JPS62289682A - Method for dyeing natural and synthetic material by novel tris-azo dye - Google Patents
Method for dyeing natural and synthetic material by novel tris-azo dyeInfo
- Publication number
- JPS62289682A JPS62289682A JP12946986A JP12946986A JPS62289682A JP S62289682 A JPS62289682 A JP S62289682A JP 12946986 A JP12946986 A JP 12946986A JP 12946986 A JP12946986 A JP 12946986A JP S62289682 A JPS62289682 A JP S62289682A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- synthetic material
- azo dye
- dyeing natural
- dyed
- 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
Links
- 238000004043 dyeing Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 229920002994 synthetic fiber Polymers 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 n-octyl Chemical group 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 1
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 description 1
- OVEMTTZEBOCJDV-UHFFFAOYSA-N 4-hexylaniline Chemical compound CCCCCCC1=CC=C(N)C=C1 OVEMTTZEBOCJDV-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- FDECURPHVMNAKO-UHFFFAOYSA-N 4-nonylaniline Chemical compound CCCCCCCCCC1=CC=C(N)C=C1 FDECURPHVMNAKO-UHFFFAOYSA-N 0.000 description 1
- ORKQJTBYQZITLA-UHFFFAOYSA-N 4-octylaniline Chemical compound CCCCCCCCC1=CC=C(N)C=C1 ORKQJTBYQZITLA-UHFFFAOYSA-N 0.000 description 1
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 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 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 231100000150 mutagenicity / genotoxicity testing Toxicity 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
（イ）産業上の利用分野
本発明は、遊離酸の形で下記一般式（Ｉ）（式中、Ｒは
Ｃ４〜ＣＬ、のアルキル基を示す。）で表わされるトリ
スアゾ染料を使用することを特徴とする天然および合成
材料の染色法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (A) Industrial Application Field The present invention provides a free acid represented by the following general formula (I) (wherein R represents an alkyl group of C4 to CL). It relates to a method for dyeing natural and synthetic materials, characterized in that it uses trisazo dyes.
（ロ）従来の技術及び問題点
従来、天然および合成の材料を黒色に染色するために、
ベンジジン系化合物を母体とする染料が大量に使用され
てきたが、近年これら染料の母体となるベンジジンに発
癌性があることが問題となって、その生産は中止されて
おり、これにとって代わる代替品の開発も種々なされて
いるものの、いずれも未だ十分満足すべき結果は得られ
ていない現状である。(b) Conventional techniques and problems Conventionally, in order to dye natural and synthetic materials black,
Dyes based on benzidine-based compounds have been used in large quantities, but in recent years, the carcinogenicity of benzidine, the base of these dyes, has become a problem, and their production has been discontinued. Although various developments have been made, none of them have yet produced sufficiently satisfactory results.
環境衛生の面から安全性のより高く而も染色効果の高い
黒色染料の要望される所以である。This is why there is a demand for a black dye that is safer and has a higher dyeing effect in terms of environmental hygiene.
本発明者らは、鋭意研究の結果、新規トリスアゾ染料が
水によく溶解し、ビルドアツプ性にすぐれていると共に
、変異原性試験（エームズ法）においても陰性を示すも
のであり、これを用いることにより、染着の良好な、よ
り安全性の高い染色物が得られることを見出し、本発明
を成すに至ったのである。As a result of extensive research, the present inventors found that the new trisazo dye dissolves well in water, has excellent build-up properties, and also showed negative results in a mutagenicity test (Ames method). They discovered that a dyed product with good dyeing and higher safety can be obtained by this method, leading to the completion of the present invention.
（ハ）問題を解決するための手段
本発明は遊離酸の形で下記一般式（Ｉ）で示されるトリ
スアゾ染料を使用することを特徴とする天然および合成
材料の染色法である。(c) Means for Solving the Problems The present invention is a method for dyeing natural and synthetic materials, which is characterized by using a trisazo dye represented by the following general formula (I) in the form of a free acid.
（式中、ＲはＣ４〜Ｃｔｓのアルキル基を示す、）一般
式（Ｉ）で示されるトリスアゾ染料においてＲで示され
るＣ４〜Ｃ１，のアルキル基としては、例えば、ｎ−ブ
チル、ｔ−ブチル、ｎ−ヘキシル、ｎ−オクチル、ｎ−
ノニル、ｎ−ドデシル、１ｓｏ−ドデシル、ステアリル
基等が挙げられる。(In the formula, R represents a C4-Cts alkyl group.) Examples of the C4-C1 alkyl group represented by R in the trisazo dye represented by the general formula (I) include n-butyl, t-butyl , n-hexyl, n-octyl, n-
Examples include nonyl, n-dodecyl, 1so-dodecyl, and stearyl groups.
