JPH0153976B2 - - Google Patents
Info
- Publication number
- JPH0153976B2 JPH0153976B2 JP59042829A JP4282984A JPH0153976B2 JP H0153976 B2 JPH0153976 B2 JP H0153976B2 JP 59042829 A JP59042829 A JP 59042829A JP 4282984 A JP4282984 A JP 4282984A JP H0153976 B2 JPH0153976 B2 JP H0153976B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- substituted
- parts
- recording liquid
- 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.)
- Expired
Links
- 239000007788 liquid Substances 0.000 claims description 22
- -1 N-methylanilino group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000009833 condensation Methods 0.000 description 12
- 230000005494 condensation Effects 0.000 description 12
- 239000000975 dye Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000047703 Nonion Species 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Description
本発明はモノアゾ化合物及びそれを含有した水
性記録液に関する。更に詳しくは遊離酸として式
（Ｉ）
〔式（Ｉ）においてR1、R2は各々独立にカルボ
キシル基、スルホン酸基、スルホンアミド基、メ
チル基又は塩素原子で置換されていてもよいアニ
リノ基；Ｎ−メチルアニリノ基；スルホン酸基又
はメチル基で置換されていてもよいフエノキシ
基；炭素数４以内のアルキル基又はアルカノール
基で置換されていてもよいアミノ基；モルホリノ
基；メトキシ基又はエトキシを表わす。又ｎは１
又は２を表わす。〕
で表わされるモノアゾ化合物及びそれを含有する
水性記録液に関する。
従来、筆記用、スタンプ用、ジエツトインク用
等に使用される水性記録液用色素としては、直接
染料、酸性染料、塩基性染料が用いられている。
しかしながら印字、印刷又は筆記された文字の耐
光・耐水性、更には記録液調製用溶剤との相溶性
等水性記録液用色素に要求される諸性質の全てを
満足する染料は極めて少ない。
特に赤色系色素について考えてみると、それら
のうちキノン系染料は耐光・耐水性は良いが溶剤
に対する溶解度が不十分であり、またアゾ系染料
は溶剤のうちの水に対する溶解度はよいが耐光
性、有機溶剤との相溶性が悪いというような長
所、短所を有しており、水性記録液用色素として
満足な結果を与えるものは少ない。
そこで本発明者らは水性記録液用色素（染料）
として要求される諸性質を兼ね備えた赤色染料を
製出すべく鋭意研究を行つた結果前記式（Ｉ）で
表わされるモノアゾ化合物がこれを水性記録液と
して使用した場合、耐水性、溶剤との相溶性はも
とより耐光性においても充分満足しうるものであ
ることを見い出し本発明を完成させた。
本発明の前記式（Ｉ）で表わされるモノアゾ化
合物は例えば遊離酸として式（）
（式中ｎは前記式（Ｉ）におけると同じ意味を表
わす。）
で表わされる化合物と次式（）及び（）
R1−Ｈ （）
R2−Ｈ （）
〔式（）及び（）においてはR1、R2は前記
と同じ意味を表わす。〕
で表わされる化合物を任意の順序で水媒質中で縮
合させる（２次縮合及び３次縮合）か、遊離酸と
して式（Ｖ）
〔式（Ｖ）においてｎは前記と同じ意味を表わ
す〕
で表わされる化合物と水媒質中で式（）
（式（）においてR1は前記と同じ意味を表わ
す）
で表わされる化合物と縮合し（２次縮合）、次い
で式（）で表わされる化合物と縮合する（３次
縮合）か、式（Ｖ）で表わされる化合物と式
（）
〔式（）においてR1、R2は前記と同じ意味を
表わす〕
で表わされる化合物とを水媒質中で縮合する（３
次縮合）ことによつてえられる。
前記製法において２次縮合はPH３〜10、温度15
〜60℃より好ましくはPH５〜８、温度20〜40℃
で、又３次縮合はPH４〜11、温度40〜90℃より好
ましくはPH5.5〜10温度50〜80℃で行われる。又
式（）、（）で表わされる化合物の具体的な例
としては次のものが挙げられる。
The present invention relates to a monoazo compound and an aqueous recording liquid containing the same. More specifically, as the free acid, the formula (I) [In formula (I), R 1 and R 2 are each independently an anilino group which may be substituted with a carboxyl group, a sulfonic acid group, a sulfonamide group, a methyl group or a chlorine atom; an N-methylanilino group; a sulfonic acid group, or It represents a phenoxy group which may be substituted with a methyl group; an amino group which may be substituted with an alkyl group or an alkanol group having up to 4 carbon atoms; a morpholino group; a methoxy group or ethoxy. Also, n is 1
or 2. ] The present invention relates to a monoazo compound represented by the following and an aqueous recording liquid containing the same. Conventionally, direct dyes, acid dyes, and basic dyes have been used as dyes for aqueous recording liquids used for writing, stamps, jet inks, and the like.
