JPS63256660A - Water-soluble disazo dye - Google Patents
Water-soluble disazo dyeInfo
- Publication number
- JPS63256660A JPS63256660A JP9159787A JP9159787A JPS63256660A JP S63256660 A JPS63256660 A JP S63256660A JP 9159787 A JP9159787 A JP 9159787A JP 9159787 A JP9159787 A JP 9159787A JP S63256660 A JPS63256660 A JP S63256660A
- Authority
- JP
- Japan
- Prior art keywords
- dyes
- formula
- water
- dye
- disazo dye
- 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.)
- Granted
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052731 fluorine Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 28
- 238000004043 dyeing Methods 0.000 abstract description 10
- 239000000835 fiber Substances 0.000 abstract description 7
- 239000004744 fabric Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000004040 coloring Methods 0.000 abstract 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 239000000979 synthetic dye Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 210000004243 sweat Anatomy 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は新規な構造を有する紺色の水溶性ジスアゾ色素
に関するものであシ、詳しくは、構造中にハロゲノメト
キシトリアジン型反応基およびビニルスルホン型反応基
を有し、％にセルロースの染色に用いた場合、針元、塩
素、汗１日光堅牢度およびビルドアツプ性の良好な被染
物を得ることのできる水溶性ジスアゾ色素に関するもの
である。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a dark blue water-soluble disazo dye having a novel structure. The present invention relates to a water-soluble disazo dye which has a reactive group and, when used for dyeing cellulose, can provide dyed articles with good needle base, chlorine, sweat, sunlight fastness and build-up properties.
（従来の技術）
セルロースまたは含窒素繊維を含有する稙維類を染色す
る場合、通常、水溶性の反応性染料が用いられるが、こ
の反応性染料としては、均染性に優れ、且つ、被染物を
濃厚に染色することができ、しかも、染色物の各種堅牢
度も良好なものが要求される。このような反応性染料の
特性は染料の基本骨格、置換基、反応基及びこれらの組
合せにより微妙に異なシ、従来、種々の構造の染料が提
案されている。(Prior art) When dyeing cellulose or filaments containing nitrogen-containing fibers, water-soluble reactive dyes are usually used. It is required that the dyed material can be dyed deeply and that the dyed material has good fastness properties. The properties of such reactive dyes vary slightly depending on the basic skeleton of the dye, substituents, reactive groups, and combinations thereof, and dyes with various structures have been proposed in the past.
例えば特開昭６／−／／１４す７号は、 Ｓ ＯｓＯミ
椹または−８０，ＯＬＯ＆Ｘの少くとも７つとを提案し
ている。しかし、上記公開特許明細書に具体的に示され
ている染料は必ずしも射光、塩素、汗１日光盟牢度及び
ビルドアツプ性の良好な被染物を与えるものではない。For example, Japanese Patent Application Laid-Open No. 1983-14-14 proposes at least seven of SOSOMIZAWA or -80, OLO&X. However, the dyes specifically shown in the above-mentioned patent specifications do not necessarily provide dyed articles with good resistance to sunlight, chlorine, perspiration, and build-up properties.
例えば、丁記榊造式〔ア〕〜〔イ〕の染料が具体的に示
されているが、
しよ
〔ア〕で示される染料は塩素、汗７日光堅牢度が致命的
に劣シ、また〔イ〕で示される染料はビルドアツプ性が
劣る。For example, the dyes of Choki Sakakizou style [A] to [B] are specifically shown, but the dye shown by Shiyo [A] has fatally poor fastness to chlorine, sweat 7, and sunlight. Furthermore, the dye shown in [A] has poor build-up properties.
（発明が解決しようとする問題点〕
本発明は例えば浸染々色においては射光、塩素、汗１日
光堅牢度がいずれも優れ、かつビルドアツプ性の良好な
被染物を与えることのできる新しいジスアゾ色素を提供
することを目的とするものである。(Problems to be Solved by the Invention) The present invention provides a new disazo dye that has excellent fastness to light, chlorine, and perspiration in dyed dyes, and can provide dyed articles with good build-up properties. The purpose is to provide
（問題点′ｊｆＩ：解決するための手段）本発明の色素
は、遊離酸の形で下記一般式印Ｗは−Ｑｌ＝Ｑ）ｌ、基
または−ｏａｔａａｔｏｓｏｓｉ基であるンを以下、本
発明の詳細な説明すると、本発明の水溶性ジスアゾ色素
釦おいてＤが
げられる。(Problem 'jfI: Means for Solving) The dye of the present invention, in the form of a free acid, has the following general formula W is -Ql=Q)l, a group or -oataatososi group. To explain in detail, D is included in the water-soluble disazo dye button of the present invention.
