスフェノールＡ型エポキシ樹脂等のエポキシ化合物、Ｎ，Ｎ’−ジ−２−ナフチル−ｐ−フェニレンジアミン、２，２’−メチレンビス（４，６−ジ−ｔｅｒｔ−ブチルフェニル）ホスフェイトのナトリウムまたは多価金属塩、ビス（４−エチレンイミノカルボニルアミノフェニル）メタン、式（１）及び式（２）で示される化合物等が挙げられ、式（１）及び式（２）で示される化合物が特に好ましい。 Specific examples of the storage stability improver used in the present invention include, for example, 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-ethyl-6-tert-butylphenol). ), 2,2′-ethylidenebis (4,6-di-tert-butylphenol), 4,4′-thiobis (2-methyl-6-tert-butylphenol), 4,4′-butylidenebis (6-tert- Butyl-m-cresol), 1- [α-methyl-α- (4′-hydroxyphenyl) ethyl] -4- [α ′, α′-bis (4′-hydroxyphenyl) ethyl] benzene, 1,1 , 3-Tris (2-methyl-4-hydroxy-5-cyclohexylphenyl) butane, 1,1,3-tris (2-methyl-4-hydroxy-5-tert- Tilphenyl) butane, tris (2,6-dimethyl-4-tert-butyl-3-hydroxybenzyl) isocyanurate, 4,4′-thiobis (3-methylphenol), 4,4′-dihydroxy-3,3 ′ , 5,5′-tetrabromodiphenylsulfone, 4,4′-dihydroxy-3,3 ′, 5,5′-tetramethyldiphenylsulfone, 2,2-bis (4-hydroxy-3,5-dibromophenyl) Hindered phenol compounds such as propane, 2,2-bis (4-hydroxy-3,5-dichlorophenyl) propane, 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane, 1,4-di Glycidyloxybenzene, 4,4′-diglycidyloxydiphenyl sulfone, 4-benzyloxy-4 ′-(2-methylglycidyl (Luoxy) diphenyl sulfone, diglycidyl terephthalate, cresol novolac epoxy resin, phenol novolac epoxy resin, bisphenol A epoxy resin, N, N′-di-2-naphthyl-p-phenylenediamine, 2,2 Examples include sodium or polyvalent metal salts of '-methylenebis (4,6-di-tert-butylphenyl) phosphate, bis (4-ethyleneiminocarbonylaminophenyl) methane, and the like. For example, 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 2,2'-methylenebis (4-ethyl-6-tert-butylphenol), 2,2'-ethylidenebis (4,6-di-) -Tert-butylphenol), 4,4'-thiobis (2-methyl-6-tert-butylphenol), 4,4'-butylidenebis (6-tert-butyl-m-cresol), 1- [α-methyl-α -(4'-hydroxyphenyl) ethyl] -4- [α ', α'-bis (4'-hydroxyphenyl) ethyl] benzene, 1,1,3-tris (2-methyl-4-hydroxy-5- Cyclohexylphenyl) butane, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, tris (2,6-dimethyl) 4-tert-butyl-3-hydroxybenzyl) isocyanurate, 4,4′-thiobis (3-methylphenol), 4,4′-dihydroxy-3,3 ′, 5,5′-tetrabromodiphenylsulfone, 4 , 4′-dihydroxy-3,3 ′, 5,5′-tetramethyldiphenylsulfone, 2,2-bis (4-hydroxy-3,5-dibromophenyl) propane, 2,2-bis (4-hydroxy-) Hindered phenol compounds such as 3,5-dichlorophenyl) propane and 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane, 1,4-diglycidyloxybenzene, 4,4′-diglycidyloxy Diphenylsulfone, 4-benzyloxy-4 ′-(2-methylglycidyloxy) diphenylsulfone, diglyceryl terephthalate Sidyl, cresol novolac type epoxy resin, phenol novolac type epoxy resin, epoxy compound such as bisphenol A type epoxy resin, N, N′-di-2-naphthyl-p-phenylenediamine, 2,2′-methylenebis (4,6 -Di-tert-butylphenyl) phosphate sodium or polyvalent metal salt, bis (4-ethyleneiminocarbonylaminophenyl) methane, compounds represented by formula (1) and formula (2), etc. And compounds represented by formula (2) are particularly preferred.
