JPH0365392B2 - - Google Patents
Info
- Publication number
- JPH0365392B2 JPH0365392B2 JP57048746A JP4874682A JPH0365392B2 JP H0365392 B2 JPH0365392 B2 JP H0365392B2 JP 57048746 A JP57048746 A JP 57048746A JP 4874682 A JP4874682 A JP 4874682A JP H0365392 B2 JPH0365392 B2 JP H0365392B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- sulfonic acid
- dye
- formula
- dye composition
- 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
- 239000000975 dye Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- 239000000985 reactive dye Substances 0.000 claims description 6
- 229920003043 Cellulose fiber Polymers 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 27
- 238000004043 dyeing Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 aminoazobenzene compound Chemical class 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 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 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JCRMBLKUFLUWPU-UHFFFAOYSA-N 2-ethylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CC)=CC=C21 JCRMBLKUFLUWPU-UHFFFAOYSA-N 0.000 description 2
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 150000004699 copper complex Chemical class 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
- 238000001035 drying Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-M sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- BMRVLXHIZWDOOK-UHFFFAOYSA-N 2-butylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC=C21 BMRVLXHIZWDOOK-UHFFFAOYSA-N 0.000 description 1
- FWMKPJYJDJSEHR-UHFFFAOYSA-N 2-propylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCC)=CC=C21 FWMKPJYJDJSEHR-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000004698 Polyethylene 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
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- KUIXZSYWBHSYCN-UHFFFAOYSA-L remazol brilliant blue r Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC(S(=O)(=O)CCOS([O-])(=O)=O)=C1 KUIXZSYWBHSYCN-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229940001496 tribasic sodium phosphate Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明は、水又は水性アルカリ液に対して、極
めて高い溶解度を有する染料組成物に関する。
遊離酸の形で下記一般式（）
〔式中、Ｑは−SO2CH＝CH2、又は−
SO2CH2CH2R（Ｒはアルカリで除去し得る基を意
味する）を示し、R1及びR2はそれぞれ独立に水
素、メチル基又はメトキシ基、Ｘはメチル基、メ
トキシ基、Ｙは水素基、アミノ基、又はアシルア
ミノ基を示す。ｍは０又は１、ｎは１〜３の整数
を示す。ナフタレン環に結合する基−Ｎ＝Ｎ−及
び基−Ｏ−は隣接するものとし、且つ一方がα位
で他方がβ位であるものとする。ベンゼン環に結
合する基−Ｏ−は、ｍ＝０のとき環Ａの−Ｎ＝Ｎ
−に対してオルト位に、又ｍ＝１のとき環βの基
Ｘに対してパラ位にあるものとする〕
で表わされる染料は、セルロース繊維を紫色ない
し青色に染色するに多用されている有用な染料で
ある。
しかし、上記一般式（）で示される染料は、
天然及び再生セルロース繊維を染色する為に有効
な一浴一パジング差上げ法、一浴一パジング−乾
燥法及び一浴一パジングスチーミング法等の染色
法に適用する場合、水性アルカリ液例えば苛性ソ
ーダ、炭酸ナトリウム又は第三リン酸ナトリウム
及び電解質を含む水性アルカリ液に対する溶解性
が不充分な為に均一で斑点のない濃色の染色物を
得ることは困難である。
このような水性アルカリ液に対する溶解性を改
良する方法として、特開昭50−132271号公報に
は、C.I.リアクテイブブルー19（ナトリウム塩）、
アントラキノン−２−スルホン酸（ナトリウム
塩）、ナフタリン−スルホン酸とホルムアルデヒ
ドとの縮合生成物（ナトリウム塩）、縮合リン酸
塩（ナトリウム塩）及び飛散防止剤からなる染料
組成物が提案されている。しかし上記一般式
（）で示される染料についてこの方法を適用し
ても、尚十分な溶解性を得ることは困難である。
本発明者らは、このような問題を解決すべく
種々検討の結果、上記一般式（）で示される染
料、及びアルキルナフタレンスルホン酸とホルム
アルデヒドとの縮合物をを含有する組成物が水性
アルカリ液に対する溶解性が十分であり、上述し
た天然及び再生セルロース繊維を染色する為に有
効な染色法に適用できることを見出し本発明を完
成するに至つた。
即ち、本発明は上記一般式（）で示される染
料及びアルキルナフタレンスルホンとホルムアル
デヒドとの縮合物を重量比で80〜20：20〜80含有
するセルロース繊維用反応染料組成物を提供する
ものである。
本発明で用いる一般式（）で示される染料は
例えば、下記式（）
（式中、R1，R2，ｍ，Ｘ，及びＱは前記の通
り、R3は水素又はメチル基を示す）
で示されるアニリン又はアミノアゾベンゼン化合
物を通常の方法でジアゾ化し、これと下式（）
（式中、Ｙ及びｎは前記の通り）
で示されるナフトールスルホン酸を通常の方法で
カツプリングさせた後、銅塩を用いて通常の方法
により錯銅化することにより製造できる。
また一般式（）
（式中、R1，R2，R3，Ｘ，及びｍは前記の通
り）
で示されるアニリン又はアミノアゾベンゼン化合
物を通常の方法でジアゾ化し、これを一般式
（）で示されるナフトールスルホン酸に通常の
方法でカツプリングさせた後、銅塩を用いて通常
の方法により錯銅化した後、さらに硫酸等でエス
テル化することによつても製造できる。
式（）で示されるアニリン化合物及びアミノ
アゾベンゼン化合物としては夫々下記の化合物が
例示される。