本発明のジスアゾ色素は、遊離酸の形、またはその塩の
形で存在するが、塩としては、通常アルカリ金属塩およ
びアルカリ土類金属塩があげられ％％にリチウム塩、ナ
トリウム塩、カリウム塩が好ましい。The disazo dye of the present invention exists in the form of a free acid or a salt thereof, and salts usually include alkali metal salts and alkaline earth metal salts, and %% include lithium salts, sodium salts, and potassium salts. is preferred.
前示一般式〔ｌ〕で示される本発明のジスアゾ色素は、
以下の方法によシ製造することができる。The disazo dye of the present invention represented by the general formula [l] is:
It can be manufactured by the following method.
例えば、下記一般式〔］〕
Ｄ −ＨＨ，−・・拳・・・・・・・ ［１１）（式
中、Ｄ鉱前示定義に同じ）
で示される化合物を常法釦従りてジアゾ化した後、下記
一般式［１３
（式中、Ｘは前記定義に同じ）
で示される七ノアゾ化合物と水性媒体中、０〜５℃の温
度でｐＨ７〜ｔＶＣてカップリングさせることによシ製
造することができる。For example, a compound represented by the following general formula []] D -HH, -... Fist... [11) (in the formula, the same as the above definition of D mineral) is prepared using a conventional method or diazo After that, the product is produced by coupling with a heptanoazo compound represented by the following general formula [13 (wherein, X is the same as defined above)] in an aqueous medium at a temperature of 0 to 5°C and pH 7 to tVC. can do.
（作 用ン
本発明のジスアゾ色素を染料として用いる場合には、対
象となる繊維としては、木綿、ビスコースレーヨン、キ
エプラアンモニウムレーヨン、麻などのセルロース系繊
維、更にポリアミド、羊毛、絹等の含窒素繊維が挙げら
れるが、セルロース繊維が特に望ましい。また、これら
の繊維は、例えば、ポリエステル、トリアセテート、ポ
リアクリロニトリルなどとの混合繊維として用いても差
し支えない。(Function) When the disazo dye of the present invention is used as a dye, target fibers include cellulose fibers such as cotton, viscose rayon, Kiepra ammonium rayon, and hemp, as well as polyamide, wool, silk, etc. Nitrogen-containing fibers are mentioned, and cellulose fibers are particularly preferred.These fibers may also be used as mixed fibers with, for example, polyester, triacetate, polyacrylonitrile, and the like.
本発明のジスアゾ色素を用いてセルロースまたは含窒素
繊維類を染色するＩｃは１通常、重炭酸ソーダ、炭酸ソ
ーダ等め無機アルカリ、またはトリエチルアミン等の有
機塩基よシなる酸結合剤を用い、これら酸結合剤の存在
下、常法に従って染色することができる。Ic for dyeing cellulose or nitrogen-containing fibers using the disazo dye of the present invention is usually carried out using an acid binder such as an inorganic alkali such as sodium bicarbonate or soda carbonate, or an organic base such as triethylamine. It can be dyed according to a conventional method in the presence of.
本発明の染色法としては、特に浸染法が好適であシ、染
色温度は通常、参〇〜６０℃程度が好適である。As the dyeing method of the present invention, dip dyeing is particularly suitable, and the dyeing temperature is usually about 0 to 60°C.
さらに、本発明のジスアゾ色素はコールドパッドパッチ
法、パッドスチーム法、捺染法などの染色法に適用する
こともできる。Furthermore, the disazo dye of the present invention can also be applied to dyeing methods such as cold pad patch method, pad steam method, and textile printing method.
実施例
次に、本発明を実施例によシ更に具体的に説明するが、
本発明はその要旨を超えない限シ以下の実施例に限定さ
れるものではない。EXAMPLES Next, the present invention will be explained in more detail with reference to examples.
The present invention is not limited to the following examples as long as they do not exceed the gist thereof.
実施例１
で示されるアミノナフタレン化合物１モル割合で示され
る化合物１モル割合と水性媒体中、０〜５℃、ｐＨ７〜
ｔで３時間カップリングさせた後、塩化ナトリウムで塩
析して下記の構造式（遊離酸の形で示す〕および可視光
吸収による分析値を有するジスアゾ色素を得た。In an aqueous medium with 1 molar proportion of the aminonaphthalene compound shown in Example 1, 0 to 5°C, pH 7 to
After coupling at t for 3 hours, salting out with sodium chloride yielded a disazo dye having the following structural formula (shown in free acid form) and analytical values by visible light absorption.
