JPS62172062A - Triazine compound - Google Patents
Triazine compoundInfo
- Publication number
- JPS62172062A JPS62172062A JP61013375A JP1337586A JPS62172062A JP S62172062 A JPS62172062 A JP S62172062A JP 61013375 A JP61013375 A JP 61013375A JP 1337586 A JP1337586 A JP 1337586A JP S62172062 A JPS62172062 A JP S62172062A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- dyeing
- formula
- type
- halogen
- 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
- -1 Triazine compound Chemical class 0.000 title claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 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 claims abstract description 6
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims abstract description 4
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims abstract description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000004056 anthraquinones Chemical class 0.000 claims abstract description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 33
- 238000004043 dyeing Methods 0.000 abstract description 28
- 239000000835 fiber Substances 0.000 abstract description 25
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 229920000728 polyester Polymers 0.000 abstract description 13
- 239000000986 disperse dye Substances 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 description 17
- 238000000034 method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000004744 fabric Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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 compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000001000 anthraquinone dye Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 150000003918 triazines Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、たとえばセルロース繊維類用染料として有用
な新規なトリアジン系化合物に関するものである。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel triazine compound useful as a dye for cellulose fibers, for example.
従来の技術
従来、セルロース繊維を染色する場合には、反応性染料
を使用し、炭酸ナトリウム、炭酸カリウム、水酸化ナト
リウム等の酸結合剤および塩化ナトリウム、硫酸ナトリ
ウム等の電解質の存在下に、pH/ 0以上で、温度/
p 0℃以下の条件下で行う方法が採用されている。Conventional technology Traditionally, when dyeing cellulose fibers, reactive dyes are used, and pH is adjusted in the presence of acid binders such as sodium carbonate, potassium carbonate, and sodium hydroxide, and electrolytes such as sodium chloride and sodium sulfate. / Above 0, the temperature /
A method is adopted in which the process is carried out under conditions of p 0°C or lower.
ところが、近年セルロース繊維とその他の繊維、特にポ
リエステル繊維との混紡布等の需要が増大し、この様な
セルロース/ポリエステル混合繊維(以下単に0/P繊
維と記すことがある。)を染色するためには、セルロー
ス繊維に対する染料および染色条件とポリエステル繊維
に対する染料および染色条件とをそれぞれに適用する必
要があった。それはポリエステル繊維を染色するための
染料および染色条件がセルロース繊維に対するそれと、
大きく相違するからであった。すなわちポリエステル繊
維を染色するためには、分散染料を使用し、温度約73
0℃で染色する必要があったためである。However, in recent years, the demand for blended fabrics of cellulose fibers and other fibers, especially polyester fibers, etc. has increased, and in order to dye such cellulose/polyester mixed fibers (hereinafter sometimes simply referred to as 0/P fibers). To do this, it was necessary to apply dyes and dyeing conditions to cellulose fibers and dyes and dyeing conditions to polyester fibers, respectively. That is, the dye and dyeing conditions for dyeing polyester fiber are the same as those for cellulose fiber.
This was because there was a big difference. That is, to dye polyester fibers, disperse dyes are used and the temperature is about 73℃.
This is because it was necessary to dye at 0°C.
たとえば、上記C/P繊維を同一の工程で染色するとす
れば、反応性染料と分散染料との組合せで二つの異なる
染料を使用し染色を行わせることとなり、これにはいく
つかの問題があった。For example, if the C/P fibers mentioned above were to be dyed in the same process, two different dyes would be used in combination, a reactive dye and a disperse dye, which would pose several problems. Ta.
