JPH04198277A - Reactive dye composition and method of dyeing or printing fibrous material by using it - Google Patents
Reactive dye composition and method of dyeing or printing fibrous material by using itInfo
- Publication number
- JPH04198277A JPH04198277A JP2326672A JP32667290A JPH04198277A JP H04198277 A JPH04198277 A JP H04198277A JP 2326672 A JP2326672 A JP 2326672A JP 32667290 A JP32667290 A JP 32667290A JP H04198277 A JPH04198277 A JP H04198277A
- Authority
- JP
- Japan
- Prior art keywords
- reactive dye
- parts
- dyeing
- formula
- alkali
- 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
- 239000000985 reactive dye Substances 0.000 title claims abstract description 35
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 238000004043 dyeing Methods 0.000 title claims description 20
- 238000007639 printing Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 6
- 239000002657 fibrous material Substances 0.000 title abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 18
- 239000003513 alkali Substances 0.000 claims abstract description 8
- 239000000975 dye Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 12
- 230000009471 action Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- 238000002156 mixing Methods 0.000 abstract description 5
- 239000012736 aqueous medium Substances 0.000 abstract description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 abstract description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 1
- XBIPSZHQOHLUPK-UHFFFAOYSA-N 7-amino-2h-naphthalene-1,1,3-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)CC(S(O)(=O)=O)(S(O)(=O)=O)C2=CC(N)=CC=C21 XBIPSZHQOHLUPK-UHFFFAOYSA-N 0.000 abstract 1
- 150000007945 N-acyl ureas Chemical class 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 230000007774 longterm Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000005406 washing Methods 0.000 description 9
- -1 alkali metal salts Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 229920003043 Cellulose fiber Polymers 0.000 description 7
- 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 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000010446 mirabilite Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 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 4
- 239000004952 Polyamide Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 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
- 239000003792 electrolyte Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229920006306 polyurethane fiber Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000004115 Sodium Silicate 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VBQUDDWATQWCPP-UHFFFAOYSA-N ethylsulfonylbenzene Chemical compound CCS(=O)(=O)C1=CC=CC=C1 VBQUDDWATQWCPP-UHFFFAOYSA-N 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 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
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
【発明の詳細な説明】
くM架上の利用分野〉
本発明はヒドロキシル基及び/又はアミド基を含有する
材料、特にセルロースm維、天然又は合成ポリアミド繊
維、ボリウVタン繊維あるいは皮革等、更にはそれらの
混紡繊維を染色及び捺染するに適し、耐光竪牢かつ耐湿
潤竪牢な染色を可能にする改良された反応染料組成物、
並びにその適用に関する。DETAILED DESCRIPTION OF THE INVENTION FIELD OF APPLICATION ON THE MARKET The present invention is applicable to materials containing hydroxyl groups and/or amide groups, particularly cellulose fibers, natural or synthetic polyamide fibers, polyurethane fibers, leather, etc. is an improved reactive dye composition which is suitable for dyeing and printing blended fibers thereof and which enables light-fast and wet-fast dyeing;
and its application.
〈従来の技術ン
ヒドロキシル基及び/又はアミド基を含有する材料の染
色に用いられる反応染料として有用であシ、ビニルスル
ホン系反応基とモノクロルトリアジン系反応基を持つ化
合物は、例えば、特開昭56−15481号公報などに
記載されて公知である。<Conventional technology> Compounds having a vinylsulfone-based reactive group and a monochlorotriazine-based reactive group, which are useful as reactive dyes used for dyeing materials containing hydroxyl groups and/or amide groups, are disclosed in, for example, JP-A No. It is publicly known as described in Japanese Patent No. 56-15481 and the like.