Ａ ／ Ｊ ｎｍ
上記のようにして得られたジスアゾ色素０．コｔ％ｏ、
ａｔ、ｏ、ｔｒｔを夫々水２００１１Ｌｌに溶解し、芒
硝ｉｏｙを加え、溶解してｖ！４整した染浴に未シルケ
ット綿メリヤスｉｏｔを浸漬し、３ｏ分ｔ−要して６０
℃まで昇温した。次いで、炭酸ンーダＪ、Ｏｆを添加し
、ｂｏ℃で／時間染色した後、水洗、ソーピング、水洗
、乾燥を行ない緑味紺色の染色物を得た＠
本染料により得られた染色物は均一に染色されておシ、
かつ、極めて濃厚でめシ、ビルドアツブ性にも優れてい
た。すなわち、色素０．コ？を用いて染色した染色布の
耐光堅牢度（Ｊ工５Ｌ−０１４−）は５級、耐塩素竪牢
度（Ｊ工８Ｌ−ｏｇｔａｌに準拠し有効塩素／ Ｏｐｐ
ｍ ）は弘−５級、汗日光堅牢度（ＩＸＢＬ−０１８１
Ａ法アルカリ〕は３級と非常に良好であった。A/J nm Disazo dye obtained as above 0. Kot%o,
Dissolve at, o, and trt in 20011L of water, add mirabilite ioy, dissolve, and v! 4. Soak the unmercerized cotton stockinette in the prepared dye bath for 3 minutes - 60 minutes in total.
The temperature was raised to ℃. Next, after adding carbonate J, Of and dyeing at bo℃/hour, washing with water, soaping, washing, and drying were performed to obtain a greenish dark blue dyed product.@The dyed product obtained with this dye was uniformly It's dyed,
In addition, it was extremely rich and had excellent build-up properties. That is, dye 0. Ko? The light fastness of the dyed fabric (J-ko 5L-014-) is grade 5, and the chlorine resistance (available chlorine/opp according to J-ko 8L-ogtal) is 5th grade.
m) is Hiro-5 grade, sweat and sunlight fastness (IXBL-0181
Method A alkali] was grade 3, which was very good.
実施例コ
第１表に示す本発明のジスアゾ色素（遊離酸の形で示す
）を実施例／の方法Ｋｍじて合成し、実施例／と同様の
方法で綿布を染色したところいずれもピルドアラグは良
好で、射光堅牢度！級、塩素盟牢度ａ−Ｓ級、汗日光堅
牢度は３級と非常に良好であった。EXAMPLE The disazo dyes of the present invention (shown in the form of free acid) shown in Table 1 were synthesized according to the method in Example/Km, and cotton fabric was dyed in the same manner as in Example/. Good and light fastness! The chlorine resistance was a-S class, and the sweat and sunlight fastness was class 3, which was very good.
第１表Table 1
Claims (1)
は▲数式、化学式、表等があります▼基（ここで、Ｗは
、 −ＣＨ＝ＣＨ＿２基または−ＣＨ＿２ＣＨ＿２ＯＳＯ＿
３Ｈ基である）を表わし、Ｘは塩素原子または弗素原子
を表わす〕で示される水溶性ジスアゾ色素。(1) In the form of a free acid, the following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] [In the formula, D is ▲There are ▲mathematical formulas, chemical formulas, tables, etc.▼group or ▲Mathematical formula , chemical formulas, tables, etc. ▼ group (where W is -CH=CH_2 group or -CH_2CH_2OSO_
3H group), and X represents a chlorine atom or a fluorine atom.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62091597A JPH0762115B2 (en) | 1987-04-14 | 1987-04-14 | Water-soluble disazo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62091597A JPH0762115B2 (en) | 1987-04-14 | 1987-04-14 | Water-soluble disazo dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63256660A true JPS63256660A (en) | 1988-10-24 |
| JPH0762115B2 JPH0762115B2 (en) | 1995-07-05 |
Family
ID=14030964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62091597A Expired - Lifetime JPH0762115B2 (en) | 1987-04-14 | 1987-04-14 | Water-soluble disazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0762115B2 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5757754A (en) * | 1980-09-25 | 1982-04-07 | Nippon Kayaku Co Ltd | Reactive disazo dye |
| JPS61118459A (en) * | 1984-08-30 | 1986-06-05 | チバ−ガイギ アクチエンゲゼルシヤフト | Dyeing or printing of fibrous material by reactive dye |
-
1987
- 1987-04-14 JP JP62091597A patent/JPH0762115B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5757754A (en) * | 1980-09-25 | 1982-04-07 | Nippon Kayaku Co Ltd | Reactive disazo dye |
| JPS61118459A (en) * | 1984-08-30 | 1986-06-05 | チバ−ガイギ アクチエンゲゼルシヤフト | Dyeing or printing of fibrous material by reactive dye |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0762115B2 (en) | 1995-07-05 |
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