JPH085892B2 - Fluoran compound and thermosensitive recording material containing the compound - Google Patents
Fluoran compound and thermosensitive recording material containing the compoundInfo
- Publication number
- JPH085892B2 JPH085892B2 JP2194846A JP19484690A JPH085892B2 JP H085892 B2 JPH085892 B2 JP H085892B2 JP 2194846 A JP2194846 A JP 2194846A JP 19484690 A JP19484690 A JP 19484690A JP H085892 B2 JPH085892 B2 JP H085892B2
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- compound
- formula
- paper
- recording material
- heat
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- Heat Sensitive Colour Forming Recording (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、感熱記録材料に用いられる発色性化合物と
して有用なフルオラン化合物、および該化合物を含有す
る感熱記録材料に関する。TECHNICAL FIELD The present invention relates to a fluoran compound useful as a color-forming compound used in a heat-sensitive recording material, and a heat-sensitive recording material containing the compound.
従来、無色ないし淡色の電子供与性化合物(発色性化
合物)と有機もしくは無機の電子受容性物質(顕色剤)
との呈色反応を利用した感熱記録が広く普及している。Conventionally, colorless or light-colored electron-donating compounds (color-forming compounds) and organic or inorganic electron-accepting substances (developers)
Thermal recording using the color reaction with is widely used.
この記録方式には、発色性化合物として、フルオラン
化合物が広く用いられている。In this recording method, a fluoran compound is widely used as a color forming compound.
従来、フルオラン化合物として、例えば、式(A)〜
式(F)、 の化合物が知られている。Conventionally, as a fluoran compound, for example, formula (A) ~
Formula (F), The compound of is known.
しかし、式(A)の化合物は、感熱記録材料に使用す
る際に、顕色剤、例えばビスフェノールAとの混合物
は、それ自体灰色ないし黒灰色に発色し、これを紙に塗
布すると、灰色ないし黒灰色に着色(地汚れ)した紙し
か得られないという欠点があった。However, when the compound of the formula (A) is used in a heat-sensitive recording material, a mixture with a developer, for example, bisphenol A, develops a gray color or a black gray color by itself, and when it is applied to paper, it is gray or black. It has the drawback that only black-gray colored (ground stain) paper can be obtained.
また、式(B)〜式(F)の化合物は、塗布した直後
は比較的白色度の高い紙が得られるものの、湿度、光ま
たは熱により灰色ないし褐色に変色するという欠点があ
った。Further, the compounds of the formulas (B) to (F) have a drawback that they are discolored to gray or brown due to humidity, light or heat, although a paper having a relatively high whiteness can be obtained immediately after coating.
最近、感熱記録材料は、ファクシミリ等のように室内
で利用される以外にも、例えば、テレホンカード等に代
表されるプリペイドカードのように室外やより過酷な条
件下で使用されるようになつてきた。そのため、感熱記
録材料にはより一層の保存安定性が求められている。Recently, thermal recording materials have been used not only indoors such as facsimiles but also outdoors and under more severe conditions such as prepaid cards typified by telephone cards and the like. It was Therefore, the thermal recording material is required to have further storage stability.
本発明の課題は、感熱記録材料用の発色性化合物とし
て、保存安定性の優れた新規なフルオラン化合物を提供
することであり、併せてこの化合物の製造方法およびこ
の化合物を含有する感熱記録材料を提供することであ
る。An object of the present invention is to provide a novel fluorane compound having excellent storage stability as a color-forming compound for a heat-sensitive recording material, and also to provide a method for producing this compound and a heat-sensitive recording material containing this compound. Is to provide.
本発明者等は、上述の課題を解決するために種々の化
合物を探索し、本発明に到達した。The present inventors have arrived at the present invention by searching various compounds in order to solve the above problems.
すなわち、本発明は、式(I)で表されるフルオラン
化合物であり、 この化合物を、式(II) で表される安息香酸誘導体と一般式(III) (式中、Rは低級アルキル基を示す)で、表されるジフ
ェニルアミン誘導体とを反応させて製造する方法、およ
びこのフルオラン化合物を含有することを特徴とする感
熱記録材料である。That is, the present invention is a fluoran compound represented by the formula (I), This compound has the formula (II) A benzoic acid derivative represented by the general formula (III) (Wherein R represents a lower alkyl group) and a diphenylamine derivative represented by the reaction, and a heat-sensitive recording material containing the fluorane compound.