However, there are very few dyes that satisfy all of the properties required of dyes for aqueous recording liquids, such as light resistance and water resistance of printed or written characters, and further compatibility with solvents for preparing recording liquids. Considering red pigments in particular, quinone dyes have good light and water resistance but insufficient solubility in solvents, and azo dyes have good solubility in water, but have poor light resistance. However, they have advantages and disadvantages such as poor compatibility with organic solvents, and there are few dyes that give satisfactory results as dyes for aqueous recording liquids. Therefore, the present inventors developed a pigment (dye) for aqueous recording liquid.
As a result of extensive research in order to produce a red dye that has the properties required as The present invention was completed based on the discovery that the light resistance as well as light resistance was sufficiently satisfactory. The monoazo compound represented by the above formula (I) of the present invention is, for example, a free acid of the formula (I). (In the formula, n represents the same meaning as in the above formula (I).) Compounds represented by the following formulas () and () R 1 -H () R 2 -H () R 1 and R 2 have the same meanings as above. ] The compound represented by formula (V) is condensed in an arbitrary order in an aqueous medium (secondary condensation and tertiary condensation) or as a free acid of formula (V). [In formula (V), n represents the same meaning as above] In a compound represented by the formula () and an aqueous medium, (In formula (), R 1 represents the same meaning as above) (secondary condensation), and then condensation with a compound represented by formula () (tertiary condensation), or formula (V) Compounds and formulas represented by () [In formula (), R 1 and R 2 have the same meanings as above] is condensed in an aqueous medium (3
(condensation). In the above manufacturing method, the secondary condensation is performed at a pH of 3 to 10 and a temperature of 15
~60℃, preferably PH5~8, temperature 20~40℃
The tertiary condensation is carried out at a pH of 4 to 11 and a temperature of 40 to 90°C, more preferably at a pH of 5.5 to 11 and a temperature of 50 to 80°C. Further, specific examples of compounds represented by formulas () and () include the following.
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】
NH3、CH3NH2、C2H5NH2、C4H9NH2、
（CH3）2NH、（C2H5）2NH、（C3H7）2NH、
NH2C2H4OH、NH（C2H4OH）2、
[Formula] NH 3 , CH 3 NH 2 , C 2 H 5 NH 2 , C 4 H 9 NH 2 ,
( CH3 ) 2NH , ( C2H5 ) 2NH , ( C3H7 ) 2NH ,
NH2C2H4OH , NH ( C2H4OH ) 2 ,
【式】【formula】
【式】【formula】
【式】CH3OH、C2H5OH
式（Ｉ）で表わされる化合物は縮合反応が終了し
たのち反応液を酸析して遊離酸の形で、又常法に
よつて反応液中でリチウム塩、ナトリウム塩、カ
リウム塩、アンモニウム塩、脂肪族アミン塩等に
代え、必要に応じて塩析を行つてから別するこ
とによつてえることが出来る。水性記録液調製の
為には遊離酸であつてもその塩であつても全く同
じような効果を与える。
本発明のモノアゾ化合物は公知方法に従い水、
有機溶剤、界面活性剤等と共に混和して水性記録
液とすることが出来る。水性記録液調製に用いる
有機溶剤としては水と相溶性があり、スルホン基
含有のアゾ化合物に対する溶解力がたかく、かつ
適度の吸湿性を有するものが好ましく例えばエチ
レングリコール、ジエチレングリコール、トリエ
チレングリコール、テトラエチレングリコール等
のグリコール類、メチルセロソルブ、エチルセロ
ソルブ等のセロソルブ類、メチルカルビトール、
エチルカルビトール等のカルビトール類、ジエタ
ノールアミン、トリエタノールアミン等のアルカ
ノールアミン類等が用いられる。そして本発明の
モノアゾ化合物0.5〜30重量％、溶剤２〜50重量
％、水40〜90重量％を含有するように記録液を調
製するのが望ましい。更に水性記録液の溶解安定
性を良くする目的で、アニオン系又はノニオン系
