JPS63101458A - Water-soluble monoazo compound and method of dyeing and printing fibrous material by using the same - Google Patents
Water-soluble monoazo compound and method of dyeing and printing fibrous material by using the sameInfo
- Publication number
- JPS63101458A JPS63101458A JP61248201A JP24820186A JPS63101458A JP S63101458 A JPS63101458 A JP S63101458A JP 61248201 A JP61248201 A JP 61248201A JP 24820186 A JP24820186 A JP 24820186A JP S63101458 A JPS63101458 A JP S63101458A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- monoazo compound
- independently
- acid
- 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 monoazo compound Chemical class 0.000 title claims description 23
- 238000004043 dyeing Methods 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 13
- 239000002657 fibrous material Substances 0.000 title description 4
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 10
- 239000003513 alkali Substances 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 4
- 239000000835 fiber Substances 0.000 abstract description 12
- 239000000975 dye Substances 0.000 abstract description 9
- 150000001412 amines Chemical class 0.000 abstract 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 abstract description 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical group ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract description 5
- 229920003043 Cellulose fiber Polymers 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 4
- 229920002647 polyamide Polymers 0.000 abstract description 4
- 238000005859 coupling reaction Methods 0.000 abstract description 3
- 239000010985 leather Substances 0.000 abstract description 3
- 230000007935 neutral effect Effects 0.000 abstract description 3
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 abstract description 2
- 229920006306 polyurethane fiber Polymers 0.000 abstract description 2
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 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 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910052911 sodium silicate 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
- 238000003756 stirring Methods 0.000 description 2
- 210000004243 sweat Anatomy 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
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- DBGSRZSKGVSXRK-UHFFFAOYSA-N 1-[2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]acetyl]-3,6-dihydro-2H-pyridine-4-carboxylic acid Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CCC(=CC1)C(=O)O DBGSRZSKGVSXRK-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- 240000008564 Boehmeria nivea Species 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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 241000134884 Ericales Species 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
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- 239000002994 raw material Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride 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
- 229940080313 sodium starch Drugs 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer 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
- 239000007858 starting material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 238000004804 winding Methods 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、ヒドロキシ基及び／又はカルボンア【ド基含
有材料、特にセルロース繊維、天然又は合成ポリアミド
繊維、ポリウレタン繊維あるいは皮革等、あるいはそれ
らの混紡ａ紬を染色及び捺染するのに有用な水溶性モノ
アゾ化合物並びにその適用に関するものである。Detailed Description of the Invention <Industrial Application Field> The present invention is directed to materials containing hydroxy groups and/or carbon oxide groups, particularly cellulose fibers, natural or synthetic polyamide fibers, polyurethane fibers, leather, etc., or blends thereof. This invention relates to a water-soluble monoazo compound useful for dyeing and printing pongee and its application.
〈従来の技術〉
反応染料は、各種の染色方法を適用することができ、鮮
明な色相、染色物が良好な湿潤堅牢度を持つ等の特徴を
有するためセルロース系繊維、ポリアミド系繊維の浸染
、捺染用として広く用いられてきている。しかし、濃厚
な染色物を得る目的で反応染料を使用した場合、従来の
染料では充分な染着性を有していないため染色効率の低
下現象が多く認められ、染色コスト、廃水処理の点など
からさらにレベルアップを望まれている。<Prior art> Reactive dyes can be applied to various dyeing methods and have characteristics such as clear hues and good wet fastness of dyed products, so they are used for dyeing cellulose fibers and polyamide fibers, It has been widely used for textile printing. However, when using reactive dyes for the purpose of obtaining richly dyed products, conventional dyes do not have sufficient dyeing properties, resulting in a decrease in dyeing efficiency, resulting in problems such as dyeing costs and wastewater treatment. It is hoped that the level will improve further.