本発明に用いられる結合剤の具体例としては、例えばメチルセルロース、メトキシセルロース、ヒドロキシエチルセルロース、カルボキシメチルセルロース、ナトリウムカルボキシメチルセルロース、セルロース、ポリビニルアルコール（ＰＶＡ）、カルボキシル基変性ポリビニルアルコール、スルホン酸基変性ポリビニルアルコール、シリル基変性ポリビニルアルコール、ポリビニルピロリドン、ポリアクリルアミド、ポリアクリル酸、デンプン及びその誘導体、カゼイン、ゼラチン、水溶性イソプレンゴム、スチレン／無水マレイン酸共重合体のアルカリ塩、イソ（又はジイソ）ブチレン／無水マレイン酸共重合体のアルカリ塩等の水溶性のもの或は（メタ）アクリル酸エステル共重合体、スチレン／（メタ）アクリル酸エステル共重合体、ポリウレタン、ポリエステル系ポリウレタン、ポリエーテル系ポリウレタン、ポリ酢酸ビニル、エチレン／酢酸ビニル共重合体、ポリ塩化ビニル、塩化ビニル／酢酸ビニル共重合体、ポリ塩化ビニリデン、ポリスチレン、スチレン／ブタジエン（ＳＢ）共重合体、カルボキシル化スチレン／ブタジエン（ＳＢ）共重合体、スチレン／ブタジエン／アクリル酸系共重合体、アクリロニトリル／ブタジエン（ＮＢ）共重合体、カルボキシル化アクリロニトリル／ブタジエン（ＮＢ）共重合体、コロイダルシリカと（メタ）アクリル樹脂の複合体粒子等の疎水性高分子エマルジョン等が挙げられる。 Specific examples of the binder used in the present invention include, for example, methyl cellulose, methoxy cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, cellulose, polyvinyl alcohol (PVA), carboxyl group-modified polyvinyl alcohol, sulfonic acid group-modified polyvinyl alcohol, Silyl group-modified polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, polyacrylic acid, starch and derivatives thereof, casein, gelatin, water-soluble isoprene rubber, alkali salt of styrene / maleic anhydride copolymer, iso (or diiso) butylene / anhydrous Water-soluble maleic acid copolymer such as alkali salt, (meth) acrylic acid ester copolymer, styrene / (meth) acrylic acid ester copolymer , Polyurethane, polyester polyurethane, polyether polyurethane, polyvinyl acetate, ethylene / vinyl acetate copolymer, polyvinyl chloride, vinyl chloride / vinyl acetate copolymer, polyvinylidene chloride, polystyrene, styrene / butadiene (SB) Polymer, carboxylated styrene / butadiene (SB) copolymer, styrene / butadiene / acrylic acid copolymer, acrylonitrile / butadiene (NB) copolymer, carboxylated acrylonitrile / butadiene (NB) copolymer, colloidal silica And hydrophobic polymer emulsions such as composite particles of (meth) acrylic resin.
本発明に用いられる充填剤の具体例としては、例えば炭酸カルシウム、炭酸マグネシウム、酸化マグネシウム、シリカ、ホワイトカーボン、タルク、クレー、アルミナ、水酸化マグネシウム、水酸化アルミニウム、酸化アルミニウム、硫酸バリウム、ポリスチレン樹脂、尿素−ホルマリン樹脂等が挙げられる。 Specific examples of the filler used in the present invention include, for example, calcium carbonate, magnesium carbonate, magnesium oxide, silica, white carbon, talc, clay, alumina, magnesium hydroxide, aluminum hydroxide, aluminum oxide, barium sulfate, polystyrene resin. And urea-formalin resin.