〈発明が解決しようとする課題〉
従来、この種の反応染料は繊維材料の染色及び捺染の分
野に広く使用されている。しかし現在の技術水準は、特
定の染色法に対する適性に関する高い要求水準ならびに
染色物の愁牢性および染色性に関する要求の妬度化の点
から十分に満足すべきものではない。<Problems to be Solved by the Invention> Conventionally, this type of reactive dye has been widely used in the fields of dyeing and printing textile materials. However, the current state of the art is not fully satisfactory in terms of high requirements regarding suitability for specific dyeing methods and increasingly demanding requirements regarding the dullness and dyeability of dyed products.
前記した公知の反応染料も、ビyドアッデ性、溶解性、
経時安定性、及び堅牢性の面で更に改良されることが強
く望まれている。The above-mentioned known reactive dyes also have adhesive properties, solubility,
Further improvements in terms of stability over time and robustness are strongly desired.
本発明者らは、上述の公知染料を改良し、さらに染料に
対して要求される要件を広く満足できる反応染料を見い
出す目的で鋭意検討した結果、本発明を完成した。The present inventors improved the above-mentioned known dyes and completed the present invention as a result of intensive studies aimed at finding a reactive dye that can broadly satisfy the requirements required for dyes.
く課題を解決する為の手段〉
本発明は、遊離酸の形で下記一般式(1)〔式中、Z
バーCH−CHg 又11−CH2CH* Zlを表わ
し、zlはアルカリの作用で脱澄する基を表わす。〕
で示される反応染料と、該染料に対して、1〜80重1
%の、遊離酸の形で、下記一般式(TI)〔式中、Z’
バーCH−CHz 又1d−CH2Ckhz2を表わ
し、zlはアルカリの作用で脱離する基を表わす。〕
で示される反応染料を含有すること?:44> aとす
る反にヌ染料組成物、およびそれを用いることを特徴と
する繊維材料を染色またFi、捺染する方法を提供する
ものである。Means for Solving the Problems> The present invention provides the following general formula (1) [wherein Z
Bar CH-CHg Also represents 11-CH2CH* Zl, where zl represents a group that clears by the action of an alkali. ] The reactive dye represented by 1 to 80 times 1 to the dye
% of the free acid form of the following general formula (TI) [wherein Z'
Bar CH-CHz also represents 1d-CH2Ckhz2, and zl represents a group that is eliminated by the action of an alkali. ] Does it contain the reactive dye indicated by ? :44> In contrast to a, the present invention provides a dye composition and a method for dyeing, printing, and printing fiber materials using the dye composition.
本発明組成物における一般式(f)および(It)で示
される反応染料は、遊離酸の形でまたはその塩の形で存
在し、特にアルカリ金属塩およびアルカリ土類金属塩、
中でもンーダ塩、カリ塩、リチウム塩が好ましho
一般式(1)で示される反応染料は、例えば特開昭56
−15481及びEPC56975に開示の方法に準じ
て製造することができる。The reactive dyes of the general formulas (f) and (It) in the compositions of the invention are present in the form of the free acids or in the form of their salts, in particular alkali metal salts and alkaline earth metal salts,
Among them, powder salts, potassium salts, and lithium salts are preferable.The reactive dye represented by the general formula (1) is, for example,
-15481 and EPC56975.
一般式(II)で示される反応染料は、例えば次のよう
にして製造することができる。水性媒体中で、2−アミ
ツナフタノン−8,6,8−トリスμホン酸を常法でジ
アゾ化し、次いで常法に従って1,8−ジアミノベンゼ
ンとカップリングした後に、シアン酸塩、例えばシアン
酸ソーダなどのシアン酸金属塩を用いてウレイド化をで
示されるモノアゾ化合物を得る。得られたモノアゾ化合
物、塩化シアタμおよび
味を有する。)で示される化合物を任意の順序で縮合し
て、一般式(II)で示される反応染料を製造すること
ができる。前述のウレイド化反応は、好ましくはpH4
〜10に、 さらに好ましくはpH5〜8に調整しなが
ら、好ましくは0〜70℃で、さらに好゛ましくは10
〜40℃で行なうことができる。又、前述の縮合反応は
、水性媒体中、−次的には一10〜50℃で、好ましく
FiO〜30℃で、 pHl〜lOに、好ましくは2〜
7に、1.1 整しながら、二次的には0〜70℃で、
好ましくは10〜50℃で、 PH2〜9に好ましくは
pH8〜6に調整しながら行うことができる。The reactive dye represented by general formula (II) can be produced, for example, as follows. After diazotization of 2-amitunaphthanone-8,6,8-tris-μphonic acid in an aqueous medium in a conventional manner and subsequent coupling with 1,8-diaminobenzene in a conventional manner, a cyanate salt, e.g. A monoazo compound represented by ureidation is obtained using a cyanate metal salt such as . The resulting monoazo compound has theta chloride μ and taste. ) can be condensed in any order to produce a reactive dye represented by general formula (II). The above-mentioned ureidation reaction is preferably carried out at pH 4.
Preferably at 0 to 70° C., more preferably 10 to 10, more preferably 5 to 8.
It can be carried out at ~40°C. The above-mentioned condensation reaction may also be carried out in an aqueous medium, preferably at -10-50°C, preferably at -30°C, and at a pH of 1-10, preferably 2-50°C.
7, 1.1 While adjusting, secondarily at 0-70℃,
It can be carried out preferably at a temperature of 10 to 50°C while adjusting the pH to 2 to 9, preferably 8 to 6.
このようにしてイ4られる一般式(1[)で示される反
応染料は、それ自身ヒドロキシ基含有またはカルボンア
ミド基含有繊維材料の染色または捺染に有用である。The reactive dye represented by the general formula (1) thus obtained is itself useful for dyeing or printing hydroxy group-containing or carbonamide group-containing fiber materials.
本発明の染料組成物は、ασ記一般式(1)および(I
I)で示される反応染料を混合することによって得られ
るものであるが、一般式1r)の反応染料の混合量は、
一般式(1)の反応染料に対して、1〜80重量%、好
ましくは2〜15ii%である。The dye composition of the present invention has general formulas (1) and (I
It is obtained by mixing the reactive dye represented by I), and the amount of the reactive dye represented by the general formula 1r) is as follows:
The amount is 1 to 80% by weight, preferably 2 to 15ii%, based on the reactive dye of general formula (1).
本発明においては、前記一般式(I)および(n)で示
される反応染料は、合成時において、同時に合成される
ことで混合されていてもよく、又、別々に合成されたの
ちに混合されていてもよい。さらには、染色時に混合さ
れても差し支たは力〜ボンアミド基含有材料の染色又は
捺染に使用できる。材料は嘘維材料の形で、あるいはそ
の混紡材料の形で使用されるのが好ましい。In the present invention, the reactive dyes represented by the general formulas (I) and (n) may be mixed by being synthesized at the same time, or may be synthesized separately and then mixed. You can leave it there. Furthermore, even if it is mixed during dyeing, it can be used for dyeing or printing materials containing bonamide groups. Preferably, the material is used in the form of a fibrous material or a blend thereof.
ヒドロキシ基含有材料は天然又は合成ヒドロキシ基含有
材料、たとえばセルロース繊維材料又はその再生−一及
びボリピニアyコー〃などでめる。セルロース繊維材料
は木綿、その他の植物繊維、たとえばリネン、麻、シェ
ード及びフミー繊維が好ましい。再生セルロース繊維は
タトエばビスコース・ステープ〜及びフィラメントビス
コースなどである。The hydroxyl group-containing material may be a natural or synthetic hydroxyl group-containing material, such as cellulose fiber material or its regenerated material and bolipinia yco. Preferably, the cellulosic fibrous material is cotton or other vegetable fibers such as linen, hemp, shade and fumy fibers. Regenerated cellulose fibers include Tatoeba viscose tape and filament viscose.