〈発明が解決しようとする問題点〉
本発明者らは、諸堅牢度、均染性、水溶性等の種々の染
料特性に優れかつ良好な染着性を有する染料を見い出す
ことを目的に鋭意研究を行なった結果、特定の但金物が
目的とする性能を有することを見い出した。<Problems to be Solved by the Invention> The present inventors have worked diligently with the aim of finding a dye that is excellent in various dye properties such as fastness, level dyeing property, and water solubility, and has good dyeing properties. As a result of research, it was discovered that a specific metal material had the desired performance.
く問題を解決するための手段〉
本発明は、遊離酸の形で下記一般式（Ｉ）Ｒ１
〔式中、Ｒ，、Ｒ，及びＲ８は互いに独立に水素原子又
は置換されてもよい低級アルキル基を示しＢ、 、 Ｂ
２は互いに独立にメチル基、メトキシ基、エチル基、エ
トキシ基、塩素原子、臭素原子、スルホン酸又はカルボ
ン酸基によって置換されてもよいフェニレン基、または
スルホン酸基で置換されてもよいナフチレン基を示す。[Means for Solving the Problem] The present invention provides a free acid having the following general formula (I) R1 [wherein R, R, and R8 are each independently a hydrogen atom or an optionally substituted lower alkyl Indicates the group B, , B
2 is a phenylene group which may be independently substituted with a methyl group, a methoxy group, an ethyl group, an ethoxy group, a chlorine atom, a bromine atom, a sulfonic acid or a carboxylic acid group, or a naphthylene group which may be substituted with a sulfonic acid group; shows.
Ｙｏ及びＹ、は互いに独立に−ＣＨ＝ＣＨ１又は、−Ｃ
Ｈ，ＣＨ，Ｚを示し、ここにＺはアルカリの作用で脱離
する基を示す。ｍ及びｎは０又は１を表わす。〕
で表わされる水溶性モノアゾ化合物及びそれを用いてヒ
ドロキシ基又は／及びカルボンアミド基含有材料を染色
又は捺染する方法を提供する。Yo and Y are each independently -CH=CH1 or -C
It represents H, CH, and Z, where Z represents a group that is eliminated by the action of an alkali. m and n represent 0 or 1. ] Provided are a water-soluble monoazo compound represented by the following and a method for dyeing or printing a material containing a hydroxyl group or/and a carbonamide group using the water-soluble monoazo compound.
一般式（１）において、Ｒ１ｅ Ｒｇ及びＲ，が互いに
独立に置換されていてもよい低級アルキル基である場合
、その様な基としては例えば特開昭５９−１２２５４９
号公報に示された基が該当し、好ましくはメチル基及び
エチル基である。またＲＩｔＲ，の少なくとも一方は水
素原子であることがより好適であり、Ｒ１は水素原子あ
るいはメチル基であることが好ましい。In general formula (1), when R1e Rg and R are lower alkyl groups which may be independently substituted, examples of such groups include those described in JP-A-59-122549.
The groups shown in the above publication are applicable, and methyl and ethyl groups are preferred. Further, it is more preferable that at least one of RItR is a hydrogen atom, and R1 is preferably a hydrogen atom or a methyl group.
に示された基が相当するが、その内Ｂ、 、 Ｂ！が互
いに独立にメチル基又はメトキシ基で置換されてもよい
フェニレン基であることが好ましい。The groups shown in are equivalent, among which B, , B! are preferably phenylene groups which may be independently substituted with a methyl group or a methoxy group.
Ｙ１又ハＹ！カ、−ＣＨＩＣＭ、Ｚ テアル場合（７）
Ｚ Ｊ！、アルカリの作用で脱離能がある基であり、
例えば、硫酸エステル基、チオ硫酸エステル基、リン酸
エステル基、ハロゲン原子等が挙げられる。Y1mataha Y! Ka, -CHICM, Z theal case (7)
Z J! , is a group that has the ability to be eliminated by the action of an alkali,
Examples include a sulfate ester group, a thiosulfate ester group, a phosphate ester group, and a halogen atom.
好ましいＹｌ及びＹ２は共にβ−スルフアートエチルの
場合であり、その中に一部ビニルが混在していてもよい
。Both Yl and Y2 are preferably β-sulfatoethyl, and some vinyl may be mixed therein.
前記一般式（Ｉ）において特に好ましいモノアゾ化合物
は、遊ｍ酸の形で下記一般式（１１）及び（Ｉｌｌ）〔
式中、Ｒ４は水素原子、メチル基又はエチル基を示す。Particularly preferable monoazo compounds in the general formula (I) are those represented by the following general formulas (11) and (Ill) in the form of free acids.
In the formula, R4 represents a hydrogen atom, a methyl group or an ethyl group.
〕
〔式中、Ｒ，は水素原子、メチルシζ又はエチル基を示
す。〕
で示されるモノアゾ化合物である。] [In the formula, R represents a hydrogen atom, methyloxyζ or an ethyl group. ] It is a monoazo compound shown by.
これらのモノアゾ化合物は、アルカリ金属又はアルカリ
土類金属の塩であることが好ましく、特にナトリウム又
はカリウム塩が好ましい。These monoazo compounds are preferably salts of alkali metals or alkaline earth metals, particularly sodium or potassium salts.
本発明化合物は例えば次のようにして製造することがで
きる。一般式（ＩＶ）
Ｈ
〔式中、Ｒ３、ｎは前記の意味を有する。〕で示される
ア【ノナフタレンスルホン酸と塩化シアヌルと一次的に
縮合させ、この−成縮合物に、一般式（Ｖ）
〔式中、ｍは前記の意味を有する。〕
で示されるアニリンスルホン酸を通常の方法でジアゾ化
したジアゾニウム化合物を加えて中性ないしアルカリ性
でカップリングさせることで一般式（Ｖｌ）
〔式中、ｍ、ｎは前記の意味を有する。〕で示されるモ
ノアゾ化合物を得、これに下記一般式（Ｖｌ）、（■）
〔式中、Ｒ１，Ｒ，、Ｂ、 、 Ｂ、 、 Ｙ、及びＹ
、は前記の意味を有する。〕
で示されるアミンを二次的、三次的に任意の順序で縮合
させて一般式（１）の化合物を得ることができる。The compound of the present invention can be produced, for example, as follows. General formula (IV) H [wherein R3 and n have the above-mentioned meanings. A [nonaphthalene sulfonic acid and cyanuric chloride] are firstly condensed, and this condensate is formed by the general formula (V) [where m has the above-mentioned meaning. ] By adding a diazonium compound obtained by diazotizing the aniline sulfonic acid represented by the above in a conventional manner and coupling in neutral or alkaline conditions, the general formula (Vl) [wherein m and n have the above-mentioned meanings] is obtained. ] was obtained, and the monoazo compound represented by the following general formula (Vl), (■) [wherein, R1, R,, B, , B, , Y, and Y
, has the above meaning. ] The compound represented by the general formula (1) can be obtained by condensing the amines represented by the formula (1) in any order in a secondary or tertiary manner.
上記の出発化合物は、反応条件次第で酸及び／又は塩、
特にアルカリ金属塩又はアルカリ土類金属塩の形で使用
される。The above starting compounds can be acids and/or salts, depending on the reaction conditions.
In particular they are used in the form of alkali metal or alkaline earth metal salts.
本発明により製造したモノアゾ化合物は、場合によって
は無機塩を除去し、必要に応じて安定剤もしくは染色性
改良剤の添加を行い液状品とすることもでき、あるいは
この液状品または反応溶液を蒸発、たとえば噴霧乾燥に
より粉体品とすることもでき、さらに一般に公知の方法
。The monoazo compound produced according to the present invention can be made into a liquid product by removing inorganic salts and adding stabilizers or dyeability improvers as necessary, or the liquid product or reaction solution can be evaporated. , for example by spray-drying, as well as methods known in general.
により電解質の添加による塩析分離を経て、液状品また
は粉体品とすることもできる。It can also be made into a liquid or powdered product through salting out separation by adding an electrolyte.
本発明によるモノアゾ化合物は、繊維反応性染料として
利用でき、繊維材料、たとえばヒドロキシ基またはカル
ボン酸アミド基含有材料を染色できる。The monoazo compounds according to the invention can be used as fiber-reactive dyes and can dye textile materials, for example materials containing hydroxy groups or carboxylic acid amide groups.
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生成物
及びポリビニルアルコールである。セルロース繊維材料
は木綿、しかもその他の植物ａ維、たとえばリネン、麻
、ジュート及びラミー繊維が好ましい。再生セルロース
ａ維はたとえばビスコース・ステーブル及びフィラメン
トビスコースである。Hydroxy group-containing materials are natural or synthetic hydroxy group-containing materials, such as cellulose fiber materials or their regenerated products and polyvinyl alcohol. The cellulosic fiber material is preferably cotton, but also other vegetable fibers such as linen, hemp, jute and ramie fibers. Regenerated cellulose a-fibers are, for example, viscose stable and filament viscose.
カルボンアミド基含有材料はたとえば合成及び天然ポリ
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である。Materials containing carbonamide groups are, 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-
It is 4.
染色は繊維反応性染料の反応性基に応じた方法を適用で
きる。For dyeing, methods depending on the reactive group of the fiber-reactive dye can be applied.
例えば、セルローズ系繊維の場合、本発明染料と酸結合
剤、例えば苛性ソーダ、炭酸ナトリウム、燐酸塩、珪酸
塩又は炭酸水素ナトリウムを用いて染色を行う。染色方
法は、繊維の性質、及び物理的形状によって選択でき、
ｔことえば吸尽法、捺染法又はコールドパッド−バッチ
−アップ法等を採用できる。For example, in the case of cellulosic fibers, dyeing is carried out using the dye according to the invention and an acid binder such as caustic soda, sodium carbonate, phosphate, silicate or sodium bicarbonate. The dyeing method can be selected depending on the properties and physical shape of the fiber.
For example, an exhaustion method, a textile printing method, a cold pad batch-up method, etc. can be employed.
吸尽法の場合、炭酸ナトリウム、第三燐酸ナトリウム、
苛性ソーダ等の酸結合剤の存在下に芒硝又は食塩を加え
た染浴で比較的低い温度で行われる。捺染法の場合、例
えばアルギン酸ナトリウム又は澱粉エーテルのような潮
料又は乳化潮料及び炭酸ナトリウム、炭酸水素ナトリウ
ム、苛性ソーダ、第三燐酸ナトリウム、トリクロル酢酸
ナトリウム又は相当するカリウムもしくはアルカリ土類
化合物のようなアルカリ性又はアルカリを放出する薬剤
とともに、所望によっては、例えば尿素のような通常の
捺染助剤又は分散剤の添加のもとに繊維上に施し、乾燥
し、そして特に水蒸気の存在下で熱処理に付すことによ
り染色できる。コールド−バッチ−アップ染色の場合、
酸結合剤として苛性ソーダ単独、あるいは珪酸ソーダ、
炭酸ナトリウム又は第三燐酸ナトリウムを併用し、場合
によっては、芒硝又は食塩を加えて、所望によっては尿
素などの溶屏助剤あるいは浸透剤の添加のもとに常温付
近で、繊維上にパッドし、ロールに巻き上げ、８時間な
いし一夜問おない後に水洗し、乾燥することにより染色
できる。In the case of exhaustion method, sodium carbonate, trisodium phosphate,
It is carried out at relatively low temperatures in a dye bath containing mirabilite or common salt in the presence of an acid binder such as caustic soda. In the case of printing processes, salt or emulsified salts such as sodium alginate or starch ethers and salts such as sodium carbonate, sodium bicarbonate, caustic soda, sodium triphosphate, sodium trichloroacetate or the corresponding potassium or alkaline earth compounds are used. applied to the fiber together with an alkaline or alkali-releasing agent, optionally with the addition of customary printing aids or dispersants, such as urea, dried and subjected to heat treatment, especially in the presence of water vapor. It can be dyed by For cold-batch-up staining,
Caustic soda alone or sodium silicate as an acid binder,
It is padded onto the fibers using sodium carbonate or trisodium phosphate, optionally with the addition of Glauber's salt or salt, and optionally with the addition of a solubilizing agent or penetrating agent such as urea, at room temperature. It can be dyed by winding it up into a roll, leaving it for 8 hours or overnight, washing it with water, and drying it.