本発明の式(I)のフルオラン化合物を製造するのに
用いられる式(II)の安息香酸誘導体は、代表的には、
3−N−シクロヘキシル−N−n−プロピルアミノフェ
ノールと無水フタル酸とを無溶媒、あるいはベンゼン、
トルエン、キシレンまたはテトラクロルエチレン等の溶
媒中で反応させて製造できる。またこの反応の際、例え
ば、塩化亜鉛のごときルイス酸を添加してもよい。The benzoic acid derivative of formula (II) used to prepare the fluorane compound of formula (I) of the present invention is typically
3-N-cyclohexyl-N-n-propylaminophenol and phthalic anhydride without solvent, or benzene,
It can be produced by reacting in a solvent such as toluene, xylene or tetrachloroethylene. During this reaction, a Lewis acid such as zinc chloride may be added.
また、一般式(III)で表されるジフェニルアミン誘
導体は、一般式(III)において、Rは低級アルキル基
を示し、低級アルキル基の具体例としてはメチル基また
はエチル基を好ましい例として挙げることができる。特
にメチル基を好ましいものとしてあげることができる。Further, in the diphenylamine derivative represented by the general formula (III), in the general formula (III), R represents a lower alkyl group, and a specific example of the lower alkyl group is a methyl group or an ethyl group. it can. A methyl group is particularly preferable.
式(I)のフルオラン化合物は、式(II)の安息香酸
誘導体と一般式(III)のジフェニルアミン誘導体を、
例えば、濃硫酸、発煙硫酸を添加した濃硫酸、ポリリン
酸、五酸化リン、無水塩化アルミニウム等の脱水縮合剤
の存在下、より好ましくは濃硫酸中で反応後、アルカリ
性として好適に製造できる。脱水縮合の反応は0〜100
℃の反応温度が好ましく、特に濃硫酸中で反応を行う場
合、0〜50℃の温度が特に好ましい。反応時間は反応温
度に大きく左右されるが、通常、数時間ないし100時間
で行うのが好ましい。また脱水縮合後、通常アルカリ処
理を行うが、アルカリ処理を行う場合においては、水酸
化カリウム、水酸化ナトリウム水等により、pHを9〜12
にし、0〜100℃の温度範囲で行うのが好ましい。この
際、水以外の溶媒として、ベンゼン、トルエン等の溶媒
の共存下にアルカリ処理を行ってもよい。The fluoran compound of the formula (I) is a benzoic acid derivative of the formula (II) and a diphenylamine derivative of the general formula (III),
For example, it can be suitably produced as alkaline after reacting in the presence of a dehydrating condensing agent such as concentrated sulfuric acid, concentrated sulfuric acid added with fuming sulfuric acid, polyphosphoric acid, phosphorus pentoxide, or anhydrous aluminum chloride, more preferably in concentrated sulfuric acid. Dehydration condensation reaction is 0-100
A reaction temperature of 0 ° C is preferred, especially when the reaction is carried out in concentrated sulfuric acid, a temperature of 0 to 50 ° C is particularly preferred. The reaction time largely depends on the reaction temperature, but it is usually preferably several hours to 100 hours. After dehydration condensation, alkali treatment is usually carried out, but when alkali treatment is carried out, the pH is adjusted to 9 to 12 with potassium hydroxide, aqueous sodium hydroxide or the like.
The temperature is preferably 0 to 100 ° C. At this time, the alkali treatment may be performed in the coexistence of a solvent other than water, such as benzene or toluene.