界面活性剤を水性記録液に対し0.1〜２重量％用
いてもよい。
本発明のモノアゾ化合物を用いて調製された水
性記録液は筆記、スタンプ、インクジエツト等に
用いられ堅牢度のすぐれた赤色系の筆記体、印
字、印刷物を与える。
以下実施例により本発明を具体的に説明する
が、本発明はその要旨を超えない限りこれらの実
施例に限定されるものではない。なお、実施例に
おいてカルボキシル基、スルホン酸基は遊離の形
で表わすものとする。
実施例 １
式
で示される化合物43重量部（以下部とは重量部を
示す）を水400部に溶解させ、15〜45℃、PH2.0〜
6.0 ３時間でアニリン4.6部と縮合し、（２次縮
合）更にモノエタノールアミン3.6部を加え、温
度を65℃に保ち、PH9.0〜10.5で３時間縮合反応
を行つた（３次縮合）。この反応液に塩酸25部を
加え、固形分を別、乾燥して45部の下記式で示
されるモノアゾ化合物を得た。
λmax545nm（純水中で測定、以下同じ）
実施例 ２
実施例１で得られたモノアゾ化合物 ５部
ジエチレングリコール 10部
トリエチレングリコール ５部
プロピレングリコール 10部
ノイゲンＰ（第一工業製薬(株)製、ノニオン系界
面活性剤） 0.2部
水 69.8部
を混合、撹拌した後、工業用紙で過し水性記
録液を得た。次いでシヤープ製IO−700（インク
ジエツト式カラープリンター）を用いてこの記録
液による印刷物を作成しカーボンフエードメータ
ーで印刷物の耐光性を測定した。すぐれた耐光堅
牢度を示し、又この印刷物は耐水性についてもす
ぐれた結果を与えた。
実施例 ４〜20
実施例１に準じた方法で次の表の化合物を製造
した。表には構造式とそのλmaxを示した。又こ
れらの化合物を用いて実施例２と同様にして水性
記録液を調製し前記カラープリンターにより印刷
し赤色系の印刷物をえた。[Formula] CH 3 OH, C 2 H 5 OH After the condensation reaction is completed, the compound represented by formula (I) can be acid-precipitated from the reaction solution in the form of a free acid, or in the reaction solution by a conventional method. Instead of using lithium salts, sodium salts, potassium salts, ammonium salts, aliphatic amine salts, etc., it can be obtained by salting out if necessary and then separating. For the preparation of aqueous recording liquids, both free acids and their salts have exactly the same effect. The monoazo compound of the present invention can be prepared using water,
It can be mixed with an organic solvent, a surfactant, etc. to form an aqueous recording liquid. The organic solvent used for preparing the aqueous recording liquid is preferably one that is compatible with water, has a strong dissolving power for sulfonic group-containing azo compounds, and has an appropriate hygroscopicity, such as ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, etc. Glycols such as ethylene glycol, cellosolves such as methyl cellosolve and ethyl cellosolve, methyl carbitol,
Carbitols such as ethyl carbitol, alkanolamines such as diethanolamine, triethanolamine, etc. are used. The recording liquid is preferably prepared to contain 0.5 to 30% by weight of the monoazo compound of the present invention, 2 to 50% by weight of the solvent, and 40 to 90% by weight of water. Furthermore, for the purpose of improving the dissolution stability of the aqueous recording liquid, an anionic or nonionic surfactant may be used in an amount of 0.1 to 2% by weight based on the aqueous recording liquid. The aqueous recording liquid prepared using the monoazo compound of the present invention is used for writing, stamps, inkjet, etc., and provides reddish writing, printing, and printed matter with excellent fastness. The present invention will be specifically explained below with reference to Examples, but the present invention is not limited to these Examples unless the gist thereof is exceeded. In the examples, carboxyl groups and sulfonic acid groups are expressed in free form. Example 1 Formula Dissolve 43 parts by weight of the compound shown in (hereinafter "parts" indicate parts by weight) in 400 parts of water, and heat at 15 to 45°C, pH 2.0 to