一般式（Ｉ）で示されるトリスアゾ染料は、例えば以下
に示すような方法で製造することができる。すなわち、
ｐ−ニトロアニリンとＨ酸を通常の方法でカップリング
してモノアゾ色素を得る。The trisazo dye represented by the general formula (I) can be produced, for example, by the method shown below. That is,
The monoazo dye is obtained by coupling p-nitroaniline and H acid in a conventional manner.
ついで通常用いられる還元剤、例えば硫化ソーダでニト
ロ基を還元した後、ジアゾ化し、メタミンスルホン酸に
カップルさせる。さらにＣ１〜Ｃ１゜のアルキル基を有
するアニリンのジアゾニウム塩を添加しカップルさせ目
的物を得ることができる。The nitro group is then reduced with a commonly used reducing agent, such as sodium sulfide, followed by diazotization and coupling to methanesulfonic acid. Furthermore, a diazonium salt of aniline having an alkyl group of C1 to C1° is added and coupled to obtain the desired product.
一般式（Ｉ）で示されるトリスアゾ染料においてＲで示
されるＣ４〜Ｃよ、のアルキル基を有するアニリンの具
体的なものとしては、例えばｐ−ｎ−ブチルアニリン、
ｐ−ｔ−ブチルアニリン、 ｐ−ｎ−へキシルアニリン
、ｐ−ｎ−オクチルアニリン、ｐ−ｎ−ノニルアニリン
、ｐ−ｎ−ドデシルアニリン、ｐ−１ｓｏ−ドデシルア
ニリン、Ｐ−ステアリルアニリン等が挙げられる。Specific examples of the aniline having a C4 to C alkyl group represented by R in the trisazo dye represented by the general formula (I) include p-n-butylaniline,
Examples include p-t-butylaniline, p-n-hexylaniline, p-n-octylaniline, p-n-nonylaniline, p-n-dodecylaniline, p-1so-dodecylaniline, P-stearylaniline, etc. It will be done.
叙上の製法にて得られるところの、本発明に係る遊離酸
の形で一般式（Ｉ）で示されるトリスアゾ染料の具体例
を例示すると、表１の通りである。Table 1 shows specific examples of the trisazo dye represented by the general formula (I) in the form of a free acid according to the present invention, which is obtained by the above production method.
なお、該トリスアゾ染料は、所望のアルカリでアルカリ
塩となすことにより、溶解性の良い、安全性の高い水溶
性染料が得られる。この場合におけるアルカリ源には、
水酸化ナトリウム、水酸化カリウム、水酸化リチウム、
アンモニア水等が用いられる。By converting the trisazo dye into an alkali salt with a desired alkali, a water-soluble dye with good solubility and high safety can be obtained. The alkaline source in this case is
Sodium hydroxide, potassium hydroxide, lithium hydroxide,
Ammonia water etc. are used.
（ニ）ズ施例
実施例１
綿糸を次の条件で染色し青味黒色の染色糸を得た。染色
糸の耐光堅牢度はＪ Ｉ ５−Ｌ−０８４２゜洗ｇｌ
ａ！Ｌｔｆ！、度はＪ Ｉ ５−Ｌ−０８４４（Ａ−２
）によった。(N) Examples Example 1 Cotton yarn was dyed under the following conditions to obtain a bluish-black dyed yarn. The light fastness of the dyed yarn is J I 5-L-0842° wash gl.
a! Ltf! , the degree is J I 5-L-0844 (A-2
) according to
式（２） （７）染料５．０％ ｏ、ｗ、ｆ無水硫酸ナ
トリウム ２０．０％ｏ、ｗ、ｆソーダ灰
２．０％ ｏ、ｗ、ｆ浴比 １：
４０
温度・時間 １００℃、６０分染色物は
射光４級、洗濯３級の堅牢度を有していた。Formula (2) (7) Dye 5.0% o, w, f anhydrous sodium sulfate 20.0% o, w, f soda ash
2.0% o, w, f bath ratio 1:
40 Temperature/time: 100°C, 60 minutes The dyed product had a fastness of 4th grade to sunlight and 3rd grade to washing.
実施例２ 絹紡糸を次の条件で染色し、青味黒色の染色糸を得た。Example 2 The silk spun yarn was dyed under the following conditions to obtain a bluish-black dyed yarn.