すなわち、反応性染料をセルロース繊維側に充分染着さ
せるためには酸結合剤によりpHを10以上とすること
が必要となり、酸結合剤の存在は分散染料の分解を促進
し分散染料のポリエステル繊維への染着が不充分となる
。一方、分散染料をポリエステル繊維側に染着させるた
めには高温条件(逸常/3o℃)を必要とするが、上記
高声下における高温下では反応性染料の加水分解を促進
し、セルロース繊維への染着が著しく阻害されることと
なる。したがってこの櫟なayp 繊維を染色する場合
には、セルロースまたはポリエステルの一方の繊維を染
色した後、別浴により他の一方の繊維を染色する二浴法
が一般的に行われることとなるのである。In other words, in order to dye the reactive dye sufficiently on the cellulose fiber side, it is necessary to use an acid binder to raise the pH to 10 or more. Dyeing is insufficient. On the other hand, in order to dye disperse dyes on the polyester fiber side, high-temperature conditions (normally 3oC) are required, but at high temperatures under the above-mentioned high-pitched conditions, the hydrolysis of reactive dyes is promoted, and cellulose fibers are The dyeing will be significantly inhibited. Therefore, when dyeing this straight ayp fiber, a two-bath method is generally used in which one fiber, cellulose or polyester, is dyed and then the other fiber is dyed in a separate bath. .
発明が解決しようとする問題点
本発明は、分散染料によりポリエステル繊維合物を提供
しようとするものである。Problems to be Solved by the Invention The present invention seeks to provide a polyester fiber compound using a disperse dye.
問題点を解決するだめの手段
前記の問題点は、特定の構造式を有する本発明のトリア
ジン系化合物により解決することができたのである。Means for Solving the Problems The above problems could be solved by the triazine compound of the present invention having a specific structural formula.
すなわち、本発明のトリアジン系化合物は、一般式(1
)
〔式中、Dはモノアゾ系、ポリアゾ系、金属錯体アゾ系
、アントラキノン系、フタロシアニン系またはホルマザ
ン系の色素残基を表わし、R1は水素原子または置換基
を有していてもよいアルキル基を表わし、Xはハロゲン
原子を表わし、Yは水素原子、ハロゲン原子または置換
基を有していてもよいアルキル基を表わし、2は−ca
=CH=CH2または−または −(!H2CH,08
0,Hを表わす)で示されるトリアジン系化合物である
。That is, the triazine compound of the present invention has the general formula (1
) [In the formula, D represents a monoazo-based, polyazo-based, metal complex azo-based, anthraquinone-based, phthalocyanine-based or formazan-based dye residue, and R1 represents a hydrogen atom or an alkyl group which may have a substituent. where X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and 2 represents -ca
=CH=CH2 or -or -(!H2CH,08
0, H) is a triazine-based compound.
本発明の一般式CI)で表わされるトリアジン系化合物
において、って表わされる色素残基としては例えば次の
ものか挙げられる。In the triazine compound represented by the general formula CI) of the present invention, the dye residue represented by is exemplified by the following.
(1)モノアゾ系色素残基
(2) ポリアゾ系色素残基
(3)金属錯体アゾ系色素残基
(4)アントラキノン系色素残基
(5)7タロシアニン系色素残基
(6)ホルマザン系色素残基
またR1としては水素原子の外にメチル基、エチル基、
プ、チル基、β−ヒドロキシエチル基等の置換基を有し
ていてもよいアルキル基が挙げられ、Xで表わされるハ
ロゲン原子としては塩素原子、フッ素原子、臭素原子が
挙げられる。(1) Monoazo dye residue (2) Polyazo dye residue (3) Metal complex azo dye residue (4) Anthraquinone dye residue (5) 7-thalocyanine dye residue (6) Formazan dye residue In addition to the hydrogen atom, the group R1 includes a methyl group, an ethyl group,
Examples of the alkyl group which may have a substituent such as a methyl group, a β-hydroxyethyl group, and a .beta.-hydroxyethyl group, and examples of the halogen atom represented by X include a chlorine atom, a fluorine atom, and a bromine atom.
Yで表わされるハロゲン原子およびアルキル基としては
、上述と同様のものが挙げられ、夫々塩素原子およびメ
チル基が好適である。The halogen atom and alkyl group represented by Y include those mentioned above, with chlorine atom and methyl group being preferred, respectively.