更に本発明においては上記以外の種々の添加剤を使用することができ、例えばサーマルヘッド磨耗防止、スティッキング防止等の目的でのステアリン酸亜鉛、ステアリン酸カルシウム等の高級脂肪酸金属塩、酸化防止あるいは老化防止効果を付与する為のフェノール誘導体、ベンゾフェノン系化合物、ベンゾトリアゾール系化合物等の紫外線吸収剤、各種の界面活性剤、消泡剤、等が挙げられる。 Furthermore, various additives other than those described above can be used in the present invention. For example, higher fatty acid metal salts such as zinc stearate and calcium stearate for the purpose of preventing thermal head wear and sticking, and preventing oxidation or aging. Examples thereof include ultraviolet absorbers such as phenol derivatives, benzophenone compounds, and benzotriazole compounds for imparting effects, various surfactants, and antifoaming agents.
次に、本発明の感熱記録材料の調製方法を説明する。本発明に用いられる、発色性化合物や顕色性化合物の３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナートを、それぞれ別々に結合剤あるいは必要に応じてその他の添加剤等と共にボールミル、アトライター、サンドミル等の分散機にて粉砕、分散化し分散液とした後（通常、粉砕や分散を湿式で行うときは水を媒体として用いる）、分散液を混合して感熱記録層塗布液を調製し、紙（普通紙、上質紙、コート紙等が使用出来る）、プラスチックシート、合成紙等の支持体上に通常乾燥質量で１〜２０ｇ／ｍ２になるようにバーコーター、ブレードコーター等により塗布、乾燥して本発明の感熱記録材料を作製する。 Next, a method for preparing the heat-sensitive recording material of the present invention will be described. The chromogenic compound and the color developing compound, 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate, which are used in the present invention, are separately bonded to each other, or other additives as required. And pulverize and disperse with a disperser such as a ball mill, attritor, sand mill, etc. to form a dispersion (usually water is used as a medium when pulverization or dispersion is performed in a wet manner), and then the dispersion is mixed to form a heat-sensitive recording layer A coating liquid is prepared, and a bar coater is used so that the dry weight is usually 1 to 20 g / m 2 on a support such as paper (plain paper, fine paper, coated paper, etc.), plastic sheet, synthetic paper, etc. The heat-sensitive recording material of the present invention is produced by applying and drying with a blade coater or the like.
また、必要に応じて感熱記録層と支持体の間に中間層を設けたり、感熱記録層上にオーバーコート層（保護層）を設けても良い。中間層、オーバーコート層（保護層）は、例えば前記の結合剤あるいは必要に応じてその他の添加物と共に、感熱記録層塗布液の調製におけるのと同様に必要に応じて粉砕、分散して中間層用塗布液又はオーバーコート層（保護層）用塗布液とした後、乾燥時の質量で通常０．１〜１０ｇ／ｍ２程度となるように塗布し、乾燥することにより設けられる。 If necessary, an intermediate layer may be provided between the heat-sensitive recording layer and the support, or an overcoat layer (protective layer) may be provided on the heat-sensitive recording layer. The intermediate layer and the overcoat layer (protective layer) are crushed and dispersed as necessary in the same manner as in the preparation of the thermal recording layer coating solution, for example, together with the above-mentioned binder or other additives as necessary. After the layer coating liquid or the overcoat layer (protective layer) coating liquid is applied, the coating is applied so that the mass during drying is usually about 0.1 to 10 g / m 2 and dried.
以下、本発明を実施例によって更に具体的に説明するが、本発明は、以下の実施例によって何ら限定されるものではない。実施例中「部」は質量部、溶液の説明における「％」は質量％である。 EXAMPLES Hereinafter, although an Example demonstrates this invention further more concretely, this invention is not limited at all by the following examples. In the examples, “parts” are parts by mass, and “%” in the description of the solution is mass%.