6.0 Condensed with 4.6 parts of aniline in 3 hours (secondary condensation), added 3.6 parts of monoethanolamine, kept the temperature at 65°C, and conducted a condensation reaction at PH9.0 to 10.5 for 3 hours (tertiary condensation) . 25 parts of hydrochloric acid was added to this reaction solution, and the solid content was separated and dried to obtain 45 parts of a monoazo compound represented by the following formula. λmax545nm (measured in pure water, the same applies hereinafter) Example 2 Monoazo compound obtained in Example 1 5 parts Diethylene glycol 10 parts Triethylene glycol 5 parts Propylene glycol 10 parts Neugen P (manufactured by Daiichi Kogyo Seiyaku Co., Ltd., Nonion (Surfactant) 0.2 parts and 69.8 parts of water were mixed and stirred, and the mixture was filtered through industrial paper to obtain an aqueous recording liquid. Next, prints were made using this recording liquid using Sharp's IO-700 (inkjet color printer), and the light resistance of the prints was measured using a carbon fade meter. In addition to exhibiting excellent lightfastness, the print also gave excellent results in terms of water resistance. Examples 4 to 20 The compounds shown in the following table were produced in the same manner as in Example 1. The structural formula and its λmax are shown in the table. Further, an aqueous recording liquid was prepared using these compounds in the same manner as in Example 2, and printed using the color printer described above to obtain a red colored printed matter.
【表】【table】
【表】【table】
【表】【table】
【表】
実施例 21
式
で示される化合物36部を水300部に溶解させ温度
15〜30℃、PH2.0〜6.5で下記式
の化合物９部と２時間反応させ（２次縮合）、更
にモノエタノールアミン3.6部を加え、温度を65
℃に保ち、PH9.0〜10.5で３時間反応させた（３
次縮合）。次いでこの反応液に塩酸25部を加え固
形分を別分離、乾燥し、40部の下記式のモノア
ゾ化合物をえた。
実施例 22〜23
実施例21に準じた方法で次の表の化合物を製造
した。表には構造式とそのλmaxを示した。又こ
れらの化合物を用いて実施例２と同様にして水性
記録液を調製し前記カラープリンターにより印刷
し赤色系の印刷物をえた。[Table] Example 21 formula Dissolve 36 parts of the compound shown in 300 parts of water at a temperature of
The following formula at 15-30℃ and PH2.0-6.5 was reacted with 9 parts of the compound for 2 hours (secondary condensation), then 3.6 parts of monoethanolamine was added, and the temperature was raised to 65°C.
℃ and reacted for 3 hours at pH 9.0 to 10.5 (3
condensation). Next, 25 parts of hydrochloric acid was added to this reaction solution, and the solid content was separated and dried to obtain 40 parts of a monoazo compound of the following formula. Examples 22-23 The compounds shown in the following table were produced in a manner similar to Example 21. The structural formula and its λmax are shown in the table. Further, an aqueous recording liquid was prepared using these compounds in the same manner as in Example 2, and printed using the color printer described above to obtain a red colored printed matter.
【表】
（使用例）
実施例２でえられた水性記録液を市販のインキ
未充填フエルト製サインペンに充填し普通紙上に
筆記した。この記録液による筆跡は鮮明な赤色を
呈し、この耐光、耐水堅牢度がすぐれていた。又
フエルトに前記の水性記録液をしみこませゴム印
を用いて捺印したところ赤色の印字がえられこの
印字の耐光、耐水堅牢度がすぐれていた。[Table] (Usage Example) The aqueous recording liquid obtained in Example 2 was filled into a commercially available unfilled felt felt-tip pen and written on plain paper. The handwriting made with this recording liquid had a clear red color, and its light fastness and water fastness were excellent. Further, when felt was impregnated with the aqueous recording liquid and stamped using a rubber stamp, a red print was obtained, and the print had excellent light fastness and water fastness.