カルボンアミド晟含有材料はたとえば合成及び天然のポ
リアミド及びポリウレタン、特に繊維の形で、たとえば
羊毛及びその他の動物毛、絹、皮革、ポリアミド−6,
6、ポリアミド−6、ポリアミド−11及びポリアミド
−4などである。Carbonamide-containing materials include, for example, synthetic and natural polyamides and polyurethanes, especially in the form of fibers, such as wool and other animal hairs, silk, leather, polyamide-6,
6, polyamide-6, polyamide-11 and polyamide-4.
本発明化合物は、上述の材料を、特に上述の繊維材料を
、物理的化学的性状に応じた方法で染色又は捺染できる
。The compound of the present invention can dye or print the above-mentioned materials, especially the above-mentioned fiber materials, by a method depending on their physical and chemical properties.
例えば、セルロース繊維上に吸尽染色する場合、炭酸ソ
ーダ、第三燐酸ソーダ、苛性ソーダ等の酸結合剤の存在
下、場合によシ中性填、例えば芒硝又は食塩を加え、所
望によっては、溶解助剤、浸透剤又は均染剤を併用し、
比較的低い温度で行われる。染料O吸尽を促進する中性
塩は、本来の染色温度に達した後に初めて又はそれ以前
に、場合によっては分割して添加できるロ
バジング法に従ってセ/l’ロース繊維を染色する場合
、室温又は高められた温度でバッドし乾燥後、スチーミ
ング又は乾熱によりて固着できる。For example, when exhaust dyeing is carried out on cellulose fibers, in the presence of an acid binder such as soda carbonate, sodium phosphate or caustic soda, optionally a neutral filler, such as mirabilite or common salt, is added and, if desired, dissolved. Using auxiliary agents, penetrants or leveling agents together,
It is carried out at relatively low temperatures. Neutral salts that promote dye O exhaustion can be added at room temperature or at room temperature when dyeing c/l' loin fibers according to the robbing method, which can optionally be added in portions only after or before the original dyeing temperature is reached. After buffing and drying at elevated temperatures, it can be fixed by steaming or dry heat.
セルロース繊維に対して捺染を行う場合、−相で、例え
ば′ILIM又はその他の酸結合剤を含有する捺染ペー
ストで印捺し、次いで100〜160℃でスチーミング
することによって、あるいは二相で、例えば中性又は弱
酸性捺染ペーストで捺染し、これを熱い電解質含有アル
カリ性浴に通過させ、又はアルカリ性電解質含有バジン
グ液でオーバーバジングし、スチーミング又は乾熱処理
して実施できる。When printing is carried out on cellulose fibers, it can be carried out in one phase, e.g. by printing with a printing paste containing 'ILIM or other acid binders and then steaming at 100-160°C, or in two phases, e.g. Printing can be carried out by printing with a neutral or weakly acidic printing paste, passing it through a hot alkaline bath containing an electrolyte, or overbagging with a bagging liquid containing an alkaline electrolyte, followed by steaming or dry heat treatment.
捺染ペーストには、例えばアルギン酸ソーダ又は澱粉エ
ーテルのような糊剤又は乳化剤が、所望によっては、例
えば尿素のよ5な通常の捺染助剤かつ(又は)分散剤と
併用して用いられる。In the printing pastes, thickening agents or emulsifiers, such as, for example, sodium alginate or starch ethers, are used, if desired, in combination with customary printing auxiliaries and/or dispersants, such as, for example, urea.