［合成例１］顕色性化合物３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナートの合成方法
［工程１］
ＭＳ（ＥＳＩ）：［Ｍ＋Ｈ］＋：ｃａｌ．：２６４．１，ｆｏｕｎｄ：２６４．１
[Synthesis Example 1] Method for synthesizing the color developing compound 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate [Step 1]
MS (ESI): [M + H] + : cal. : 264.1, found: 264.1
［工程２］
ＭＳ（ＥＳＩ）：［Ｍ−Ｈ］−：ｃａｌ．：３８１．１，ｆｏｕｎｄ：３８１．１
[Step 2]
MS (ESI): [M−H] − : cal. : 381.1, found: 381.1
［実施例１］ 感熱記録材料の作成
上記化合物［１０２］の３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナートを以下の組成で安井器械（株）製のマルチビーズショッカー（型式：ＰＶ１００１（Ｓ））を用いて１時間粉砕、分散化して［Ａ］液を調製した。
[Example 1] Preparation of heat-sensitive recording material 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate of the above compound [102] with the following composition, a multi-bead shocker (manufactured by Yasui Kikai Co., Ltd.) [Model A: PV1001 (S)) was ground and dispersed for 1 hour to prepare [A] solution.
［Ａ］液：３−［（３−フェニルウレイド）フェニル］＝４−メチル
ベンゼンスルホナート ２５部
２５％ＰＶＡ水溶液 ２０部
水 ５５部
[A] Liquid: 3-[(3-phenylureido) phenyl] = 4-methyl
Benzene sulfonate 25 parts
20 parts of 25% PVA aqueous solution
55 parts of water
下記組成の混合物をサンドグラインダーによりレーザー回析／散乱式粒子径分布測定装置ＬＡ−９５０（株式会社堀場製作所）によるメディアン粒子径が１μｍになるように粉砕、分散化して発色性化合物の分散液［Ｂ］を調製した。
［Ｂ］液：３−ジブチルアミノ−６−メチル−７−アニリノフルオラン ３５部
１５％ＰＶＡ水溶液 ４０部
水 ２５部
A mixture of the following composition was pulverized and dispersed with a sand grinder using a laser diffraction / scattering particle size distribution measuring apparatus LA-950 (Horiba, Ltd.) so that the median particle diameter was 1 μm, and a dispersion of a chromogenic compound [ B] was prepared.
[B] Liquid: 35 parts of 3-dibutylamino-6-methyl-7-anilinofluorane
40 parts of 15% PVA aqueous solution
25 parts of water
下記組成の混合物をサンドグラインダーによりレーザー回析／散乱式粒子径分布測定装置ＬＡ−９５０（株式会社堀場製作所）によるメディアン粒子径が１μｍになるように粉砕、分散化して保存性向上剤の分散液［Ｃ］を調製した。
［Ｃ］液：式（１）の化合物（日本曹達） ２５部
１５％ＰＶＡ水溶液 ２０部
水 ５５部
A mixture of the following composition was pulverized and dispersed with a sand grinder using a laser diffraction / scattering particle size distribution measuring apparatus LA-950 (Horiba, Ltd.) so that the median particle diameter was 1 μm. [C] was prepared.
[C] Liquid: Compound of formula (1) (Nippon Soda) 25 parts
20 parts of 15% PVA aqueous solution
55 parts of water
次いで、上記で得られた各液及び下記する薬剤を下記の組成で混合して感熱記録材料塗布液を調製し、坪量５０ｇ／ｍ２の上質紙上に乾燥時の質量が５ｇ／ｍ２となるように塗布、乾燥して本発明の感熱記録材料を作製した。
［Ａ］液 ２４．０部
［Ｂ］液 ８．６部
［Ｃ］液 ８．０部
６７％炭酸カルシウム水分散液 ９．０部
４８％変性スチレン・ブタジエン共重合体ラテックス ６．３部
水 ４４．１部
Next, each liquid obtained above and the following chemicals were mixed in the following composition to prepare a heat-sensitive recording material coating liquid, and the weight when dried on a fine paper having a basis weight of 50 g / m 2 was 5 g / m 2 . The heat-sensitive recording material of the present invention was prepared by coating and drying.