本発明のフルオラン化合物を感熱記録材料に用いるに
は、式(I)のフルオラン化合物と顕色剤(例えば、ビ
スフェノールAまたはそのハロゲン化物、アルキル化
物、ジヒドロキシジフェニルスルホンまたはそのハロゲ
ン化物、アルキル化ヒドロキシ安息香酸エステル類、ハ
イドロキノンモノエーテル類のようなフェノール類、サ
リチル酸誘導体、サリチル酸アミド誘導体、尿素誘導
体、チオ尿素誘導体のような有機顕色剤、酸性白土、ア
タパルガイト、活性白土、塩化アルミニウム、臭化亜鉛
のような無機顕色剤)の微細水分散液に結着剤(例え
ば、ポリビニルアルコールまたはその変性物、メチルセ
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、アラビアゴム、スチレン−無水マレイ
ン酸共重合物の塩、イソブチレン−アクリル酸−無水マ
レイン酸の共重合物など)、顔料(タルク、カオリン、
炭酸カルシウム等)、更に、必要に応じ、増感剤(高級
脂肪酸アミド類、芳香族カルボン酸またはスルホン酸の
エステル類、芳香族ないし芳香族基置換脂肪族エーテル
類または芳香族ないし芳香族基置換脂肪族炭化水素等一
般に公知の感熱記録材用増感剤)、その他の添加剤(例
えば、紫外線吸収剤、消泡剤等)を加え、微細分散液と
し、適当な支持体(例えば、紙、プラスチックシート、
樹脂被膜された紙等)上に塗布し、感熱記録材料として
使用することができる。勿論、水分散系でなく、溶剤を
使用する系においても問題なく使用できる。In order to use the fluorane compound of the present invention in a heat-sensitive recording material, a fluorane compound of the formula (I) and a developer (for example, bisphenol A or a halide thereof, an alkylated product, dihydroxydiphenyl sulfone or a halide thereof, an alkylated hydroxybenzoic acid) are used. Acid esters, phenols such as hydroquinone monoethers, salicylic acid derivatives, salicylic acid amide derivatives, urea derivatives, organic developers such as thiourea derivatives, acid clay, attapulgite, activated clay, aluminum chloride, zinc bromide Binder (for example, polyvinyl alcohol or a modified product thereof, methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, gum arabic, styrene-maleic anhydride copolymer salt, isobutene) in a fine aqueous dispersion of such an inorganic developer. Len - acrylic acid - such as a copolymer of maleic acid), pigment (talc, kaolin,
Calcium carbonate, etc., and if necessary, sensitizers (higher fatty acid amides, esters of aromatic carboxylic acids or sulfonic acids, aromatic or aromatic group-substituted aliphatic ethers or aromatic or aromatic group-substituted) Generally known sensitizers for heat-sensitive recording materials such as aliphatic hydrocarbons) and other additives (for example, ultraviolet absorbers, defoaming agents, etc.) are added to form a fine dispersion, and a suitable support (for example, paper, Plastic sheet,
It can be used as a heat-sensitive recording material by coating it on resin-coated paper or the like. Of course, it can be used without problems in a system using a solvent instead of an aqueous dispersion system.
発色性化合物として式(I)の化合物は単独で用いる
こともでき、さらには、例えば発色の色などの調整のた
めに、他の発色性化合物、例えば、トリフェニルメタン
ラクトン類、フルオラン類、スピロピラン類を所望に応
じて混合して用いることもできる。The compound of formula (I) can be used alone as the color forming compound, and further, for adjusting the color of the color forming, for example, other color forming compounds such as triphenylmethane lactones, fluoranes and spiropyran. It is also possible to mix and use the classes as desired.
本発明の式(I)のフルオラン化合物の融点は257〜2
58℃であり、例えば公知の式(A)の化合物の融点が19
5〜198℃、式(B)の化合物の融点が195〜197℃、また
式(C)の化合物の融点が124〜126℃であるのに比較し
て非常に高い。The melting point of the fluoran compound of formula (I) of the present invention is 257-2.
58 ° C., for example, the melting point of the known compound of formula (A) is 19
5 to 198 ° C., the melting point of the compound of formula (B) is 195 to 197 ° C., and the melting point of the compound of formula (C) is 124 to 126 ° C., which are extremely high.