Claims (1)
キシル基、スルホン酸基、スルホンアミド基、メ
チル基又は塩素原子で置換されていてもよいアニ
リノ基；Ｎ−メチルアニリノ基；スルホン酸基又
はメチル基で置換されていてもよいフエノキシ
基；炭素数４以内のアルキル基又はアルカノール
基で置換されていてもよいアミノ基；モルホリノ
基；メトキシ基又はエトキシ基を表わす。又ｎは
１又は２を表わす。〕 で表わされるモノアゾ化合物。 ２ 遊離酸として式（Ｉ） 〔式（Ｉ）においてR1、R2は各々独立にカルボ
キシル基、スルホン酸基、スルホンアミド基、メ
チル基又は塩素原子で置換されていてもよいアニ
リノ基；Ｎ−メチルアニリノ基；スルホン酸基又
はメチル基で置換されていてもよいフエノキシ
基；炭素数４以内のアルキル基又はアルカノール
基で置換されていてもよいアミノ基；モルホリノ
基；メトキシ基又エトキシ基を表わす。又ｎは１
又は２を表わす。〕 で表わされるモノアゾ化合物を含有することを特
徴とする水性記録液。[Claims] 1. Formula (I) as a free acid [In formula (I), R 1 and R 2 are each independently an anilino group which may be substituted with a carboxyl group, a sulfonic acid group, a sulfonamide group, a methyl group or a chlorine atom; an N-methylanilino group; a sulfonic acid group, or It represents a phenoxy group which may be substituted with a methyl group; an amino group which may be substituted with an alkyl group or an alkanol group having up to 4 carbon atoms; a morpholino group; a methoxy group or an ethoxy group. Further, n represents 1 or 2. ] A monoazo compound represented by 2 Formula (I) as free acid [In formula (I), R 1 and R 2 are each independently an anilino group which may be substituted with a carboxyl group, a sulfonic acid group, a sulfonamide group, a methyl group or a chlorine atom; an N-methylanilino group; a sulfonic acid group, or It represents a phenoxy group which may be substituted with a methyl group; an amino group which may be substituted with an alkyl group or an alkanol group having up to 4 carbon atoms; a morpholino group; a methoxy group or an ethoxy group. Also, n is 1
or 2. ] An aqueous recording liquid characterized by containing a monoazo compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59042829A JPS60188468A (en) | 1984-03-08 | 1984-03-08 | Monoazo compound and water-based recording fluid containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59042829A JPS60188468A (en) | 1984-03-08 | 1984-03-08 | Monoazo compound and water-based recording fluid containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60188468A JPS60188468A (en) | 1985-09-25 |
| JPH0153976B2 true JPH0153976B2 (en) | 1989-11-16 |
Family
ID=12646850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59042829A Granted JPS60188468A (en) | 1984-03-08 | 1984-03-08 | Monoazo compound and water-based recording fluid containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60188468A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH066684B2 (en) * | 1984-04-24 | 1994-01-26 | 住友化学工業株式会社 | Ink composition for ink jet printing |
| US4931067A (en) * | 1987-03-27 | 1990-06-05 | Sri International | Method or dyeing using phase change dyestuffs |
| US5466282A (en) * | 1993-05-18 | 1995-11-14 | Canon Kabushiki Kaisha | Azo dye compound, ink containing the same, and recording method and instrument using the ink |
| DE19911195A1 (en) * | 1999-03-13 | 2000-09-14 | Clariant Gmbh | Water-soluble red acid dyes, their production and use |
| US6419353B1 (en) * | 2001-03-02 | 2002-07-16 | Hewlett-Packard Company | Magenta ink formulation |
| GB0223601D0 (en) | 2002-10-11 | 2002-11-20 | Avecia Ltd | Monoazo compounds and inks containing them |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5964677A (en) * | 1982-10-05 | 1984-04-12 | Dainippon Ink & Chem Inc | Magenta ink for ink jet printer |
-
1984
- 1984-03-08 JP JP59042829A patent/JPS60188468A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5964677A (en) * | 1982-10-05 | 1984-04-12 | Dainippon Ink & Chem Inc | Magenta ink for ink jet printer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60188468A (en) | 1985-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |