JPH0372106B2 - - Google Patents
Info
- Publication number
- JPH0372106B2 JPH0372106B2 JP57205625A JP20562582A JPH0372106B2 JP H0372106 B2 JPH0372106 B2 JP H0372106B2 JP 57205625 A JP57205625 A JP 57205625A JP 20562582 A JP20562582 A JP 20562582A JP H0372106 B2 JPH0372106 B2 JP H0372106B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- dye
- general formula
- 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.)
- Expired - Lifetime
Links
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 239000000985 reactive dye Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229920003043 Cellulose fiber Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 18
- 238000004043 dyeing Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005406 washing Methods 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
- VVBWXXHFHCZJJA-UHFFFAOYSA-N 2-(3-aminophenyl)sulfonylethanol;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC=CC(S(=O)(=O)CCO)=C1 VVBWXXHFHCZJJA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-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
- 229920000297 Rayon Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [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
- 239000003513 alkali Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- -1 vinylsulfonyl Chemical group 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明はセルロース繊維類用反応性染料に係る
ものである。詳しくは、本発明はセルロース系繊
維、特に天然または再生セルロース繊維を堅牢か
つ濃厚な黄色に染色するビニルスルホニル型反応
性染料に関するものである。
本発明のセルロース類繊維類用反応性染料は一
般式〔〕
（式中、R1は水素、メチル基またはエチル基
を表わし、R2およびR3は水素、メチル基、メト
キシ基またはスルホン酸基を表わし、Ｘは水素、
メチル基、アセチルアミノ基または塩素を表わ
し、Ｙは水素、メトキシ基またはエトキシ基を表
わし、Ｚはスルホン酸基を１ケまたは２ケ有する
C1〜C4低級アルキルアミノ基またはフエニルア
ミノ基を表わし、ｎは２または３を表わす。）
で示されるビニルスルホニル型反応性染料であ
る。
本発明の前示一般式〔〕で表わされる染料
は、例えば一般式〔〕
（式中、R1、Ｘ、Ｙおよびｎは前示一般式
〔〕における同一の意義を有する。）で示される
色素類と下記一般式〔〕
Ｚ−Ｈ ……〔〕
（式中、Ｚは前示一般式〔〕におけると同一
の意義を有する。）で表わされるアミン類を水系
媒質中30〜40℃で縮合させ下記一般式〔〕
（式中、R1、Ｘ、Ｙ、Ｚおよびｎは前示一般
式〔〕におけると同一の意義を有する。）とな
しこれに下記一般式〔〕
（式中、R2およびR3は前示一般式〔〕にお
けると同一の意義を有する。）で表わされる化合
物を水系媒質中90〜95℃で縮合させることにより
容易に製造される。
本発明の反応性染料により染色し得るセルロー
ス繊維類としては木綿、麻等の天然繊維、ビスコ
ースレーヨン等の再生繊維またはセルロース繊維
とポリエステル繊維、ポリアクリロニトリル繊維
等の合成繊維との混紡品などが挙げられる。
本発明の反応性染料を用いてセルロース繊維類
を染色するには、酸結合剤例えば重炭酸ソーダ、
炭酸ソーダ等の無機アルカリまたはトリエチルア
ミン等の有機塩基の存在下通常行われる方法で染
色することができる。例えば浸染法で染色する場
合には食塩又は芒硝等の無機塩および酸結合剤の
存在下40〜60℃の温度条件下で通常の方法により
染色することができる。
さらに捺染法で染色する場合にも通常用いられ
る方法例えばアルギン酸ソーダ、尿素、還元防止
剤、酸結合剤を用いて行う方法で染色する事がで
きる。またパツドバツチ法、パツドスチーム法な
どビニルスルホニル型水溶性反応性染料に用いら
れる各種の染色法が適用できる。なお、本願発明
の染料は非常に高い染着率を有しており染色後の
廃水処理の点においても有利である。一方堅牢度
面も非常に良好で近年問題となつている塩素堅牢
度は従来の同一色調染料に比べ驚異的に高いレベ
ルにあり、複合堅牢度として問題になる汗一日光
堅牢度も高く黄色系染料としては非常に高い実用
価値を有している。
以下、本発明を実施例によつて具体的に説明す
るが、本発明はその要旨を超えない限りこれらの
実施例に限定されるものではない。
実施例 １
構造式
で示される染料0.3ｇを水300mlに溶解し、芒硝20
ｇを加え溶解して調製した染浴に綿布15ｇを浸漬
し30分を要して50℃迄昇温した。次いで炭酸ソー
ダ4.5ｇを添加し50℃で１時間染色した後水洗、
ソーピング、水洗、乾燥を行ない、黄色の染色物
を得た。本染料の染着度は非常に高く得られた染
色物は極めて濃厚であり耐塩素堅牢度は４級
（JIS 0884に準処し有効塩素20ppm）と非常にす
ぐれ耐光堅牢度、汗一日光堅牢度も良好であつ
た。
なお、本実施例で使用した染料は
式
で示される化合物１モル割合と３−アミノベンゼ
ンスルホン酸１モル割合を水媒中30〜40℃で液性
を炭酸ナトリウムで中性に保ちつつ３時間撹拌し
式
の染料とした後３−（β−ヒドロキシエチル）ス
ルホニルアニリン硫酸エステル１モル割合と水媒
中90〜95℃で液性を酢酸ナトリウムでPH５〜６に
保ちつつ10時間撹拌した後塩化カリウムで塩析し
て得た。
実施例 ２
構造式
で示される染料を用いて下記の処法で綿布を捺染
した。
染料 2.0ｇ
尿素 10.0ｇ
アルギン酸ソーダ 3.0ｇ
３−ニトロベンゼンスルホン酸ソーダ 0.5ｇ
ヘキサメタリン酸ソーダ 0.5ｇ
重炭酸ソーダ 1.0ｇ
水 残部
100.0ｇ
すなわち、上記組成の捺染糊を綿布に印捺し80
℃で中間乾燥後100℃で蒸熱処理次いで水洗、ソ
ーピング、水洗、乾燥を行なつた。
その結果耐光堅牢度、湿潤堅牢度の良好な濃厚
赤味黄色の染色物を得た。また本染色物の塩素堅
牢度は４級（JIS 0884に準処し有効塩素20ppm）
と非常にすぐれていた。
なお、本実施例で使用した染料は
式
で示される染料１モル割合と４−アミノベンゼン
スルホン酸１モル割合を水媒中30〜40℃で液性を
炭酸ナトリウムで中性に保ちつつ３時間撹拌し式
の染料とした後３−（β−ヒドロキシエチル）ス
ルホニルアニリン硫酸エステル１モル割合と水媒
中90〜95℃で液性を酢酸ナトリウムでPH５〜６に
保ちつつ10時間撹拌した後塩化カリウムで塩析し
て得た。
実施例 ３
前記の実施例１に準じた方法で下記一般式
で表わされる染料を用いて綿布を染色した結果は
表−１の通りである。