また、本発明の化合物は、各種有機溶剤(例えば、ベ
ンゼン、トルエンのような炭化水素系溶剤や酢酸エチル
のようなエステル類、アセトンのようなケトン類)に対
し非常に溶解度が低い。例えばトルエンに対する溶解度
を式(A)〜式(F)の化合物と比較した結果は第1表
に示す通りである。Further, the compound of the present invention has extremely low solubility in various organic solvents (for example, hydrocarbon solvents such as benzene and toluene, esters such as ethyl acetate, ketones such as acetone). For example, the results of comparing the solubility in toluene with the compounds of formulas (A) to (F) are shown in Table 1.
溶解度は25℃におけるトルエンに対する重量%で示し
た。The solubilities are shown in% by weight with respect to toluene at 25 ° C.
上述のような性質を有する本発明の化合物を感熱記録
材料に使用すると地汚れのない白色度の高い感熱紙が得
られ、その紙の保存安定性(例えば耐湿熱性、耐溶剤
性)は非常に優れている。例えば、顕色剤としてビスフ
ェールAを使用し発色性化合物として本発明の式(I)
の化合物を用いた感熱紙と式(A)〜式(F)のいずれ
かの化合物を用いた感熱記録紙の地肌(未発色部分)の
耐湿熱性および耐油性を比較した結果は第2表に示す通
りである。 When the compound of the present invention having the above-mentioned properties is used in a heat-sensitive recording material, a heat-sensitive paper having high whiteness and free from background stain is obtained, and the storage stability (for example, moist heat resistance and solvent resistance) of the paper is very high. Are better. For example, Bisfer A is used as a color developer and the compound of formula (I) of the present invention is used as a color-forming compound.
Table 2 shows the results of a comparison between the heat-sensitive paper using the compound of Example 1 and the heat-sensitive recording paper using any of the compounds of the formulas (A) to (F) for the moist heat resistance and oil resistance of the background (uncolored portion). As shown.
尚、耐湿熱試験は、各化合物を用いて作成した感熱紙
を60℃で90%の相対湿度中24時間保持し、目視により紙
の汚れを観察した。In the moist heat resistance test, the thermal paper prepared by using each compound was kept at 60 ° C. in 90% relative humidity for 24 hours, and the stain of the paper was visually observed.
また、耐油性試験は、感熱紙をフタル酸ジオクチルエ
ステルと接触させ1週間放置した後、目視により紙のよ
ごれを観察した。In the oil resistance test, the thermal paper was brought into contact with dioctyl phthalate and left for 1 week, and then the paper was visually observed for dirt.
を表す。 Represents
本発明の式(I)のフルオラン化合物は、式(A)〜
式(F)のフルオラン化合物とはフルオラン構造におい
て3位のアミノ基上の置換基のみが異なる構造であり、
特に式(B)のフルオラン化合物とはアミノ基上の一方
のメチル基をn−プロピル基に変換した構造上の違いの
みで、上述したように式(A)、式(B)や式(C)の
フルオラン化合物に比べ融点が非常に高く、また式
(A)〜式(F)のフルオラン化合物に比べ有機溶剤に
対する溶解度が非常に低い。このような性質を有する本
発明の式(I)のフルオラン化合物を感熱記録材料に用
いるとその感熱紙の保存安定性が大きく向上する。The fluoran compound of the formula (I) of the present invention has the formula (A) to
The fluorane compound of the formula (F) is a structure different from the fluorane structure only in the substituent on the amino group at the 3-position,
In particular, it differs from the fluorane compound of the formula (B) only in the structure in which one methyl group on the amino group is converted into an n-propyl group, and as described above, the formula (A), the formula (B) and the formula (C 2) has a much higher melting point than that of the fluorane compound, and has a much lower solubility in an organic solvent than the fluorane compound of the formulas (A) to (F). When the fluorane compound of the formula (I) of the present invention having such properties is used in a heat-sensitive recording material, the storage stability of the heat-sensitive paper is greatly improved.