[A] Liquid 24.0 parts [B] Liquid 8.6 parts [C] Liquid 8.0 parts 67% calcium carbonate aqueous dispersion 9.0 parts 48% Modified styrene / butadiene copolymer latex 6.3 parts Water 44.1 parts
（保護層の形成）
次に、下記の組成からなる保護層塗布液を前記の感熱記録層上に乾燥時の質量が２ｇ／ｍ２となるように塗布、乾燥して保護層付きの感熱記録材料を作製した。
４０％スチレン／アクリル酸エステル共重合体エマルジョン １１５部
５％ベントナイト水分散液 １７部
４５％スチレン・アクリル共重合体水性エマルジョン ４４部
３９％ステアリン酸亜鉛水分散液 １０３部
６７％炭酸カルシウム水分散液 １５部
(Formation of protective layer)
Next, a protective layer coating solution having the following composition was applied onto the heat-sensitive recording layer so that the mass upon drying was 2 g / m 2 and dried to prepare a heat-sensitive recording material with a protective layer.
40% styrene / acrylic ester copolymer emulsion 115 parts 5% bentonite aqueous dispersion 17 parts 45% styrene / acrylic copolymer aqueous emulsion 44 parts 39% zinc stearate aqueous dispersion 103 parts 67% calcium carbonate aqueous dispersion 15 copies
［実施例２］
実施例１の［Ｃ］液の式（１）の化合物を式（２）の化合物（ケミプロ化成）に代えた以外は実施例１と同様にして、本発明の感熱記録材料を作製した。
[Example 2]
A thermosensitive recording material of the present invention was produced in the same manner as in Example 1 except that the compound of formula (1) in the liquid [C] of Example 1 was replaced with the compound of formula (2) (Chemipro Chemical).
［比較例１］
実施例１の［Ｃ］液の代わりに水を加えた以外は実施例１と同様にして、比較用の感熱記録材料を作製した。
[Comparative Example 1]
A comparative heat-sensitive recording material was produced in the same manner as in Example 1 except that water was added instead of the [C] solution of Example 1.
［保存安定性試験（耐可塑剤性試験）］
ガラス板に塩化ビニルラップフィルム（可塑剤が含まれているもの）を１重に巻き付け、その上にオオクラエンジニアリング株式会社のサーマルプリンター（ＴＨ−Ｍ２／ＰＰ）を用いてパルス幅１．４ｍｓｅｃで印字（発色）した上記の実施例１、２及び比較例１で得られた感熱記録材料を張り付けた。さらに、この上に同塩化ビニルラップフィルムを１重に巻き付けた状態で、４５℃で２４時間静置した。試験前後の感熱記録材料の発色画像部のマクベス反射濃度をＧＲＥＴＡＧ−ＭＡＣＢＥＴＨ社製の測色機、商品名「ＳｐｅｃｔｒｏＥｙｅ」を用いて測定した。測色する際は、いずれも光源にイルミナントＣ、濃度基準にＡＮＳＩ Ａ、視野角２度の条件で行った。結果を下表１に示す。なお、残存率が高い程、耐可塑剤性に優れていることがわかる。残存率は以下の計算式（Ｉ）で求めた。
残存率（％）＝（試験後の感熱記録材料の発色画像部のマクベス反射濃度）/（試験前の感熱記録材料の発色画像部のマクベス反射濃度）×１００ （Ｉ）
[Storage stability test (plasticizer resistance test)]
A vinyl chloride wrap film (containing a plasticizer) is wrapped around a glass plate in a single layer and printed on it using a thermal printer (TH-M2 / PP) from Okura Engineering Co., Ltd. with a pulse width of 1.4 msec. The heat-sensitive recording materials obtained in the above-described Examples 1 and 2 and Comparative Example 1 (color development) were attached. Further, the same vinyl chloride wrap film was wound on this, and allowed to stand at 45 ° C. for 24 hours. The Macbeth reflection density of the color image portion of the heat-sensitive recording material before and after the test was measured using a colorimeter manufactured by GRETAG-MACBETH, trade name “SpectroEye”. When measuring colors, all were performed under the conditions of Illuminant C as the light source, ANSI A as the density standard, and a viewing angle of 2 degrees. The results are shown in Table 1 below. It can be seen that the higher the residual ratio, the better the plasticizer resistance. The residual rate was determined by the following calculation formula (I).