式（２）の染料 ５．０％ ｏ、ｗ、ｆ無水
硫酸ナトリウム ２０．０％ｏ、ｗ、ｆ浴比
ｌ：４０
温度・時間 ９５℃、 ６０分染料はよ
いビルドアップ力を有し、染色物は射光６級、洗濯４級
の堅牢度を有していた。Dye of formula (2) 5.0% o, w, f anhydrous sodium sulfate 20.0% o, w, f bath ratio
1:40 Temperature/time: 95°C, 60 minutes The dye had good build-up power, and the dyed product had a fastness of 6th grade to sunlight and 4th grade to washing.
実施例３
スパンナイロン糸を次の条件で染色し、青味黒色の染色
糸を得た。Example 3 Spun nylon yarn was dyed under the following conditions to obtain a bluish-black dyed yarn.
式（２）の染料 ５．０％ ｏ、ｗ、ｆ硫酸
アンモニウム ４．０％ ｏ、ｗ、ｆ浴比
１：４０
温度・時間 １００℃、６０分染料は
よいビルドアップ力を有し、染色物は射光５Ｒ１洗濯５
級の堅牢度を有していた。Dye of formula (2) 5.0% o, w, f ammonium sulfate 4.0% o, w, f bath ratio
1:40 Temperature/time: 100℃, 60 minutes The dye has good build-up power, and the dyed product is washed with 5 R1 of light.
It had a high level of fastness.
実施例４ 絹紡糸を次の条件で染色し、青味黒色の染色糸を得た。Example 4 The silk spun yarn was dyed under the following conditions to obtain a bluish-black dyed yarn.
式（Ｉ）の染料 １０．０％ ｏ、ｗ、ｆ無
水硫酸ナトリウム ２０．０％ ０．ν、ｆ浴比
１：４０
温度・時間 ９５℃、６０分染色物はよ
い堅牢度を有していた。Dye of formula (I) 10.0% o, w, f anhydrous sodium sulfate 20.0% 0. ν, f Bath ratio 1:40 Temperature/time 95°C, 60 minutes The dyed product had good fastness.
実施例５
スパンナイロン糸を次の条件で染色し、青味黒色の染色
糸を得た、。Example 5 Spun nylon yarn was dyed under the following conditions to obtain a bluish-black dyed yarn.
式（３）の染料 １０．０％ ｏ、ｗＪ硫酸
アンモニウム ４．０％ ｏ、ｗＪ浴比
１：５０
温度・時間 １００’Ｃ，６０分染料
は、よいビルドアップ力を有し、染色物はよい堅牢度を
有していた。Dye of formula (3) 10.0% o, wJ Ammonium sulfate 4.0% o, wJ bath ratio
1:50 Temperature/Time 100'C, 60 minutes The dye had good build-up power and the dyeing had good fastness.
Claims (1)
染料を使用することを特徴とする天然および合成材料の
染色法。 ▲数式、化学式、表等があります▼（ I ） （式中、ＲはＣ＿４〜Ｃ＿１＿０のアルキル基を示す。 ）[Claims] A method for dyeing natural and synthetic materials, characterized by using a trisazo dye represented by the following general formula (I) in the form of a free acid. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R represents an alkyl group of C_4 to C_1_0.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12946986A JPS62289682A (en) | 1986-06-03 | 1986-06-03 | Method for dyeing natural and synthetic material by novel tris-azo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12946986A JPS62289682A (en) | 1986-06-03 | 1986-06-03 | Method for dyeing natural and synthetic material by novel tris-azo dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62289682A true JPS62289682A (en) | 1987-12-16 |
Family
ID=15010261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12946986A Pending JPS62289682A (en) | 1986-06-03 | 1986-06-03 | Method for dyeing natural and synthetic material by novel tris-azo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62289682A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5258505A (en) * | 1991-07-26 | 1993-11-02 | Canon Kabushiki Kaisha | Trisazo compounds, and dye compositions containing same |
| US5423906A (en) * | 1992-08-24 | 1995-06-13 | Zeneca Limited | Trisazo dyes, inks comprising same and their use in ink jet printing |
-
1986
- 1986-06-03 JP JP12946986A patent/JPS62289682A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5258505A (en) * | 1991-07-26 | 1993-11-02 | Canon Kabushiki Kaisha | Trisazo compounds, and dye compositions containing same |
| US5423906A (en) * | 1992-08-24 | 1995-06-13 | Zeneca Limited | Trisazo dyes, inks comprising same and their use in ink jet printing |
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