特に、有機溶剤に対する溶解度に関しては、通常、例
えば、メチル基をn−プロピル基に変換するように、よ
り長鎖のアルキル基に変換すると、有機溶剤、特に炭化
水素系溶剤に対しては溶解度が高くなると考えられてい
る。しかし、本発明の式(I)のフルオラン化合物と式
(A)のフルオラン化合物のトルエンに対する溶解度を
比較すると式(I)のフルオラン化合物の方が式(A)
のフルオラン化合物よりも溶解度が非常に低いことは、
驚くべきことである。In particular, regarding the solubility in an organic solvent, generally, for example, when a methyl group is converted into a longer-chain alkyl group such as an n-propyl group, the solubility in an organic solvent, particularly a hydrocarbon solvent is increased. It is believed to be higher. However, comparing the solubilities of the fluorane compound of formula (I) and the fluorane compound of formula (A) of the present invention in toluene, the fluorane compound of formula (I) has the formula (A)
The solubility is much lower than that of
It's amazing.
とくに有機溶剤に対する溶解度に関しては、例えば、
式(B)の化合物のアミノ基上のメチル基をイソアミル
基に変えた式(E)の化合物 のように、より長鎖のアルキル基を導入すると有機溶
剤、とくに炭化水素系溶剤(例えば、トルエン)に対し
ては溶解度が高くなることが知られている(例えば、特
開昭54-34909号公報)。Especially regarding the solubility in organic solvents, for example,
A compound of formula (E) in which the methyl group on the amino group of the compound of formula (B) is changed to an isoamyl group As described above, introduction of a longer-chain alkyl group is known to increase the solubility in an organic solvent, particularly a hydrocarbon solvent (for example, toluene) (for example, JP-A-54-34909). Gazette).
しかし、アミノ基上にn−プロピル基を有する本発明
の式(I)のフルオラン化合物は、式(B)、式(C)
や式(D)のフルオラン化合物に比べてトルエンに対す
る溶解度が非常に低いという従来見出されていなかった
特徴を有し、これを発色性化合物として用い保存安定性
に優れた感熱記録紙を提供できる。However, the fluorane compound of the formula (I) of the present invention having an n-propyl group on the amino group has the formula (B) and the formula (C).
And a fluoran compound of the formula (D), which has a feature that has not been found in the past that the solubility in toluene is extremely low, can be used as a color forming compound to provide a thermal recording paper having excellent storage stability. .
以下、実施例により、本発明を更に具体的に説明する
が、本発明はこれらの実施例に限定されるものではな
い。Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
実施例1 〔式(I)の化合物の製造〕 2−(4′−N−シクロヘキシル−N−n−プロピル
アミノ−2′−ヒドロキシベンゾイル)安息香酸〔式
(II)の化合物〕20gを100mlの濃硫酸に10℃で溶解後、
4−メトキシ−2−メチルジフェニルアミン〔一般式
(III)においてRがメチル基の化合物〕11gを同温度で
加え、10〜25℃で48時間攪拌した。反応混合物を600ml
の氷水に排出し、析出した固体を集め水洗後その固体を
10%NaOH水(500ml)中に加え60〜70℃で2時間攪拌し
た。固体を濾過、水洗後、イソプロパノール100mlで洗
浄した。Example 1 [Preparation of compound of formula (I)] 2- (4'-N-cyclohexyl-Nn-propylamino-2'-hydroxybenzoyl) benzoic acid [compound of formula (II)] 20 g of 100 ml After dissolving in concentrated sulfuric acid at 10 ℃,
11 g of 4-methoxy-2-methyldiphenylamine (a compound in which R is a methyl group in the general formula (III)) was added at the same temperature, and the mixture was stirred at 10 to 25 ° C. for 48 hours. 600 ml of reaction mixture
The solid that has precipitated is collected and washed with water, and then the solid is collected.
The mixture was added to 10% NaOH water (500 ml) and stirred at 60 to 70 ° C for 2 hours. The solid was filtered, washed with water, and then washed with 100 ml of isopropanol.
さらに、トルエンで2回洗浄し、目的とする3−N−
シクロヘキシル−N−n−プロピルアミノ−6−メチル
−7−アニリノフルオラン20g(収率69%)をほとんど
無色の結晶として得た。Furthermore, it is washed twice with toluene to obtain the desired 3-N-
20 g (69% yield) of cyclohexyl-Nn-propylamino-6-methyl-7-anilinofluorane was obtained as almost colorless crystals.