本発明化合物は繊維材料に対して優れた性能を発揮する
点に特徴があり、特にセルロース系ｋａ雑に対する染色
に好適である。高い吸尽率と固着率、優れたビルドアツ
プ性を示すことに顕著な特徴を有する。さらに均染性及
び易洗浄性を示し、温度、浴比、塩濃度等の染色条件に
多少の変動が生じても染色性への影響がほとんどない等
の特徴を合わせて有している。また耐光性、汗耐光性、
耐汗性、耐酸加水分解性、耐洗濯性、耐塩素性などの諸
堅牢度にも優れている。The compound of the present invention is characterized in that it exhibits excellent performance on fiber materials, and is particularly suitable for dyeing cellulose-based materials. It is notable for its high exhaustion rate, high fixation rate, and excellent build-up performance. Furthermore, it exhibits level dyeing properties and easy cleaning properties, and has the characteristics that dyeing properties are hardly affected even if there are slight variations in dyeing conditions such as temperature, bath ratio, salt concentration, etc. In addition, light resistance, sweat resistance,
It also has excellent fastness properties such as sweat resistance, acid hydrolysis resistance, washing resistance, and chlorine resistance.
次に本発明を実施例によって説明する。Next, the present invention will be explained by examples.
文中、部は重量部を表わす。In the text, parts represent parts by weight.
実施例１
塩化シアヌル７．４部を水５０部中に分散させ、この中
に６−ア【ノー１−ヒドロキシナフタレン−８−スルホ
ン酸９．８部の中性水溶液１００部を加えて、θ〜６°
Ｃ，ｐＨ２〜４にて原料の６−アミノ−１−ヒドロキシ
ナフタレン−８−スルホン酸が認められなくなるまで撹
拌を続ける。このようにして得た第一縮合物質の溶液中
にｐ−アニシジン−ｍ−スルホン酸９．０部を公知の方
法でジアゾ化した液を加えてｐＨ８〜８．１０〜１６°
Ｃにてカップリングを行なう。反応終了後、Ｎ−エチル
アニリン−８−β−スルファートエチルスルホ２１３．
６部を加えてｐＨ４〜６．８０〜５０℃で第２縮合を行
ない続いて、１−アミノベンゼン−８−β−スルフアー
トエチルスルホン８４部を加えて同ｐＨ，５０〜７０℃
にて第８縮合を行なう。反応終了後、塩化カリウムを加
えて塩析し、−過洗浄後、乾燥し遊離酸の形で下記構造
のモノアゾ化合物８０部を得た。Example 1 7.4 parts of cyanuric chloride was dispersed in 50 parts of water, and 100 parts of a neutral aqueous solution of 9.8 parts of 6-a[no-1-hydroxynaphthalene-8-sulfonic acid] was added thereto. ~6°
C, stirring was continued at pH 2 to 4 until the raw material 6-amino-1-hydroxynaphthalene-8-sulfonic acid was no longer observed. A solution obtained by diazotizing 9.0 parts of p-anisidine-m-sulfonic acid by a known method was added to the solution of the first condensate obtained in this manner, and the pH was adjusted to 8-8.10-16°.
Coupling is performed at C. After completion of the reaction, N-ethylaniline-8-β-sulfate ethyl sulfo 213.
6 parts of 1-aminobenzene-8-β-sulfatoethyl sulfone were added and the mixture was heated to pH 4-6. Second condensation was carried out at 80-50°C.
The eighth condensation is carried out at . After the reaction was completed, potassium chloride was added for salting out, followed by excessive washing and drying to obtain 80 parts of a monoazo compound having the following structure in the form of a free acid.