前足一般式〔I〕で表わされるトリアジン系化合物は次
のようにして製造することができる。The triazine compound represented by the general formula [I] can be produced as follows.
たとえば一般式Cn)
(式中、D 、 R’及び又は前記定義と同義全表わす
)で示される化合物2モル割合と、下記一般02z
(式中、Y及び2は前記定義と同義を表わす)で示され
るジアミン化合物1モル割合とを縮合させることによシ
、前足一般式〔■〕のトリアジ・ン系化合物を製造する
ことができる。For example, a 2 molar proportion of a compound represented by the general formula Cn) (in which D , R' and/or all have the same meanings as the above definitions) and the following general 02z (in the formula, Y and 2 have the same meanings as the above definitions). By condensing with 1 molar proportion of the diamine compound shown, a triazine compound of the general formula [■] can be produced.
なお、上記一般式〔■〕で示されるジアミン化合物は次
のようにして製造することができる。Incidentally, the diamine compound represented by the above general formula [■] can be produced as follows.
たとえば下記一般式〔■〕
(式中、Yは前記定義と同義を表わす)で示される化合
物をクロルスルホン酸中で反応させ、下記一般式〔v〕
(式中、Yは前記定義と同義を表わす)で示される化合
物とした後、亜硫酸で還元してスルフィン酸とし、次い
でこの化合物にエチレンオギサイドを付加させ、一般式
(VD
(式中、Yは前記定義とIiJ義を表わす)で示される
化合物とする。For example, a compound represented by the following general formula [■] (wherein Y represents the same meaning as defined above) is reacted in chlorosulfonic acid, and the compound represented by the following general formula [v] (wherein Y represents the same meaning as defined above) is reacted in chlorosulfonic acid. After forming a compound represented by the general formula (VD (wherein, Y represents the above definition and IiJ definition), it is reduced with sulfite to form a sulfinic acid, and then ethylene oxide is added to this compound. It is a compound that
/′
じさらにエステル化物を希アルカリで処理することによ
り前示一般式〔■〕で示されるジアミン化合物を製造す
ることができる。/' Furthermore, the diamine compound represented by the general formula [■] can be produced by further treating the esterified product with a dilute alkali.
本発明のトリアジン系化合物は、染料、特にセルロース
系繊維用の染料として優れている。The triazine compound of the present invention is excellent as a dye, especially as a dye for cellulose fibers.
すなわち、本発明のトリアジン系化合物で染色しうる繊
維としては木綿、ビスコースレーヨン、キュフラアンモ
ニウムレーヨン、麻などのセルロース系繊維を挙げるこ
とができる。まだ、セルロース系繊維を含有するポリエ
ステル、トリアセテート、ポリアクリロニトリル、ポリ
アミド、羊毛、絹などの混合繊維中の該セルロース系繊
維はもちろん良好に染色することができる。That is, examples of fibers that can be dyed with the triazine compound of the present invention include cellulose fibers such as cotton, viscose rayon, cufurammonium rayon, and hemp. However, cellulose fibers in mixed fibers such as polyester, triacetate, polyacrylonitrile, polyamide, wool, silk, etc. containing cellulose fibers can of course be dyed well.
本発明のジスアゾ系化合物を使用する繊維の染色方法に
おいては、セルロース系以外の繊維を染色するに必要な
染料、例えばCo1our Index(第3版)に記
載されている分散染料などを同時に染浴に加えて染色す
ることができる。In the fiber dyeing method using the disazo compound of the present invention, dyes necessary for dyeing non-cellulose fibers, such as disperse dyes described in Co1our Index (3rd edition), are added to the dye bath at the same time. In addition, it can be dyed.