融点257〜258℃。この化合物の赤外吸収スペクトル
(KBr錠剤)は第1図に示した。また粉末X線回折図を
第2図に示した。Melting point 257-258 ° C. The infrared absorption spectrum (KBr tablet) of this compound is shown in FIG. The powder X-ray diffraction pattern is shown in FIG.
実施例2 〔式(I)の化合物を用いた感熱記録紙の作成〕 実施例1で製造した本発明の3−N−シクロヘキシル
−N−n−プロピルアミノ−6−メチル−7−アニリノ
フルオラン10g、10%ポリビニールアルコール水溶液5g
及び水37.5gの混合物をサンドミルで粒径3μに微粒化
した。一方、ビスフェノールAを同様に分散し38%の顕
色剤分散液を得た。この顕色剤分散液65.8g、上記の3
−N−シクロヘキシル−N−n−プロピルアミノ−6−
メチル−7−アニリノフルオランの水分散液50g、60%
軽質炭化カルシウム水分散液18.3g、100%ポリビニール
アルコール水溶液88gおよび水51.9gを混合した。Example 2 [Preparation of thermal recording paper using compound of formula (I)] 3-N-cyclohexyl-Nn-propylamino-6-methyl-7-anilinoflu of the present invention prepared in Example 1 Oran 10g, 10% polyvinyl alcohol aqueous solution 5g
A mixture of water and 37.5 g of water was atomized with a sand mill to a particle size of 3 μ. On the other hand, bisphenol A was similarly dispersed to obtain a 38% developer dispersion. 65.8 g of this color developer dispersion, the above 3
-N-cyclohexyl-N-n-propylamino-6-
Aqueous dispersion of methyl-7-anilinofluorane 50g, 60%
18.3 g of an aqueous dispersion of light calcium carbide, 88 g of a 100% polyvinyl alcohol aqueous solution and 51.9 g of water were mixed.
この混合液を白色原紙にワイヤーロッドNo.10を用い
塗布後、室温で風乾し地汚れのない非常に白い感熱記録
紙を得た。この感熱記録紙は、加熱により極めて迅速に
わずかに赤味を帯びた黒色に発色した。This mixed solution was applied to a white base paper using a wire rod No. 10 and then air-dried at room temperature to obtain a very white thermosensitive recording paper free of background stain. The heat-sensitive recording paper developed a slightly reddish black color very quickly when heated.
この発色像の保存安定性(耐熱性、耐湿熱性、耐光性
等)は良好であった。The storage stability (heat resistance, wet heat resistance, light resistance, etc.) of this color image was good.
また、この感熱記録紙を60℃、90%相対湿度中、24間
保存したところ、紙は塗布直後の白色度を保ち、地汚れ
はまったく認められなかった。また、紙の表面をフタル
酸ジオクチルと接触させた後、1週間保存したところ、
紙の地汚れはまったく認められなかった(第2表)。When this thermosensitive recording paper was stored for 24 hours at 60 ° C and 90% relative humidity, the paper retained its whiteness immediately after coating and no scumming was observed. Also, after contacting the surface of the paper with dioctyl phthalate and storing it for 1 week,
No background stain on the paper was observed (Table 2).