The present invention relates to reactive dyes for cellulose fibers. More specifically, the present invention relates to vinylsulfonyl-type reactive dyes that dye cellulosic fibers, particularly natural or regenerated cellulose fibers, in a fast and intense yellow color. The reactive dye for cellulosic fibers of the present invention has the general formula [] (In the formula, R 1 represents hydrogen, methyl group or ethyl group, R 2 and R 3 represent hydrogen, methyl group, methoxy group or sulfonic acid group, X is hydrogen,
Represents a methyl group, acetylamino group or chlorine, Y represents hydrogen, methoxy group or ethoxy group, Z has one or two sulfonic acid groups
It represents a C1 to C4 lower alkylamino group or a phenylamino group, and n represents 2 or 3. ) It is a vinylsulfonyl-type reactive dye represented by: The dye represented by the general formula [] of the present invention may be, for example, the dye represented by the general formula [] (In the formula, R 1 , X, Y and n have the same meanings as in the above general formula []) and the following general formula [] Z-H ... [] (wherein, Z has the same meaning as in the general formula [] shown above) is condensed in an aqueous medium at 30 to 40°C to form the following general formula [] (In the formula, R 1 , X, Y, Z and n have the same meanings as in the above general formula []) and the following general formula [] (wherein R 2 and R 3 have the same meanings as in the general formula []) is easily produced by condensing the compound represented by the formula in an aqueous medium at 90 to 95°C. Examples of cellulose fibers that can be dyed with the reactive dye of the present invention include natural fibers such as cotton and hemp, regenerated fibers such as viscose rayon, and blends of cellulose fibers and synthetic fibers such as polyester fibers and polyacrylonitrile fibers. Can be mentioned. For dyeing cellulose fibers with the reactive dyes of the invention, an acid binder such as sodium bicarbonate,
Dyeing can be carried out by a conventional method in the presence of an inorganic alkali such as soda carbonate or an organic base such as triethylamine. For example, in the case of dyeing by dip dyeing, the dyeing can be carried out by a conventional method in the presence of an inorganic salt such as common salt or mirabilite salt and an acid binder at a temperature of 40 to 60°C. Furthermore, when dyeing by a textile printing method, dyeing can be carried out by a commonly used method, such as a method using sodium alginate, urea, a reduction inhibitor, or an acid binder. Also, various dyeing methods used for vinylsulfonyl type water-soluble reactive dyes, such as a pad batch method and a pad steam method, can be applied. The dye of the present invention has a very high dyeing rate and is also advantageous in terms of wastewater treatment after dyeing. On the other hand, the fastness is also very good, and the fastness to chlorine, which has become a problem in recent years, is at an amazingly high level compared to conventional dyes with the same color tone.The fastness to sweat and sunlight, which is a problem in terms of composite fastness, is also high, giving it a yellowish color. It has very high practical value as a dye. Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples unless the gist thereof is exceeded. Example 1 Structural formula Dissolve 0.3g of the dye shown in 300ml of water,
15 g of cotton cloth was immersed in the dye bath prepared by adding and dissolving 15 g of cotton cloth, and the temperature was raised to 50° C. over 30 minutes. Next, 4.5g of soda carbonate was added and dyed at 50℃ for 1 hour, then washed with water.