本発明のジスアゾ系化合物を使用してセルロース系繊維
を染色する場合には、たとえば上記一般式〔■〕で示さ
れるジスアゾ系化合物および染色中に染浴をpHk〜1
0に保持するに必要な緩衝剤(たとえば炭酸、リン酸、
酢酸、クエン酸等の酸とそれらの酸のナトリウム塩また
はカリウム塩の単一または混合物で通常0.5〜!、0
−9/を程度)、そして必要に応じて電解質(塩化ナト
リウムまたは硫酸ナトリウム等を通常/〜i r 09
/を程度)を加えた染浴を調製し、この染浴にセルロー
ス系繊維を投入し、温度700〜750℃で、7O−j
O分間加熱することによって良好な染色を行うことがで
きる。When dyeing cellulose fibers using the disazo compound of the present invention, for example, the disazo compound represented by the above general formula [■] and the dye bath during dyeing may be
Buffers necessary to maintain the temperature at 0 (e.g. carbonic acid, phosphoric acid,
Acids such as acetic acid, citric acid, and sodium salts or potassium salts of these acids, singly or in mixtures, usually 0.5~! ,0
-9/), and if necessary electrolytes (sodium chloride or sodium sulfate, etc.)
Prepare a dye bath to which 700-j.
Good dyeing can be achieved by heating for 0 minutes.
また、セルロース系繊維に他の繊維たとえばポリエステ
ル繊維を加えて製造されている混紡布、混繊編物等を染
色するためには、本発明の上記一般式[1)で示される
ジスアゾ系化合物と、上記0o1our Index所
載の分散染料とを上記染浴に添加することにより、セル
ロース系繊維とポリエステル繊維とを一浴一段法により
同時に染色することができる。In addition, in order to dye blended fabrics, blended knitted fabrics, etc. that are produced by adding other fibers such as polyester fibers to cellulose fibers, a disazo compound represented by the above general formula [1] of the present invention, By adding the disperse dye listed in the 0o1our Index to the dye bath, cellulose fibers and polyester fibers can be dyed simultaneously by a one-bath, one-stage method.
また、上記のような混紡布、混繊編物等を染色する場合
に、従来採用されているようにどちらか一方の繊維を染
色した後に同浴で他方の繊維を染色する一浴二段法を通
用してもよく、さらには、本発明のトリアジン系化合物
による染色法とセルロース系繊維以外の繊維に対する染
色法とを組合せて、別々の浴からセルロース系繊維とそ
の他の繊維とを染色する二浴法を採用することも可能で
ある。In addition, when dyeing blended fabrics, blended knitted fabrics, etc., as described above, the conventional one-bath two-step method of dyeing one fiber and then dyeing the other fiber in the same bath is used. Furthermore, a two-bath method in which cellulose fibers and other fibers are dyed from separate baths by combining the dyeing method using the triazine compound of the present invention and the dyeing method for fibers other than cellulose fibers may be used. It is also possible to adopt the law.
実施例
以下、本発明の方法を実施例によって具体的に説明する
が、本発明は以下の実施例に限定されるものではない。EXAMPLES Hereinafter, the method of the present invention will be specifically explained by examples, but the present invention is not limited to the following examples.
実施例/
3.5−ジニトロベンゼンスルホン酸のカリウム塩30
9をクロルスルホニ/ 酸? !r−中に加え、ざ0℃
で二時間攪拌後冷却し氷水中に排出して31j−ジニト
ロベンゼンスルホニルクロライドとした後、亜硫酸す)
IJウム水溶液中、液性をpH=に〜10に保ちつつ
、50〜60℃で3時間攪拌して、スルフィン酸に還元
した。これに同温度でアルカリを加えpHを7〜gに保
持しつつ、エチレンオキサイドを吹き込み、pH変化力
なくなった後、さらに5時間同温度で攪拌することによ
シ得られた下記構造式
で示される化合物を鉄粉・塩酸系で還元した後濃硫酸中
でエステル化して、下記構造式で示されるジアミン化合
物を製造した。Example/ Potassium salt of 3.5-dinitrobenzenesulfonic acid 30
9 is chlorsulfoni/acid? ! Add to r- and heat to 0°C.
