JPS63251474A - Water-soluble anthraquinone dye - Google Patents
Water-soluble anthraquinone dyeInfo
- Publication number
- JPS63251474A JPS63251474A JP62085221A JP8522187A JPS63251474A JP S63251474 A JPS63251474 A JP S63251474A JP 62085221 A JP62085221 A JP 62085221A JP 8522187 A JP8522187 A JP 8522187A JP S63251474 A JPS63251474 A JP S63251474A
- Authority
- JP
- Japan
- Prior art keywords
- group
- dye
- water
- formula
- dyeing
- 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
- 239000001000 anthraquinone dye Substances 0.000 title claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 18
- 239000000835 fiber Substances 0.000 abstract description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 6
- 229920003043 Cellulose fiber Polymers 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 cyanomethyl group Chemical group 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- 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
- 239000003513 alkali Substances 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 244000132059 Carica parviflora Species 0.000 description 1
- 235000014653 Carica parviflora Nutrition 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 239000004952 Polyamide Substances 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
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000000137 annealing Methods 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011487 hemp Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000049 pigment Substances 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 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 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- VZPXDCIISFTYOM-UHFFFAOYSA-K trisodium;1-amino-4-[4-[[4-chloro-6-(3-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-3-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC(C=C1S([O-])(=O)=O)=CC=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S([O-])(=O)=O)=C1 VZPXDCIISFTYOM-UHFFFAOYSA-K 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/06—Anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
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青色系の水溶性アントラキ
ノン色素に関するものであシ、詳しくは、構造中にアル
；キシトリアジン型反応基を有し、特に、セルロースま
たは含窒素繊維の染色に用いた場合、各種堅牢度が優れ
ている上、低温域の染色においても良好力染色ができ濃
厚な被染物を刊ることができ、しかも、熱変色性の小さ
い水溶性アントラキノン色素に関するものである。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a blue water-soluble anthraquinone dye having a novel structure. In particular, when used in the dyeing of cellulose or nitrogen-containing fibers, it not only has excellent fastness properties, but also allows for good strength dyeing even in low-temperature dyeing, making it possible to print densely dyed materials. This invention relates to a water-soluble anthraquinone dye with low discoloration.
（従来の技術）
セルロースまたは含窒素繊維を含有する繊維類を染色す
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
合せによシ微妙に異なシ、従来、珊々の構造の染料が提
案されている。(Prior Art) When dyeing fibers containing cellulose or nitrogen-containing fibers, water-soluble reactive dyes are usually used. It is required that the dyed product can be dyed deeply and that the dyed product 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. So far, dyes with a coral structure have been proposed.
例えば、下記構造式〔ア〕で示されるアントラキノン系
染料が知られている。For example, anthraquinone dyes represented by the following structural formula [A] are known.
（ａ、工、Ｒｅａｃｔｉｖｅ Ｂｌｕｅ ２ ）（発明
が解決しようとする問題点）
近年、濃厚染色性及び各種堅牢度が優れている上、省エ
ネルギーの立場から特に、浸染染色法において、例えば
、グ０〜６０℃の低温域でも良好に染色することのでき
る反応性染料が要望されている。しかしながら、一般的
に、モノクロロトリアジン型の反応性染料は７０〜？θ
℃の染色温度で最も優れた染色性を発揮し、グｏ−ｇθ
℃程度の染色温度では濃厚な被染物を得ることは難しい
。例えば、前示構造式〔ア〕で示される染料の場合も、
浸染での適性Ｉ染色温度は？θ℃と高いという問題点を
有している。(A, Engineering, Reactive Blue 2) (Problems to be solved by the invention) In recent years, in addition to being excellent in deep dyeing properties and various fastnesses, from the standpoint of energy saving, especially in the dip dyeing method, for example, There is a need for reactive dyes that can dye well even at low temperatures of 60°C. However, in general, reactive dyes of the monochlorotriazine type are 70~? θ
Demonstrates the best dyeing properties at a dyeing temperature of ℃,
It is difficult to obtain a densely dyed object at a dyeing temperature of about ℃. For example, in the case of the dye represented by the above structural formula [A],
What is the appropriate dyeing temperature for dip dyeing? The problem is that the temperature is as high as θ°C.