セルロース繊維上に本発明の染料組成物を固着させるに
適した酸結合剤は、例えばアルカリ金属又はアルカリ土
類金属と無機又は有機酸あるいは加熱状態でアルカリ遊
離する化合物との水溶性塩基性塩である。特にアルカリ
金属の水酸化物及び弱ないし中程度の強さの無機又は有
機酸のアルカリ金属塩が拳げられ、その内、特にソーダ
塩及びカリ塩が好ましい。このような酸結合剤として、
例えば苛性ソーダ、苛性カリ、重曹、炭酸ソーダ、蟻酸
ソーダ、炭酸カリ、第一、第二又は第三燐酸ソーダ、ケ
イ酸ソーダ、トリクロロ酢酸ソーダ等が挙げられる。Suitable acid binders for fixing the dye compositions of the invention on cellulose fibers are, for example, water-soluble basic salts of alkali metals or alkaline earth metals with inorganic or organic acids or compounds which liberate alkali when heated. be. Particularly preferred are alkali metal hydroxides and alkali metal salts of weak to medium strength inorganic or organic acids, of which soda salts and potassium salts are particularly preferred. As such an acid binder,
Examples include caustic soda, caustic potash, baking soda, soda carbonate, sodium formate, potassium carbonate, primary, secondary or tertiary sodium phosphate, sodium silicate, sodium trichloroacetate and the like.
合成及び天然のポリアミド及びポリウレタン繊維の染色
は、まず酸性ないし弱酸性の染浴からμ■値の制御下に
吸尽させ、次に固着させるため中性、場合によジアルカ
リ性のpH値に変化させることによって行える。染色は
通常60〜120℃の温度で行えるが、均染性を達成す
るために通常の均染剤、例えば塩化シアタμと8倍モル
のアミノベンゼンスルホン酸又はアミンナフタレンスル
ホン酸との縮合生成物あるいd 例、t ld’ステア
リルアミンとエチレンオキサイドとの付加生成物を用い
ることもできる。The dyeing of synthetic and natural polyamide and polyurethane fibers involves first exhaustion under control of the μ■ value from an acidic or slightly acidic dye bath, and then a change to a neutral or sometimes dialkaline pH value for fixation. This can be done by letting Dyeing can usually be carried out at a temperature of 60 to 120°C, but in order to achieve level dyeing properties, conventional leveling agents, such as a condensation product of theata μ chloride and 8 times the mole of aminobenzenesulfonic acid or amine naphthalenesulfonic acid, are used. Alternatively, an addition product of stearylamine and ethylene oxide can also be used.
本発明の染料組成物繊維材料に対する染色及び捺染にお
いて優れた性能を発揮する点に特徴がある。特にセルロ
ース繊維材料の染色に好適であシ、良好な耐光性と附汗
日光性、耐湿潤性、たとえば耐洗濯性、耐過酸化洗濯性
、耐汗性、#塩素性、耐酸加水分解性及び耐アルカル性
、更に良好な耐摩擦性と耐アイロン性を有する。The dye composition of the present invention is characterized in that it exhibits excellent performance in dyeing and printing fiber materials. It is particularly suitable for dyeing cellulose fiber materials, and has good light fastness, perspiration and sunlight resistance, moisture resistance, such as washing resistance, peroxidation washing resistance, sweat resistance, chlorine resistance, acid hydrolysis resistance and It has alkali resistance, as well as good abrasion resistance and ironing resistance.
また優れたビルドアツプ性、溶解性、均染性及びウオツ
シュオフ性、さらに良好な吸尽・固着性を有する点、染
色温度や染浴此の変動による影暢を受けにくく安定した
品質の染色物が得られる点において特徴を有する。In addition, it has excellent build-up properties, solubility, level dyeing properties, and wash-off properties, as well as good exhaustion and fixation properties, and dyed products with stable quality that are less affected by fluctuations in dyeing temperature and dye bath. It is characterized by the fact that it is
また、得られた染色物のフィックス処理時や樹脂加工時
における変色が少なく、保存時の塩基性物質との接触に
よる変化が少ないことも特徴である。Another characteristic of the dyed product is that there is little discoloration during fix treatment or resin processing, and there is little change due to contact with basic substances during storage.
以下、実施例によυ本発明の詳細な説明する。Hereinafter, the present invention will be explained in detail with reference to Examples.
例中、部および%は夫々M旦部および左jk%を表わす
。In the examples, part and % represent Mdan part and left jk%, respectively.