The present invention relates to dye compositions having extremely high solubility in water or aqueous alkaline liquids. The general formula below in the free acid form () [In the formula, Q is −SO 2 CH=CH 2 or −
SO 2 CH 2 CH 2 R (R means a group that can be removed with an alkali), R 1 and R 2 are each independently hydrogen, methyl group or methoxy group, X is methyl group, methoxy group, Y is Indicates a hydrogen group, an amino group, or an acylamino group. m represents 0 or 1, and n represents an integer of 1 to 3. The group -N=N- and the group -O- bonded to the naphthalene ring are assumed to be adjacent, and one is assumed to be in the α position and the other in the β position. The group -O- bonded to the benzene ring is -N=N of ring A when m=0.
-, and when m = 1, it is assumed to be in the para position to the group It is a useful dye. However, the dye represented by the above general formula () is
When applied to dyeing methods such as the one-bath-one-padding-drying method, the one-bath-one-padding-drying method, and the one-bath, one-padding steaming method, which are effective for dyeing natural and regenerated cellulose fibers, an aqueous alkaline solution such as caustic soda is used. Due to the insufficient solubility in aqueous alkaline solutions containing sodium carbonate or tribasic sodium phosphate and electrolytes, it is difficult to obtain uniform, spot-free, dark dyeings. As a method of improving the solubility in such aqueous alkaline solutions, JP-A-50-132271 discloses CI Reactive Blue 19 (sodium salt),
Dye compositions comprising anthraquinone-2-sulfonic acid (sodium salt), a condensation product of naphthalene-sulfonic acid and formaldehyde (sodium salt), a condensed phosphate (sodium salt), and an anti-scattering agent have been proposed. However, even if this method is applied to the dye represented by the above general formula (), it is still difficult to obtain sufficient solubility. As a result of various studies to solve these problems, the present inventors have discovered that a composition containing a dye represented by the above general formula () and a condensate of alkylnaphthalene sulfonic acid and formaldehyde can be used in an aqueous alkaline solution. The inventors have found that the dye has sufficient solubility in the cellulose fibers and can be applied to the effective dyeing method for dyeing the above-mentioned natural and regenerated cellulose fibers, leading to the completion of the present invention. That is, the present invention provides a reactive dye composition for cellulose fibers containing a dye represented by the above general formula () and a condensate of alkylnaphthalene sulfone and formaldehyde in a weight ratio of 80 to 20:20 to 80. . The dye represented by the general formula () used in the present invention is, for example, the following formula () ( In the formula, R 1 , R 2 , m, formula() (In the formula, Y and n are as described above) It can be produced by coupling naphtholsulfonic acid represented by the following in a conventional manner, and then forming a copper complex in a conventional manner using a copper salt. Also general formula () (In the formula, R 1 , R 2 , R 3 , X, and m are as described above) Diazotize the aniline or aminoazobenzene compound represented by It can also be produced by coupling with a conventional method, forming a copper complex using a copper salt in a conventional method, and then esterifying with sulfuric acid or the like. The following compounds are exemplified as the aniline compound and aminoazobenzene compound represented by formula ().