本発明者等は、種々検討した結果、特定の構造を持つ新
規なアントラキノン染料を用いることによシ、本発明の
上記の目的が達成されることを見い出し、本発明を完成
するに至った。As a result of various studies, the present inventors have found that the above-mentioned objects of the present invention can be achieved by using a novel anthraquinone dye having a specific structure, and have completed the present invention.
（問題点を解決するための手段）
本発明の要旨は遊離酸の形で、下記一般式〔Ｉ〕〔式中
Ｒ１は低級アルキレン基を表わし、Ｘはハロゲン原子
を表わし、Ｙは一０Ｒ２基（但し、ここでＲ２は水酸基
、カルボキシル基、スルホン酸基、シアノ基もしくはハ
ロゲン原子で置換されていてもよい低級アルキル基であ
る）または−０−ｆＲ３０孟Ｒ４基（但し、ここでＲ３
は低級アルキレン基 Ｒ４は水酸基で置換されていても
よい低級アルキル基、ｎは／〜１０の整数である）を表
わす〕
で示される水溶性アントラキノン色素に存する。(Means for Solving the Problems) The gist of the present invention is a free acid having the following general formula [I] [wherein R1 represents a lower alkylene group, X represents a halogen atom, and Y represents a 10R2 group] (However, R2 here is a hydroxyl group, a carboxyl group, a sulfonic acid group, a cyano group, or a lower alkyl group which may be substituted with a halogen atom) or -0-fR30 MengR4 group (However, R3
represents a lower alkylene group, R4 is a lower alkyl group which may be substituted with a hydroxyl group, and n is an integer from / to 10).
以下、本発明の詳細な説明すると、本発明の水溶性アン
トラキノン色素において、前示一般式ＣＩ）における、
Ｘで表わされるハロゲン原子としては、通常、フッ素原
子、塩素原子、臭素原子が挙げられ、特に、フッ素原子
、塩素原子が好ましい。Hereinafter, the present invention will be described in detail. In the water-soluble anthraquinone dye of the present invention, in the general formula CI),
The halogen atom represented by X usually includes a fluorine atom, a chlorine atom, and a bromine atom, with a fluorine atom and a chlorine atom being particularly preferred.
Ｙで表わされる一ＯＲ２基及び−ｏ＋Ｒ８−ｏヤＲ４基
における Ｒ２およびＲ４で表わされ低級アルキル基と
しては、例えば、メチル基、エチル基、プロピル基等の
炭素数／〜グの直鎖ま念は分岐状のアルキル基が挙げら
れる。尚 Ｒ２で表わされる低級アルキル基は、水酸基
、カルボキシル基、スルホン酸基、シアノ基もしくはハ
ロゲン原子で置換されたものでもよいが、これらの具体
例としては、例えば、コーヒドロキシエテル基、グーヒ
ドロキシブチル基、−一力ルボキシエチル基、コーシア
ノエチル基、シアノメチル基、３−クロロプロピル基な
どが挙げられる。The lower alkyl group represented by R2 and R4 in the 1OR2 group and the -o+R8-oyaR4 group represented by Y is, for example, a methyl group, an ethyl group, a propyl group, etc. An example of this is a branched alkyl group. Note that the lower alkyl group represented by R2 may be substituted with a hydroxyl group, a carboxyl group, a sulfonic acid group, a cyano group, or a halogen atom, and specific examples thereof include, for example, co-hydroxyether group, g-hydroxybutyl group, etc. group, -monocarboxyethyl group, cocyanoethyl group, cyanomethyl group, 3-chloropropyl group, and the like.