実施例 l
遊離酸の形で、下記構造式(1)
で示されるモノアゾ反応染料100部と遊離酸の形で下
記構造式(1)
で示されるモノアゾ反応染料10部とを配合して反応染
料組成物を得た。その0.1.0.8および0.6部を
、各々水200部に溶解し、芒硝10部と木mlO部を
加え、60℃に昇温し、次酸ソーダ4部を加えて、1時
間染色した。水洗、ソーピング、水洗そして乾燥を行な
い、各々諸盟牢度に優れ、良好なビルドアツプ性を有す
る黄色の染色物が得られた。Example 1 A reactive dye was prepared by blending 100 parts of a monoazo reactive dye represented by the following structural formula (1) in the form of a free acid with 10 parts of a monoazo reactive dye represented by the following structural formula (1) in the form of a free acid. A composition was obtained. 0.1, 0.8 and 0.6 parts of each were dissolved in 200 parts of water, 10 parts of Glauber's salt and mlO of wood were added, the temperature was raised to 60°C, 4 parts of sodium hypochlorite was added, and 1 Time stained. After washing with water, soaping, washing with water and drying, a yellow dyed product having excellent tenacity and good build-up properties was obtained.
上記式(8)で示されるモノアゾ反応染料は以下のよう
にして製造した。The monoazo reactive dye represented by the above formula (8) was produced as follows.
2−アミノアフタレン−8,6,8−)リスルホン酸8
8.8部を水中、常法でジアゾ化した後K、1.8−ジ
アミノベンゼン10.8部’t−7Jtlえて常法にて
カップリンし、シアン酸ナトリウム7.15部を加えて
、2NのMCI水溶液を用いてpHγに@整しながら室
温化でウレイド化を終了せしめ、塩化シアヌlv1g、
5部を加えて第−縮合全行ない続いて1−アミノ−3−
β−ス〜ファートエチルスルホニルベンゼン28.1部
を加えて第二縮合を終了させた後、単離して前記の構造
式(II)で示される反応染料を得た。2-Aminoaphthalene-8,6,8-)lysulfonic acid 8
After diazotizing 8.8 parts in water in a conventional manner, adding 10.8 parts of K, 1,8-diaminobenzene and coupling in a conventional manner, adding 7.15 parts of sodium cyanate, The ureidation was completed at room temperature while adjusting the pH to γ using a 2N MCI aqueous solution, and 1 g of cyanuric chloride was added.
Complete the first condensation by adding 5 parts of 1-amino-3-
After the second condensation was completed by adding 28.1 parts of β-sulfate ethylsulfonylbenzene, the reaction dye represented by the structural formula (II) was obtained by isolation.
実施例 2
実施例1で用いた、構造式(1)で示されるモノアゾ反
応染料100部と実施例1で用いた、構造式(1)で示
される七ノアゾ反応染料5部とを配合して得た染料組成
物0.1.0.8および0.6部を、各4水200部に
溶解し、芒硝10部と木綿10部を加え、60℃に外温
し、炭酸ソーダ4部を加えて、1時間染色した。水洗、
ソーピング、水洗そして乾燥を行ない、各々諸堅牢度に
優れ、良好なビルドアツプ性を有する黄色の染色物が得
られ九。Example 2 100 parts of the monoazo reactive dye represented by the structural formula (1) used in Example 1 and 5 parts of the heptanoazo reactive dye represented by the structural formula (1) used in Example 1 were blended. 0.1, 0.8 and 0.6 parts of the obtained dye compositions were each dissolved in 200 parts of water, 10 parts of Glauber's salt and 10 parts of cotton were added, the mixture was heated to 60°C, and 4 parts of soda carbonate was added. In addition, staining was carried out for 1 hour. washing with water,
After soaping, rinsing and drying, a yellow dyed product with excellent fastness and good build-up properties was obtained.