After stirring for 2 hours, the mixture was cooled and discharged into ice water to give 31j-dinitrobenzenesulfonyl chloride, followed by sulfite).
The mixture was stirred at 50 to 60° C. for 3 hours in an aqueous solution of IJum while maintaining the pH at ~10 to reduce it to sulfinic acid. Adding an alkali to this at the same temperature and blowing in ethylene oxide while maintaining the pH at 7 to 7 g. After the pH had lost its ability to change, the mixture was stirred at the same temperature for an additional 5 hours to obtain the following structural formula. The compound was reduced with an iron powder/hydrochloric acid system and then esterified in concentrated sulfuric acid to produce a diamine compound represented by the following structural formula.
次いで、下記構造式
で表わされるモノアゾ色素−モル割合と、前記構造式で
表わされるジアミン化合物1モル割合とを、水媒中、3
0〜aO℃で縮合させた後、塩化ナトリウムで塩析して
、下記構造式で示され、そして、下記の可視光吸収によ
る分析値を有する本発明のトリアジン系化合物を製造し
た。Next, a molar proportion of a monoazo dye represented by the following structural formula and a 1 molar proportion of a diamine compound represented by the above structural formula were mixed in an aqueous medium with 3 molar proportions.
After condensation at 0 to aO<0>C, salting out with sodium chloride was carried out to produce a triazine compound of the present invention represented by the following structural formula and having the following visible light absorption analysis values.
〔λmax : 、)9gnrn (水)〕上記構造式
で示される本発明のトリアジン系化合物0.29.芒硝
/A9、緩衝剤としてNamHPO,/2H,OO,1
1fi+およびKH,、PO4θ、7Elを水−〇〇−
に加えて pH=7に調製した染浴に未シルケット綿メ
リヤス70gを入れ、30分を要して720℃迄昇温し
、同温度でbo分間染色した後水洗、ンービング、水洗
、乾燥を行い黄色の染色物を得た。本染料の染着度は非
常に良好で得られた染色物は極めて濃厚であり耐光堅牢
度、耐塩素堅牢度および耐汗−日光堅牢度はいずれも良
好であった。[λmax: ,)9gnrn (water)] The triazine compound of the present invention represented by the above structural formula 0.29. Glauber's salt/A9, NamHPO,/2H,OO,1 as a buffering agent
1fi+ and KH,, PO4θ, 7El in water −〇〇−
In addition, 70 g of unmercerized cotton knitted fabric was placed in a dye bath adjusted to pH = 7, heated to 720°C over 30 minutes, dyed at the same temperature for 10 minutes, washed with water, annealed, washed with water, and dried. A yellow dyeing was obtained. The degree of dyeing of this dye was very good, and the dyed product obtained was extremely rich, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good.
実施例コ
前記実施1例/において製造したジアミン化合物を水媒
中、pH=g、0〜g、s、sθ〜yt’cで7時間攪
拌して、下記構造式
%式%
で示されるジアミン化合物を製造した。Example The diamine compound produced in Example 1 above was stirred in an aqueous medium at pH=g, 0 to g, s, sθ to yt'c for 7 hours to obtain a diamine represented by the following structural formula % Formula % A compound was prepared.
次いで、下記構造式
で示されるモノアゾ色素コモル割合と、前記構造式で表
わされSジアミン化合物1モル割合とを、水媒中30〜
tio℃で縮合させた後塩化カリウムで塩析して、下記
構造式で示され、そして、下記の可視光吸収による分析
値を有する本発明のトリアジン系化合物を製造した。Next, a comol ratio of a monoazo dye represented by the following structural formula and a 1 molar ratio of an S diamine compound represented by the above structural formula are mixed in an aqueous medium at a concentration of 30 to 30%.
After condensation at tio<0>C, salting out with potassium chloride was carried out to produce a triazine compound of the present invention represented by the following structural formula and having the following visible light absorption analysis values.