Residual rate (%) = (Macbeth reflection density of color image portion of heat-sensitive recording material after test) / (Macbeth reflection density of color image portion of heat-sensitive recording material before test) × 100 (I)
上記の表１から明らかなように、３−［（３−フェニルウレイド）フェニル］＝４−メチルベンゼンスルホナートと保存性向上剤を併用した本発明の感熱記録材料は、保存性向上剤を併用しない場合と比較して発色画像部の保存安定性に優れている事がわかる。
As apparent from Table 1 above, the heat-sensitive recording material of the present invention using 3-[(3-phenylureido) phenyl] = 4-methylbenzenesulfonate and a preservability improver together uses a preservability improver. It can be seen that the storage stability of the color image portion is excellent as compared with the case where it is not.
Claims (5)
A heat-sensitive recording paper comprising the heat-sensitive recording material or the heat-sensitive recording layer according to claim 1.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2016143363A JP2018012270A (en) | 2016-07-21 | 2016-07-21 | Heat-sensitive recording material |
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|---|---|---|---|
| JP2016143363A JP2018012270A (en) | 2016-07-21 | 2016-07-21 | Heat-sensitive recording material |
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| JP2018012270A true JP2018012270A (en) | 2018-01-25 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019130879A (en) * | 2018-02-01 | 2019-08-08 | 日本化薬株式会社 | Heat-sensitive recording material |
| JP2020040287A (en) * | 2018-09-11 | 2020-03-19 | 日本化薬株式会社 | Heat-sensitive recording material |
| JP2023001789A (en) * | 2021-06-21 | 2023-01-06 | 大阪シーリング印刷株式会社 | Thermal recording medium |
| JP7286054B1 (en) * | 2021-12-02 | 2023-06-02 | 日本化薬株式会社 | Thermal recording composition |
| WO2023100902A1 (en) * | 2021-12-02 | 2023-06-08 | 日本化薬株式会社 | Heat-sensitive recording composition |
| JP7421846B1 (en) * | 2022-08-29 | 2024-01-25 | 大阪シーリング印刷株式会社 | heat sensitive recording material |
| WO2024048447A1 (en) * | 2022-08-29 | 2024-03-07 | 大阪シーリング印刷株式会社 | Heat-sensitive recording body |
| JP7452937B1 (en) * | 2022-08-29 | 2024-03-19 | 大阪シーリング印刷株式会社 | heat sensitive recording material |
| US12427798B2 (en) | 2021-11-30 | 2025-09-30 | Nippon Kayaku Kabushiki Kaisha | Heat-sensitive recording composition |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019130879A (en) * | 2018-02-01 | 2019-08-08 | 日本化薬株式会社 | Heat-sensitive recording material |
| JP7027199B2 (en) | 2018-02-01 | 2022-03-01 | 日本化薬株式会社 | Thermal recording material |
| JP2020040287A (en) * | 2018-09-11 | 2020-03-19 | 日本化薬株式会社 | Heat-sensitive recording material |
| JP2023001789A (en) * | 2021-06-21 | 2023-01-06 | 大阪シーリング印刷株式会社 | Thermal recording medium |
| US12427798B2 (en) | 2021-11-30 | 2025-09-30 | Nippon Kayaku Kabushiki Kaisha | Heat-sensitive recording composition |
| JP7286054B1 (en) * | 2021-12-02 | 2023-06-02 | 日本化薬株式会社 | Thermal recording composition |
| WO2023100902A1 (en) * | 2021-12-02 | 2023-06-08 | 日本化薬株式会社 | Heat-sensitive recording composition |
| JP7421846B1 (en) * | 2022-08-29 | 2024-01-25 | 大阪シーリング印刷株式会社 | heat sensitive recording material |
| WO2024048447A1 (en) * | 2022-08-29 | 2024-03-07 | 大阪シーリング印刷株式会社 | Heat-sensitive recording body |
| JP7452937B1 (en) * | 2022-08-29 | 2024-03-19 | 大阪シーリング印刷株式会社 | heat sensitive recording material |
| AU2023335870B2 (en) * | 2022-08-29 | 2025-07-10 | Osaka Sealing Printing Co., Ltd. | Heat-sensitive recording medium |
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