比較例 実施例2において、3−N−シクロヘキシル−N−n
−プロピルアミノ−6−メチル−7−アニリノフルオラ
ンの代わりに3−N−エチル−N−エチルアミノ−6−
メチル−7−アニリノフルオラン〔式(A)の化合物、
3−N−ヘキシル−N−メチルアミノ−6−メチル−7
−アニリノフルオラン〔式(B)の化合物〕、3−N−
ヘキシル−N−エチルアミノ−6−メチル−7−アニリ
ノフルオラン〔式(C)の化合物〕、3−N−ヘキシル
−N−i−ブチルアミノ−6−メチル−7−アニリノフ
ルオラン〔式(D)の化合物〕、3−N−ヘキシル−N
−i−ヘプチルアミノ−6−メチル−7−アニリノフル
オラン〔式(E)の化合物〕または3−N−ヘキシル−
N−n−オクチルアミノ−6−メチル−7−アニリノフ
ルオラン〔式(F)の化合物〕を用い、それぞれ実施例
2に記載した方法に従い感熱記録紙を作り、耐湿熱試験
および耐油試験を行った。結果は第2表に示した。Comparative Example In Example 2, 3-N-cyclohexyl-N-n
3-N-ethyl-N-ethylamino-6- instead of -propylamino-6-methyl-7-anilinofluorane
Methyl-7-anilinofluorane [compound of formula (A),
3-N-hexyl-N-methylamino-6-methyl-7
-Anilinofluorane [compound of formula (B)], 3-N-
Hexyl-N-ethylamino-6-methyl-7-anilinofluorane [compound of formula (C)], 3-N-hexyl-N-i-butylamino-6-methyl-7-anilinofluorane [ Compound of formula (D)], 3-N-hexyl-N
-I-heptylamino-6-methyl-7-anilinofluorane [compound of formula (E)] or 3-N-hexyl-
Using Nn-octylamino-6-methyl-7-anilinofluorane [compound of formula (F)], a heat-sensitive recording paper was prepared according to the method described in Example 2, and a moisture-heat resistance test and an oil resistance test were conducted. went. The results are shown in Table 2.
なお、式(A)の化合物を用いた感熱記録紙の塗布面
は塗布直後すでに少し灰色に地汚れしていた。The coated surface of the thermal recording paper using the compound of formula (A) was already slightly soiled in gray immediately after coating.
第1図は式(I)のフルオラン化合物の赤外吸収スペク
トル(KBr錠)を示した。 縦軸は透過率を表し、横軸は波数(cm-1)を表す。 第2図は式(I)のフルオラン化合物の粉末X線回折図
を示した。縦軸は回折強度を表し、横軸は回折角(2
θ)を表す。FIG. 1 shows the infrared absorption spectrum (KBr tablets) of the fluoran compound of formula (I). The vertical axis represents the transmittance, and the horizontal axis represents the wave number (cm -1 ). FIG. 2 shows the powder X-ray diffraction pattern of the fluoran compound of formula (I). The vertical axis represents the diffraction intensity, and the horizontal axis represents the diffraction angle (2
θ).
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭49−109120(JP,A) 特開 昭58−89395(JP,A) 特開 昭61−195891(JP,A) ─────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-49-109120 (JP, A) JP-A-58-89395 (JP, A) JP-A-61-195891 (JP, A)
Claims (2)
ルオラン化合物を含有することを特徴とする感熱記録材
料。2. A heat-sensitive recording material containing a fluorane compound represented by the formula (I) according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2194846A JPH085892B2 (en) | 1989-08-01 | 1990-07-25 | Fluoran compound and thermosensitive recording material containing the compound |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1-197948 | 1989-08-01 | ||
JP19794889 | 1989-08-01 | ||
JP2194846A JPH085892B2 (en) | 1989-08-01 | 1990-07-25 | Fluoran compound and thermosensitive recording material containing the compound |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH03169883A JPH03169883A (en) | 1991-07-23 |
JPH085892B2 true JPH085892B2 (en) | 1996-01-24 |
Family
ID=26508771
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2194846A Expired - Fee Related JPH085892B2 (en) | 1989-08-01 | 1990-07-25 | Fluoran compound and thermosensitive recording material containing the compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH085892B2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011108994A (en) | 2009-11-20 | 2011-06-02 | Elpida Memory Inc | Semiconductor device |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5123204B2 (en) * | 1972-11-21 | 1976-07-15 | ||
JPS5889395A (en) * | 1981-11-20 | 1983-05-27 | Ricoh Co Ltd | Heat-sensitive recording medium |
JPS61195891A (en) * | 1985-02-22 | 1986-08-30 | グラフイツク コントロールス コーポレーシヨン | Composition for heat developing printing |
-
1990
- 1990-07-25 JP JP2194846A patent/JPH085892B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPH03169883A (en) | 1991-07-23 |
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