又 Ｒ４で表わされる低級アルキル基は、水酸基で置換
されていてもよい。Further, the lower alkyl group represented by R4 may be substituted with a hydroxyl group.
また Ｒ１またはＲ３で表わされる低級アルキレン基と
しては、例えば、メチレン基、エチレン基、プロピレン
基、ブチレン基の辰紫数／〜グのアルキレン基が誉げら
れる。Examples of the lower alkylene group represented by R1 or R3 include alkylene groups having a violet number/~g such as a methylene group, an ethylene group, a propylene group, and a butylene group.
なお、ｎは７〜ＩＯの整数であるが、望ましくは７〜ｇ
の整数である。Note that n is an integer from 7 to IO, preferably from 7 to g
is an integer.
本発明のアントラキノン色素は、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、特にリチウ
ム塩、ナトリウム塩、カリウム塩が好ましい。The anthraquinone 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, particularly lithium salts, sodium salts, and potassium salts. is preferred.
前示一般式ＣＩ）で示される本発明のアントラキノン色
素は、以下の方法によシ製造することができる。The anthraquinone dye of the present invention represented by the general formula CI) can be produced by the following method.
例えば、下記一般式〔■〕
（式中、Ｒ１は前記定義に同じ）
で示される化合物と下記一般式［１１１）（式中、Ｘお
よびＹは前記定義に同じ）で示される化合物１モル割合
を水性媒体中、／θ℃〜４ｔｏ℃の温度で縮合させるこ
とによ多製造することができる。For example, 1 molar ratio of a compound represented by the following general formula [■] (wherein R1 is the same as defined above) and a compound represented by the following general formula [111) (wherein X and Y are the same as defined above) It can be produced by condensing in an aqueous medium at a temperature of /θ°C to 4to°C.
本発明のアントラキノン色素は繊維、布を染色するため
の染料、紙、合成樹脂を着色するための色素、更に、イ
ンクジェット式プリンター用などの色素として広く利用
することができるが、特に染料としての適性が優れてｂ
る。The anthraquinone dye of the present invention can be widely used as a dye for dyeing fibers and cloth, a dye for coloring paper and synthetic resins, and a dye for inkjet printers, but it is particularly suitable as a dye. is excellentb
Ru.
本発明のアントラキノン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、キュ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の混合繊維として用いても
差し支え万い。When the anthraquinone pigment of the present invention is used as a dye, target fibers include cellulose fibers such as cotton, viscose rayon, cuproammonium rayon, and hemp, as well as nitrogen-containing fibers such as polyamide, wool, and silk. cellulose fibers are particularly preferred. Also,
These fibers may be used as mixed fibers of polyester, triacetate, polyacrylonitrile, and the like.
本発明のアントラキノン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には、通常、重炭酸ソーダ、炭
酸ソーダ等の無機アルカリ、ま六はトリエチルアミン等
の有機塩基よりなる酸結合剤を用い、これら酸結合剤の
存在下、相法に従って染色することができる。In order to dye cellulose or nitrogen-containing fibers using the anthraquinone dye of the present invention, an acid binder consisting of an inorganic alkali such as bicarbonate of soda or sodium carbonate, or an organic base such as triethylamine is usually used to bind these acids. It can be dyed according to the phase method in the presence of agents.
本発明の染色法としては、特に浸染法が好適であシ、染
色温度は連相、グθ〜６０℃程度が好適である。本発明
の色素においては、このような低温域の染色温度を採用
しても、濃厚な染色ができる。As the dyeing method of the present invention, dip dyeing is particularly suitable, and the dyeing temperature is preferably continuous phase and about 60°C. With the dye of the present invention, even if a dyeing temperature in such a low temperature range is employed, deep dyeing can be achieved.