〔λmax : 5J+Anrn(水)〕上記構造式で
示される本発明のトリアジン系化合物o、xy、芒硝/
61、緩衝剤としてNa、HPO4/2H,Oθ、5y
およびKW2P0.0.0.2 、rを水コθOmtに
加えて調製した染浴に未シルケット綿メリヤス/θ9を
入れ、30分を要して/JO℃迄昇温し、同温度でJO
分間染色した後、水洗、ンービング、水洗、乾燥を行い
赤色の染色物を得た。本染色浴は染色前、後を通じてp
Hgであった。得られた染色物は極めて濃厚で耐光堅牢
度、耐塩素堅牢度、汗−日光堅牢度はいずれも良好であ
った。[λmax: 5J+Anrn (water)] Triazine compound o, xy, mirabilite/of the present invention represented by the above structural formula
61, Na, HPO4/2H, Oθ, 5y as buffering agent
Unmercerized cotton stockinette/θ9 was added to a dye bath prepared by adding KW2P0.0.0.2 and r to water θOmt, and the temperature was raised to /JO℃ over 30 minutes, and at the same temperature JO
After dyeing for a minute, washing with water, nibbling, washing with water, and drying were performed to obtain a red dyed product. This dyeing bath has a p
It was Hg. The dyed product obtained was extremely dense and had good light fastness, chlorine fastness, and sweat-sunlight fastness.
実施例3
実施例/のジアミン化合物の製造において、3、s −
ジニトロベンゼンスルホンfil f 、3.!; −
’)ニトロ−+−メーy−ルベンゼンスルホン酸ニ代、
tた以外は、実施例/と同様にして下記構造式で示され
るジアミン化合物を製造した。Example 3 In the production of the diamine compound of Example/3, s-
dinitrobenzene sulfone fil f, 3. ! ; −
') nitro-+-merbenzenesulfonic acid,
A diamine compound represented by the following structural formula was produced in the same manner as in Example 1, except for the following.
次いで、下記構造式
で示される色素コモル割合と前記構造式で示されるジア
ミン化合物1モル割合を水媒中30〜lIo℃で縮合さ
せた後スプレー乾燥して、下記構造式で示され、そして
、下記の可視光吸収による分析値を有する本発明のトリ
アジン系化合So、C,H,○EIO,H
〔λmax : /s00nm (水〕〕上記構造式で
示される本発明のトリアジン系化合物0.29、
で示されるアントラキノン染料0.2g1芒硝/コ11
緩衝剤としてNa2HPO,/uH,○o、u tiお
よびKl(tPO40,/ 11を水200ydlに加
えて調製した染浴にポリエステル/木綿−50:50の
混紡布101iを入れ、30分KITE’して/3θ℃
迄昇温し、同温度で60分間染色した後、水洗、ンービ
ング、水洗、乾燥を行い同色性良好な青色の染色物を得
た。本染色浴は染色の前、後においてpHgであった。Next, a comol ratio of a dye represented by the following structural formula and a 1 molar ratio of a diamine compound represented by the above structural formula are condensed in an aqueous medium at 30 to 10 °C, and then spray-dried to obtain a product represented by the following structural formula, and Triazine compound of the present invention having the following analytical value by visible light absorption So, C, H, ○EIO, H [λmax: /s00nm (water)] Triazine compound of the present invention represented by the above structural formula 0.29 , Anthraquinone dye 0.2g 1 Glauber's salt/K11
A polyester/cotton-50:50 blended fabric 101i was added to a dye bath prepared by adding Na2HPO, /uH, ○o, u ti and Kl (tPO40, /11) as a buffer to 200 ydl of water, and the mixture was heated for 30 minutes. te/3θ℃
After dyeing at the same temperature for 60 minutes, washing with water, annealing, washing with water, and drying were performed to obtain a blue dyed product with good same color property. The dyeing bath was at pHg before and after dyeing.
また染着性は非常に良好で得られた染色物は極めて濃厚
でおり耐光堅牢度、耐塩素堅牢度および耐汗−日光堅牢
度はいずれも良好であった。Furthermore, the dyeing property was very good, and the dyed product obtained was extremely rich, and the light fastness, chlorine fastness, and sweat-sunlight fastness were all good.