【式】【formula】
（式中、Ｑは前記の通り）
また式（）で示されるナフトールスルホン酸
としは夫々下記の化合物が例示される。
本発明におけるアルキルナフタレンスルホン酸
としては例えばメチルナフタレンスルホン酸、エ
チルナフタレンスルホン酸、プロピルナフタレン
スルホン酸、ブチルナフタレンスルホン酸などが
あげられこれらの内から選ばれた一種または二種
以上のものが用いられる。
これらのアルキルナフタレンスルホン酸のスル
ホン化度（アルキルナフタレン１モルに対しスル
ホン酸１モルが付いたものをスルホン化度100％
とする）は好ましくは平均50〜150％更に好まし
くは80〜120％である。
これらのアルキルナフタレンスルホン酸とホル
ムアルデヒドとの縮合物はアルカリ金属塩として
用いることができ、またその平均縮合度は好まし
くは1.1〜3.0、更に好ましくは1.5〜2.5である。
本発明の染料組成物は上記一般式（）で示さ
れる染料及びアルキルナフタレンスルホン酸とホ
ルムアルデヒドとの縮合物を20〜80：80〜20、好
ましくは50〜70：50〜30（重量比）の割合で混合
して得られる。
さらに本発明の染料組成物には、尿素やアント
ラキノン−２−スルホン酸などのヒドロトロープ
剤、デキストリンや庶糖など染料組成物の溶解に
全くまたはほとんど影響を与えない物質を含有す
ることができる。また少量で染料組成物の溶解性
に悪影響が無い範囲内で塩化ナトリウムや硫酸ナ
トリウム等の混入や、鉱油エマルジヨン等、飛散
防止剤の添加はさしつかえない。
以下実施例によつて、本発明を更に詳しく説明
する。文中部は重量部を表わす。
実施例 １
下記構造を有する反応染料
の純度78％のコンクケーキ65部、スルホン化度
100％、平均縮合度2.5のエチルナフタレンスルホ
ン酸とホルムアルデヒドとの縮合物（ナトリウム
塩）34部と鉱油エマルジヨン１部を加え充分混合
する。
(イ) 得られた染料組成物100ｇを、熱水で溶解し、
25℃に冷却する。これに32.5％の苛性ソーダ水
溶液および50゜ボーメの水ガラス150ｇを添加し
さらに水を加えて、全量を25℃で１にした直
後に、この液をパジング液として用いて本綿織
物を巻上げ、ポリエチレンフイルムで密閉して
20℃の室内で20時間放置後染色物を冷水、次に
熱湯で洗浄し、沸騰している洗剤液中でソーピ
ングし、さらに冷水で洗浄後、乾燥して仕上げ
る。これによりきわめて濃い赤色の斑のない染
色物が得られた。
(ロ) 上記(イ)項のパジング液を25℃にて60分間放置
後も染料の析出は全く認められず、また(イ)項と
同様に木綿織物のパジング染色を行なうと、均
一で斑のないきわめて濃い赤色染色物が得られ
た。
比較例 １
純度78％の前記反応染料65部ナフタレンスルホ
ン酸とホルムアルデヒドとの縮合物（ナトリウム
塩）34部と鉱油エマルジヨン１部とを加え充分混
合する。
(イ) 得られた染料組成物120ｇを用いて実施例１
の(イ)項に従つてパジング液を調整する。調整直
後は染料の析出も認められず、木綿織物をパジ
ング染色して斑のない染色物が得られた。
(ロ) 上記(イ)項の液を25℃にて３分間放置すると、
多量の染料が析出し、この液を用いて木綿織物
を染色しても著しく斑のある実用上価値のない
染色物しか得られなかつた。
実施例 ２
下記構造を有する反応染料
の純度84％のコンクケーキ68部、スルホン化度
120％、平均縮合度1.8のメチルナフタレンスルホ
ン酸とホルムアルデヒドとの縮合物31部及びアン
トラキノン−２−スルホン酸ナトリウム７部と鉱
油エマルジヨン１部とを加え充分に混合する。
(イ) 得られた染料組成物70ｇを用いて実施例１の
(イ)項と同様にしてパジング液１を調整し、木
綿織物をパジング染色すると斑のない均ーな、
きわめて濃い赤色の染色物が得られた。
(ロ) 上記(イ)項のパジング液を25℃で60分間放置後
にも染料の析出は全く認められず、又この液を
用いて木綿織物をパジング染色したところ均一
で斑のないきわめて濃い赤色の染色物が得られ
た。
比較例 ２
特開昭50−132271号公報の実施例３に記載の方
法に従つて、純度84％の前記染料コンクケーキ68
部、アントラキノン−２−スルホン酸ナトリウム
７部、尿素４部、縮合リン酸塩４部、ナフタレン
スルホン酸とホルムアルデヒドとの縮合物（ナト
リウム塩）14部及び鉱油エマルジヨン３部を混合
する。
(イ) 得られた染料組成物70ｇを用いて実施例１の
(イ)項に従つてパジング液を調整したが10分間で