実施例２
実施例１と同様な方法で、塩化シアヌルと第一縮合を行
なうアゾ成分として、６−アミノ−１−ヒドロキシナフ
タレン−８，５−ジスルホン酸を用いて、他は同様のア
ミン成分を用いることにより、遊離酸の形で下記構造の
モノアゾ化合物を得た。Example 2 In the same manner as in Example 1, 6-amino-1-hydroxynaphthalene-8,5-disulfonic acid was used as the azo component to perform the first condensation with cyanuric chloride, and the other same amine components were used. By using this, a monoazo compound having the following structure was obtained in the form of a free acid.
実施例３
下記アゾ成分Ａとジアゾ成分Ｂ１第２縮合ア電ン成分Ｃ
１第８縮合アミン成分りからなるモノアゾ化合物を実施
例１と同様の方法で合成した。Example 3 The following azo component A and diazo component B1 second condensed adenone component C
A monoazo compound consisting of the 1st and 8th condensed amine components was synthesized in the same manner as in Example 1.
これらの化合物は、アゾ成分（塩化シアヌルと第１縮合
を行なうアゾ成分）：Ａ欄、ジアゾ成分：Ｂ欄、第２縮
合アミン成分：Ｃ欄、第８縮合アミン成分＝Ｄ欄、並び
に合成されたモノアゾ化合物のセルロースｌａ維上での
色調：Ｅ欄により特徴づけられる。These compounds include the azo component (the azo component that performs the first condensation with cyanuric chloride): Column A, the diazo component: Column B, the second condensed amine component: Column C, the eighth condensed amine component = Column D, and the synthesized Color tone of the monoazo compound on cellulose LA fiber: Characterized by column E.
実施例４
実施例１〜８で得られた各々の化合物０．８部を２００
部の水に溶解し、芒硝１０部を加え、木綿１０部を加え
て６０゛Ｃに昇温する。Example 4 0.8 part of each compound obtained in Examples 1 to 8 was added to 200
of water, add 10 parts of Glauber's salt, add 10 parts of cotton, and raise the temperature to 60°C.
ついで、２０分経過後、炭酸ソーダ４部を加える。Then, after 20 minutes, 4 parts of carbonated soda are added.
その温度で１時間染色する。染色終了後、水洗、ソーピ
ングを行なって諸堅牢度のすぐれた緋色の染色物を得た
。Dye for 1 hour at that temperature. After dyeing, washing and soaping were performed to obtain a scarlet dyed product with excellent fastness.
実施例６
実施例１〜８で得られた各々の化合物１５部を尿素６０
部と共に熱水２００部中に溶解する。溶液に撹拌下アル
ギン酸ナトリウム４０部及び水９６０部から成る湖４０
０部及び重炭酸ナトリウム２０部を加える。次いで混合
物を水と湖で１０００部に調整する。この捺染ペースト
を用いて木綿織物を捺染する。Example 6 15 parts of each of the compounds obtained in Examples 1 to 8 was added to 60 parts of urea.
1 part in 200 parts of hot water. Add 40 parts of sodium alginate and 960 parts of water to the solution with stirring.
Add 0 parts and 20 parts of sodium bicarbonate. The mixture is then adjusted to 1000 parts with water and lake. This printing paste is used to print cotton fabrics.
乾燥後、６会同１００〜１０８℃でスチーミングし、冷
水で次いで熱水で洗浄し、煮沸ソーピングし再び洗浄し
乾燻する。このようにして極めて良好な諸堅牢度を有す
る濃度の高い緋色捺染物を得た。After drying, it is steamed at 100-108°C six times, washed with cold water, then hot water, boiled and soaped, washed again and dry-smoked. In this way a dense scarlet print with very good fastnesses was obtained.