実施例弘
実施例/に準じた方法で下記第1表に示さHる本発明の
トリアジン系化合物を製造し、該化合物により綿布を染
色し、結果を第1表に示したOThe triazine compounds of the present invention shown in Table 1 below were produced by a method similar to Example 1, and cotton cloth was dyed with the compounds, and the results were shown in Table 1.
Claims (1)
、アントラキノン系、フタロシアニン系またはホルマザ
ン系の色素残基を表わし、R^1は水素原子または置換
基を有していてもよいアルキル基を表わし、Xはハロゲ
ン原子を表わし、Yは水素原子、ハロゲン原子または置
換基を有していてもよいアルキル基を表わし、Zは−C
H=CH_2または−CH_2CH_2OSO_3Hを
表わす) で示されるトリアジン系化合物。(1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼……[I] (In the formula, D is a monoazo-based, polyazo-based, metal complex azo-based, anthraquinone-based, phthalocyanine-based, or formazan-based dye) Represents a residue, R^1 represents a hydrogen atom or an alkyl group that may have a substituent, X represents a halogen atom, and Y represents a hydrogen atom, a halogen atom, or an optional substituent. represents an alkyl group, Z is -C
A triazine compound represented by H=CH_2 or -CH_2CH_2OSO_3H.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61013375A JPH0662873B2 (en) | 1986-01-24 | 1986-01-24 | Triazine compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61013375A JPH0662873B2 (en) | 1986-01-24 | 1986-01-24 | Triazine compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62172062A true JPS62172062A (en) | 1987-07-29 |
JPH0662873B2 JPH0662873B2 (en) | 1994-08-17 |
Family
ID=11831349
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61013375A Expired - Lifetime JPH0662873B2 (en) | 1986-01-24 | 1986-01-24 | Triazine compounds |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0662873B2 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0251565A (en) * | 1988-06-21 | 1990-02-21 | Ciba Geigy Ag | Azo dye |
WO2000008104A1 (en) * | 1998-07-31 | 2000-02-17 | Basf Aktiengesellschaft | Reactive dyes containing a linkage |
CN112745247A (en) * | 2020-12-31 | 2021-05-04 | 湖北丽源科技股份有限公司 | Novel dye intermediate, novel dye and preparation method thereof |
CN112778172A (en) * | 2020-12-31 | 2021-05-11 | 湖北丽源科技股份有限公司 | Novel brilliant blue dye intermediate, reactive brilliant blue dye and preparation method and application thereof |
CN114752229A (en) * | 2022-04-11 | 2022-07-15 | 黄山普米特新材料有限公司 | Reactive grey dye |
-
1986
- 1986-01-24 JP JP61013375A patent/JPH0662873B2/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0251565A (en) * | 1988-06-21 | 1990-02-21 | Ciba Geigy Ag | Azo dye |
WO2000008104A1 (en) * | 1998-07-31 | 2000-02-17 | Basf Aktiengesellschaft | Reactive dyes containing a linkage |
JP2002522587A (en) * | 1998-07-31 | 2002-07-23 | ビーエーエスエフ アクチェンゲゼルシャフト | Reactive dye having a chain |
CN112745247A (en) * | 2020-12-31 | 2021-05-04 | 湖北丽源科技股份有限公司 | Novel dye intermediate, novel dye and preparation method thereof |
CN112778172A (en) * | 2020-12-31 | 2021-05-11 | 湖北丽源科技股份有限公司 | Novel brilliant blue dye intermediate, reactive brilliant blue dye and preparation method and application thereof |
CN114752229A (en) * | 2022-04-11 | 2022-07-15 | 黄山普米特新材料有限公司 | Reactive grey dye |
Also Published As
Publication number | Publication date |
---|---|
JPH0662873B2 (en) | 1994-08-17 |
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