A yellow dyed product was obtained by soaping, washing with water, and drying. The degree of dyeing of this dye is very high.The dyed product obtained is extremely dense, and the chlorine fastness is grade 4 (available chlorine 20 ppm according to JIS 0884), which is excellent.Light fastness, sweat day light fastness. It was also good. The dye used in this example has the formula 1 mole of the compound represented by the formula and 1 mole of 3-aminobenzenesulfonic acid were stirred in an aqueous medium at 30 to 40°C for 3 hours while keeping the liquid neutral with sodium carbonate. After preparing the dye, it was stirred with 1 molar proportion of 3-(β-hydroxyethyl)sulfonylaniline sulfate in an aqueous medium at 90 to 95°C while maintaining the pH at 5 to 6 with sodium acetate for 10 hours, and then salted with potassium chloride. Obtained by analysis. Example 2 Structural formula Cotton cloth was printed using the dye shown in the following method. Dye 2.0g Urea 10.0g Sodium alginate 3.0g Sodium 3-nitrobenzenesulfonate 0.5g Sodium hexametaphosphate 0.5g Sodium bicarbonate 1.0g Remaining water 100.0g That is, printing paste with the above composition was printed on cotton cloth.
After intermediate drying at 100°C, it was subjected to steam treatment at 100°C, followed by washing with water, soaping, washing with water, and drying. As a result, a rich reddish-yellow dyed product with good light fastness and wet fastness was obtained. In addition, the chlorine fastness of this dye is grade 4 (available chlorine 20ppm according to JIS 0884).
It was very good. The dye used in this example has the formula 1 mole of the dye shown by and 1 mole of 4-aminobenzenesulfonic acid are stirred in an aqueous medium at 30 to 40℃ for 3 hours while keeping the liquid neutral with sodium carbonate. After preparing the dye, it was stirred with 1 molar proportion of 3-(β-hydroxyethyl)sulfonylaniline sulfate in an aqueous medium at 90 to 95°C while maintaining the pH at 5 to 6 with sodium acetate for 10 hours, and then salted with potassium chloride. Obtained by analysis. Example 3 The following general formula was prepared in a manner similar to Example 1 above. The results of dyeing cotton cloth using the dye represented by are shown in Table 1.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
Claims (1)
を表わし、R2およびR3は水素、メチル基、メト
キシ基またはスルホン酸基を表わし、Ｘは水素、
メチル基、アセチルアミノ基または塩素を表わ
し、Ｙは水素、メトキシ基またはエトキシ基を表
わし、Ｚはスルホン酸基を１ケまたは２ケ有する
C1〜C4低級アルキルアミノ基またはフエニルア
ミノ基を表わし、ｎは２または３を表わす。）で
示されるセルロース繊維類用反応性染料。[Claims] 1. General formula (In the formula, R 1 represents hydrogen, methyl group or ethyl group, R 2 and R 3 represent hydrogen, methyl group, methoxy group or sulfonic acid group, X is hydrogen,
Represents a methyl group, acetylamino group or chlorine, Y represents hydrogen, methoxy group or ethoxy group, Z has one or two sulfonic acid groups
It represents a C1 to C4 lower alkylamino group or a phenylamino group, and n represents 2 or 3. ) Reactive dye for cellulose fibers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57205625A JPS5996174A (en) | 1982-11-24 | 1982-11-24 | Reactive dye for cellulose fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57205625A JPS5996174A (en) | 1982-11-24 | 1982-11-24 | Reactive dye for cellulose fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5996174A JPS5996174A (en) | 1984-06-02 |
| JPH0372106B2 true JPH0372106B2 (en) | 1991-11-15 |
Family
ID=16509980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57205625A Granted JPS5996174A (en) | 1982-11-24 | 1982-11-24 | Reactive dye for cellulose fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5996174A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61263A (en) * | 1984-06-12 | 1986-01-06 | Sumitomo Chem Co Ltd | Monoazo compound and dyeing or printing by using the same |
| US4873321A (en) * | 1986-10-17 | 1989-10-10 | Sumitomo Chemical Company, Limited | Monazo compounds having a triozinyl bridging group and two vinylsulfone type fiber reactive groups |
| JPH0751678B2 (en) * | 1987-05-14 | 1995-06-05 | 三菱化学株式会社 | Water-soluble monoazo dye |
| DE3850077T2 (en) * | 1987-06-30 | 1995-01-19 | Mitsubishi Chem Ind | WATER-SOLUBLE REACTIVE DYE MIXTURE AND METHOD FOR DYING CELLULOSE FIBERS. |
| GB9212472D0 (en) * | 1992-06-12 | 1992-07-22 | Ici Plc | Chemical compounds |
| WO2011086966A1 (en) * | 2010-01-15 | 2011-07-21 | 日本化薬株式会社 | Water-soluble azo compound or salts thereo, ink composition and colored body |
-
1982
- 1982-11-24 JP JP57205625A patent/JPS5996174A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5996174A (en) | 1984-06-02 |
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