Claims (7)
原子又は置換されていてもよい低級アルキル基を示しＢ
＿１、Ｂ＿２は互いに独立にメチル基、メトキシ基、エ
チル基、エトキシ基、塩素原子、臭素原子、スルホン酸
又はカルボン酸基によって置換されてもよいフェニレン
基、またはスルホン酸基で置換されてもよいナフチレン
基を示す。Ｙ＿１及びＹ＿２は互いに独立に−ＣＨ＝Ｃ
Ｈ＿２又は、−ＣＨ＿２ＣＨ＿２Ｚを示し、ここにＺは
アルカリの作用で脱離する基を示す。ｍ及びｎは０又は
１を表わす。〕 で示される水溶性モノアゾ化合物。(1) In the form of a free acid, the following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R_1, R_2 and R_3 are independently hydrogen atoms or optionally substituted lower B indicates an alkyl group
_1 and B_2 may be independently substituted with a methyl group, a methoxy group, an ethyl group, an ethoxy group, a chlorine atom, a bromine atom, a phenylene group that may be substituted with a sulfonic acid or a carboxylic acid group, or a sulfonic acid group Indicates a naphthylene group. Y_1 and Y_2 independently of each other -CH=C
It represents H_2 or -CH_2CH_2Z, where Z represents a group that is eliminated by the action of an alkali. m and n represent 0 or 1. ] A water-soluble monoazo compound represented by
子、メチル基又はエチル基である特許請求の範囲第１項
に記載のモノアゾ化合物。(2) The monoazo compound according to claim 1, wherein R_1, R_2 and R_3 are each independently a hydrogen atom, a methyl group or an ethyl group.
メトキシ基で置換されてもよいフェニレン基である特許
請求の範囲第１項又は第２項に記載のモノアゾ化合物。(3) The monoazo compound according to claim 1 or 2, wherein B_1 and B_2 are each independently a phenylene group which may be substituted with a methyl group or a methoxy group.
ル基である特許請求の範囲第１項〜第３項のいずれかに
記載のモノアゾ化合物。(4) The monoazo compound according to any one of claims 1 to 3, wherein Y_1 and Y_2 are both β-sulfatoethyl groups.
す。〕 で示される特許請求の範囲第１項に記載のモノアゾ化合
物。(5) In the form of free acid, the following general formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, R_4 represents a hydrogen atom, a methyl group, or an ethyl group. ] The monoazo compound according to claim 1, which is represented by:
す。〕 で示される特許請求の範囲第１項に記載のモノアゾ化合
物。(6) In the form of free acid, the following general formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) [In the formula, R_5 represents a hydrogen atom, a methyl group, or an ethyl group. ] The monoazo compound according to claim 1, which is represented by:
原子又は置換されてもよい低級アルキル基を示しＢ＿１
、Ｂ＿２は互いに独立にメチル基、メトキシ基、エチル
基、エトキシ基、塩素原子、塩素原子、臭素原子、スル
ホン酸又はカルボン酸基によって置換されてもよいフェ
ニレン基、またはスルホン酸基で置換されてもよいナフ
チレン基を示す。Ｙ＿１及びＹ＿２は互いに独立に−Ｃ
Ｈ＝ＣＨ＿２又は−ＣＨ＿２ＣＨ＿２Ｚを示し、ここに
Ｚはアルカリの作用で脱離する基を示す。ｍ及びｎは０
又は１を表わす。〕 で示される水溶性モノアゾ化合物を用いることを特徴と
するヒドロキシ基及び／又はカルボンアミド基含有材料
を染色又は捺染する方法。(7) In the form of flowing acid, the following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R_1, R_2 and R_3 are independently hydrogen atoms or optionally substituted lower alkyl Indicates the group B_1
, B_2 are independently substituted with a methyl group, a methoxy group, an ethyl group, an ethoxy group, a chlorine atom, a chlorine atom, a bromine atom, a phenylene group which may be substituted with a sulfonic acid or carboxylic acid group, or a sulfonic acid group. This indicates a good naphthylene group. Y_1 and Y_2 are independently -C
H=CH_2 or -CH_2CH_2Z, where Z represents a group that is eliminated by the action of an alkali. m and n are 0
Or represents 1. ] A method for dyeing or printing a material containing a hydroxyl group and/or a carbonamide group, characterized by using a water-soluble monoazo compound shown in the following.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61248201A JPH0753832B2 (en) | 1986-10-17 | 1986-10-17 | Water-soluble monoazo compound and method for dyeing or printing fiber material using the same |