実施例 8
遊離酸の形で下記構造式(1)
で示されるモノアゾ反応染料100部と遊離酸の形で下
肥構造式(IV )
Cj2 (1,)
で示されるモノアゾ反応染料10部とを配合して得た染
料組成物0.1.0.8および0.6部を、各々水20
0部に溶解し、芒硝10部と木綿10部を加え、60℃
に昇温し、I#酸ソーダ4部を加えて、1時間染色した
。水洗、ソーピング、水洗そして乾燥を行ない、各々諸
堅牢度に優れ、良好なビルドアツプ性を有する黄色の染
色物が得られた。Example 8 100 parts of a monoazo reactive dye represented by the following structural formula (1) in the form of a free acid and 10 parts of a monoazo reactive dye represented by the following structural formula (IV) Cj2 (1,) in the form of a free acid were prepared. 0.1, 0.8 and 0.6 parts of the dye composition obtained by blending were added to 20 parts of water, respectively.
0 parts, add 10 parts of Glauber's salt and 10 parts of cotton, and heat at 60°C.
4 parts of I# acid soda were added and dyed for 1 hour. After washing with water, soaping, washing with water and drying, a yellow dyed product with excellent fastness and good build-up properties was obtained.
実施例 4
遊離酸の形で下記構造式(V)
で示されるモノアゾ染料100部と遊離酸の形で下記−
形成(vl )
で示される七ノアゾ反応染@5部とを配合して得た染料
組成物0.1.0.8および0.6部を、各々水200
部に溶解し、芒硝10部と木綿10部を加え、60℃に
外温し、炭酸ソーダ4部を加えて、1時間染色した。水
洗、ソーピング、水洗そして乾燥を行ない、各々諸堅牢
度に優れ、良好なビルドアツプ性を有する黄色の染色物
が得られた。Example 4 100 parts of a monoazo dye represented by the following structural formula (V) in the form of a free acid and the following -
Formation (vl) 0.1, 0.8 and 0.6 parts of the dye compositions obtained by blending with 5 parts of heptanoazo reactive dye were added to 200 parts of water, respectively.
10 parts of Glauber's salt and 10 parts of cotton were added to the solution, heated externally to 60°C, added 4 parts of soda carbonate, and dyed for 1 hour. After washing with water, soaping, washing with water and drying, a yellow dyed product with excellent fastness and good build-up properties was obtained.
実施例 5
実施例1−4で用いた、各々の反応染料組成物を用いて
、以下の組成を持つ、色糊を作った。Example 5 Using each of the reactive dye compositions used in Examples 1-4, colored pastes having the following compositions were made.
反応染料組成物 5部尿米
5部アノンギン酸ソーダ(5%
)元糊 50部(、p ン1
25 部重o′
2部
バランス 13部この色糊を
シルケット加工線ブロード上に印捺し、中tiIJ乾燥
後、100℃で5分間スチーミングを行い、湯洗い、ソ
ーピング、湯洗いそして乾燥した。得られた捺染物は、
いずれも諸堅牢度に優れ、良好なビルドアップ18Eを
有していたO
(以下余白)Reactive dye composition 5 parts urine rice
5 parts Sodium anongate (5%
) Motonori 50 parts (, p n1
25 Part weight o'
2 parts Balance 13 parts This colored paste was printed on broad mercerized wire, dried in medium tiIJ, steamed at 100° C. for 5 minutes, washed with hot water, soaped, washed with hot water and dried. The obtained printed material is
All of them had excellent fastness and good build-up 18E (margins below)
Claims (2)
Z_1を表わし、Z_1はアルカリの作用で脱離する基
を表わす。〕 で示される反応染料と、該染料に対して、1〜80重量
%の、遊離酸の形で、下記一般式▲数式、化学式、表等
があります▼ 「式中、Z′は−CH=CH_2又は−CH_2CH_
2Z_2を表し、Z_2はアルカリの作用で脱離する基
を表わす。〕 で示される反応染料を含有することを特徴とする反応染
料組成物。(1) In the form of a free acid, there is the following general formula ▲ Numerical formula, chemical formula, table, etc. ▼ “In the formula, Z is -CH=CH_2 or -CH_2CH_2
Z_1 represents a group that is eliminated by the action of an alkali. ] The following general formula ▲ Numerical formulas, chemical formulas, tables, etc. are available for the reactive dye represented by and 1 to 80% by weight of the dye in the form of free acid. ▼ "In the formula, Z' is -CH= CH_2 or -CH_2CH_
2Z_2, where Z_2 represents a group that is eliminated by the action of an alkali. ] A reactive dye composition characterized by containing a reactive dye represented by the following.