さらに、本発明のアントラキノン色素は、コ一ルドパッ
ドバッチ法、パッドスチーム法、捺染法々どの染色法に
適用することもできる。Furthermore, the anthraquinone dye of the present invention can be applied to any dyeing method, such as a cold pad batch method, a pad steam method, or a 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。(Example) 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／
遊離酸の形で下記構造式
で表わされるアントラキノン化合物１モル割合と下記の
構造式
で表わされる化合物１モル割合とを水性媒体中、３０℃
、Ｉ）Ｈ７〜７．！で縮合させた後、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アントラキノン色素を製造
した。Example: 1 molar proportion of an anthraquinone compound represented by the following structural formula in the form of a free acid and 1 molar proportion of a compound represented by the following structural formula in an aqueous medium at 30°C
, I) H7-7. ! After condensation with sodium chloride, salting out with sodium chloride was carried out to produce an anthraquinone dye having the following structural formula (shown in free acid form) and analytical value by visible light absorption.
上記のようにして荀られたアントラキノン色素０．２１
を水２００ ｍｌに溶解し、芒硝／θ２を加え、溶解し
て調整した染浴に未シルケット綿メリヤスｉｏｔを浸漬
し、３０分を要して３０℃まで外淵した。次いで、炭酸
ソーダ３．θｔを添加し、１０℃で／時間染色した後、
水洗、ノーピンク、水洗、乾燥を行ない青色の染色物を
祠た。Anthraquinone dye obtained as above 0.21
was dissolved in 200 ml of water, and Glauber's Salt/θ2 was added. Unmercerized cotton stockinette was immersed in the prepared dye bath and heated to 30° C. for 30 minutes. Next, carbonated soda 3. After adding θt and staining at 10 °C/h,
After washing with water, no pink, washing with water, and drying, the dyed blue color was created.
本染料によシ葡られた染色物は均一に染色されてお９、
かつ、極めて濃厚であシ、耐光堅牢度（Ｊ工Ｓ Ｌ−
１？４ｔ、２）は！級、汗日光堅牢度（Ｊ工Ｓ Ｌ−０
？ｔ！＃Ａ法ア／Ｌ、 カリ）は４を級と非常に良好で
あっ念。The dyed products made with this dye are uniformly dyed9.
In addition, it is extremely thick and light fastness (J Engineering S L-
1?4t, 2) is! grade, sweat and sunlight fastness (J Engineering S L-0
? T! #A Method A/L, Cali) is very good with a grade of 4.
なお、上記染色法において、染色温度をと０℃から２０
℃に変更して同様力染色を行ない、この場合の染色性を
比較したところ、染色温度ｔθ℃の場合と同レベルであ
り念。In addition, in the above dyeing method, the dyeing temperature is 0°C to 20°C.
When the temperature was changed to tθ°C and the same force staining was performed, the staining properties in this case were compared and were found to be at the same level as when the staining temperature was tθ°C.
実施例λ
遊離酸の形で、下記構造式
％式％（）
で示されるアントラキノン色ＸＯ，−２ｆ′ｆ、水コθ
θゴに溶解させ、芒硝！２を加え、溶解して調整した染
浴に未シルケット綿メリヤス／θｔを浸漬し、３０分を
袈してりθ℃迄昇温した。次いで、炭酸ソーダ３．０２
を添加し、グθ℃で／時間染色し九後、水洗、ンービン
グ、水洗、乾燥を行ない青色の染色物を裂た。Example λ In the form of free acid, anthraquinone color XO, -2f′f, water θ, represented by the following structural formula %
Dissolve in θ Go and use mirabilite! The unmercerized cotton knitted fabric/θt was immersed in the prepared dye bath, and the temperature was raised to θ°C for 30 minutes. Next, soda carbonate 3.02
was added and dyed for 9 hours at θ°C, followed by washing with water, annealing, washing with water, and drying to tear the blue dyed product.
本染料により得られた染色物は均一に染色されておフ、
かつ、極めて濃厚であり、耐光堅牢度（Ｊ工ＳＬ−〇？
グコ）は！級、汗日光堅牢度（Ｊ工ＳＬ−θｅｒｒＡ法
アルカリアルカリと非常に良好であった。The dyed products obtained with this dye are uniformly dyed,
In addition, it is extremely thick and has a light fastness (J-Tech SL-〇?).