| US07/106,798 US4904766A (en) | 1986-10-17 | 1987-10-13 | Monoazo compound having two vinylsulfone type fiber reactive groups through triazinyl bridging group |
| KR1019870011483A KR960000173B1 (en) | 1986-10-17 | 1987-10-16 | Scarlet color monoazo compound, the process for producing the same and the process for dyeing or printing fiber material using the same |
| EP87115146A EP0264137B1 (en) | 1986-10-17 | 1987-10-16 | Scarlet monoazo compound having two vinylsulfone type fiber reactive groups |
| DE8787115146T DE3770749D1 (en) | 1986-10-17 | 1987-10-16 | TWO FIBER REACTIVE GROUPS OF THE SCARLACH MONOAZO COMPOUND CONTAINING VINYL SULPHON SERIES. |
| ES87115146T ES2022259B3 (en) | 1986-10-17 | 1987-10-16 | SINGLE COLOR SINGLE-COLOR COMPOUNDS WITH 2 REACTIVE GROUPS OF VINYL SULPHONE TYPE FIBER. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61248201A JPH0753832B2 (en) | 1986-10-17 | 1986-10-17 | Water-soluble monoazo compound and method for dyeing or printing fiber material using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63101458A true JPS63101458A (en) | 1988-05-06 |
| JPH0753832B2 JPH0753832B2 (en) | 1995-06-07 |
Family
ID=17174699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61248201A Expired - Fee Related JPH0753832B2 (en) | 1986-10-17 | 1986-10-17 | Water-soluble monoazo compound and method for dyeing or printing fiber material using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0753832B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001335719A (en) * | 2000-05-26 | 2001-12-04 | Sumitomo Chem Co Ltd | Reactive dye mixture and its application |
| JP2001348504A (en) * | 2000-06-06 | 2001-12-18 | Sumitomo Chem Co Ltd | Reactive dye composition and application of the same |
| JP2001348506A (en) * | 2000-06-09 | 2001-12-18 | Sumitomo Chem Co Ltd | Reactive dye composition and application of the same to textile material |
| JP2002069864A (en) * | 2000-08-31 | 2002-03-08 | Sumitomo Chem Co Ltd | Method for dyeing mixed cellulosic and polyamide fiber |
| JP2002179944A (en) * | 2000-12-12 | 2002-06-26 | Sumitomo Chem Co Ltd | Reactive dye composition and its application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5871957A (en) * | 1981-10-02 | 1983-04-28 | チバ・ガイギ−・アクチエンゲゼルシヤフト | Reactive dye and manufacture |
-
1986
- 1986-10-17 JP JP61248201A patent/JPH0753832B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5871957A (en) * | 1981-10-02 | 1983-04-28 | チバ・ガイギ−・アクチエンゲゼルシヤフト | Reactive dye and manufacture |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001335719A (en) * | 2000-05-26 | 2001-12-04 | Sumitomo Chem Co Ltd | Reactive dye mixture and its application |
| JP4538897B2 (en) * | 2000-05-26 | 2010-09-08 | 住友化学株式会社 | Reactive dye mixture and its application |
| JP2001348504A (en) * | 2000-06-06 | 2001-12-18 | Sumitomo Chem Co Ltd | Reactive dye composition and application of the same |
| JP4538901B2 (en) * | 2000-06-06 | 2010-09-08 | 住友化学株式会社 | Reactive dye composition and application thereof |
| JP2001348506A (en) * | 2000-06-09 | 2001-12-18 | Sumitomo Chem Co Ltd | Reactive dye composition and application of the same to textile material |
| JP2002069864A (en) * | 2000-08-31 | 2002-03-08 | Sumitomo Chem Co Ltd | Method for dyeing mixed cellulosic and polyamide fiber |
| JP2002179944A (en) * | 2000-12-12 | 2002-06-26 | Sumitomo Chem Co Ltd | Reactive dye composition and its application |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0753832B2 (en) | 1995-06-07 |
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