する繊維材料の染色または捺染方法。(2) A method for dyeing or printing textile materials, which comprises using the reactive dye composition according to claim 1.
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2326672A JP2949838B2 (en) | 1990-11-27 | 1990-11-27 | Reactive dye composition and method for dyeing or printing fiber material using the same |
GB9122611A GB2250297B (en) | 1990-11-27 | 1991-10-24 | Fiber reactive yellow dye composition |
AU86814/91A AU642542B2 (en) | 1990-11-27 | 1991-10-28 | Triazine fiber reactive yellow dye composition |
US07/794,217 US5308362A (en) | 1990-11-27 | 1991-11-19 | Fiber reactive yellow dye composition |
DE4138084A DE4138084C2 (en) | 1990-11-27 | 1991-11-19 | Yellow fiber reactive dye composition |
ITRM910886A IT1249731B (en) | 1990-11-27 | 1991-11-22 | YELLOW REACTIVE COLORING COMPOSITION TOWARDS FIBERS |
BE9101077A BE1006310A3 (en) | 1990-11-27 | 1991-11-22 | Composition of dye reactive yellow fiber. |
CH3438/91A CH683265A5 (en) | 1990-11-27 | 1991-11-25 | Yellow fiber reactive dye composition. |
PL91292525A PL168215B1 (en) | 1990-11-27 | 1991-11-25 | Composition of reactive dyes and method of dyeing or printing fibrous materials or leather |
CS913582A CS358291A3 (en) | 1990-11-27 | 1991-11-26 | Yellow reactive composition for fibers dyeing |
ES9102627A ES2036487B1 (en) | 1990-11-27 | 1991-11-26 | COMPOSITION OF YELLOW MONOAZOIC DYE, REACTIVE, TO HAVE OR STAMP FIBROUS MATERIALS OR LEATHER AND CORRESPONDING METHOD. |
KR1019910021380A KR960011059B1 (en) | 1990-11-27 | 1991-11-27 | Reactive dye composition |
TR91/1136A TR25947A (en) | 1990-11-27 | 1991-12-26 | REACTIVE YELLOW PAINT COMPOSITION AGAINST FIBER. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2326672A JP2949838B2 (en) | 1990-11-27 | 1990-11-27 | Reactive dye composition and method for dyeing or printing fiber material using the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH04198277A true JPH04198277A (en) | 1992-07-17 |
JP2949838B2 JP2949838B2 (en) | 1999-09-20 |
Family
ID=18190377
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2326672A Expired - Lifetime JP2949838B2 (en) | 1990-11-27 | 1990-11-27 | Reactive dye composition and method for dyeing or printing fiber material using the same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2949838B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008545844A (en) * | 2005-05-30 | 2008-12-18 | ダイスター・テクスティルファルベン・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・ドイッチュラント・コマンデイトゲゼルシャフト | Reactive dyes, their preparation and their use |
-
1990
- 1990-11-27 JP JP2326672A patent/JP2949838B2/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008545844A (en) * | 2005-05-30 | 2008-12-18 | ダイスター・テクスティルファルベン・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・ドイッチュラント・コマンデイトゲゼルシャフト | Reactive dyes, their preparation and their use |
Also Published As
Publication number | Publication date |
---|---|
JP2949838B2 (en) | 1999-09-20 |
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