Guko) ha! The color fastness to sweat and sunlight (J Engineering SL-θerrA method alkali-alkali) was very good.
なお、本実施例で使用したアントラキノン色素は、実施
例／に準じて製造した。Note that the anthraquinone dye used in this example was manufactured according to Example/.
実施例３
第１表に示す本発明のアントラキノン色素（遊離酸の形
で示す。）を実施例／の方法に準じて合成し、実施例／
と同様の方法で綿布を染色したところ、各々均一で濃厚
々染色ができ、また、副光堅牢度！級、汗日光堅牢度７
級といずれも良好であった。Example 3 The anthraquinone dyes of the present invention shown in Table 1 (shown in the form of free acid) were synthesized according to the method of Example/
When cotton fabric was dyed using the same method as above, the dyeing was uniform and deep, and the color fastness to secondary light was also excellent! Grade, sweat and sunlight fastness 7
Both grades were good.
（発明の効果）
本発明の水溶性アントラキノン色素は、新規力青色系の
アントラキノン色素であって、セルロースまたは含窒素
繊維を低温域に於ても良好に染色することができるばか
シでなく、各種堅牢度に優れているという、工業的価値
ある効果を奏するものである。(Effects of the Invention) The water-soluble anthraquinone dye of the present invention is a novel anthraquinone dye with a strong blue color, and is not a simple dye that can dye cellulose or nitrogen-containing fibers well even in a low temperature range. It has an industrially valuable effect of being excellent in fastness.
出 願 人 三菱化成工業株式会社 代 理 人 弁理士 長谷用 − （ほか７名）Sender: Mitsubishi Chemical Industries, Ltd. Representative Patent Attorney Hase - (7 others)
Claims (1)
〕 〔式中、Ｒ＾１は低級アルキレン基を表わし、Ｘはハロ
ゲン原子を表わし、Ｙは−ＯＲ＾２基（但し、ここでＲ
＾２は水酸基、カルボキシル基、スルホン酸基、シアノ
基もしくはハロゲン原子で置換されていてもよい低級ア
ルキル基である）または−Ｏ−（Ｒ＾３Ｏ）−＿ｎＲ＾
４基（但し、ここでＲ＾３は低級アルキレン基、Ｒ＾４
は水酸基で置換されていてもよい低級アルキル基、ｎは
１〜１０の整数である）を表わす〕 で示される水溶性アントラキノン色素。(1) In the form of free acid, the following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・〔I
] [In the formula, R^1 represents a lower alkylene group, X represents a halogen atom, and Y represents an -OR^2 group (however, R
^2 is a hydroxyl group, a carboxyl group, a sulfonic acid group, a cyano group, or a lower alkyl group which may be substituted with a halogen atom) or -O-(R^3O)-_nR^
4 groups (where R^3 is a lower alkylene group, R^4
represents a lower alkyl group which may be substituted with a hydroxyl group, and n is an integer of 1 to 10.] A water-soluble anthraquinone dye represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62085221A JPH0737585B2 (en) | 1987-04-07 | 1987-04-07 | Water-soluble anthraquinone dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62085221A JPH0737585B2 (en) | 1987-04-07 | 1987-04-07 | Water-soluble anthraquinone dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63251474A true JPS63251474A (en) | 1988-10-18 |
| JPH0737585B2 JPH0737585B2 (en) | 1995-04-26 |
Family
ID=13852510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62085221A Expired - Lifetime JPH0737585B2 (en) | 1987-04-07 | 1987-04-07 | Water-soluble anthraquinone dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0737585B2 (en) |
-
1987
- 1987-04-07 JP JP62085221A patent/JPH0737585B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0737585B2 (en) | 1995-04-26 |
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