染液がゲル化した染色不可能となつた。 (In the formula, Q is as described above.) Examples of the naphtholsulfonic acid represented by the formula () include the following compounds. Examples of alkylnaphthalenesulfonic acids in the present invention include methylnaphthalenesulfonic acid, ethylnaphthalenesulfonic acid, propylnaphthalenesulfonic acid, butylnaphthalenesulfonic acid, and one or more selected from these are used. . The sulfonation degree of these alkylnaphthalene sulfonic acids (sulfonation degree of 1 mole of sulfonic acid per 1 mole of alkylnaphthalene is 100%)
) is preferably on average 50 to 150%, more preferably 80 to 120%. These condensates of alkylnaphthalene sulfonic acids and formaldehyde can be used as alkali metal salts, and the average degree of condensation is preferably 1.1 to 3.0, more preferably 1.5 to 2.5. The dye composition of the present invention contains the dye represented by the above general formula () and the condensate of alkylnaphthalene sulfonic acid and formaldehyde in a ratio of 20 to 80:80 to 20, preferably 50 to 70:50 to 30 (weight ratio). Obtained by mixing in proportions. Furthermore, the dye composition of the present invention may contain a hydrotrope such as urea or anthraquinone-2-sulfonic acid, or a substance that has no or little effect on the dissolution of the dye composition, such as dextrin or sucrose. In addition, it is permissible to mix in sodium chloride, sodium sulfate, etc. or add anti-scattering agents such as mineral oil emulsion within a small amount that does not adversely affect the solubility of the dye composition. The present invention will be explained in more detail with reference to Examples below. The middle part of the sentence indicates parts by weight. Example 1 Reactive dye having the following structure 65 parts of conch cake with a purity of 78%, degree of sulfonation
Add 34 parts of a condensate (sodium salt) of 100% ethylnaphthalene sulfonic acid and formaldehyde with an average degree of condensation of 2.5 and 1 part of mineral oil emulsion and mix thoroughly. (a) Dissolve 100g of the obtained dye composition in hot water,
Cool to 25°C. Immediately after adding 32.5% caustic soda aqueous solution and 150 g of 50° Baumé water glass and adding water to bring the total volume to 1 at 25°C, this liquid was used as a padding liquid to wind up a real cotton fabric and polyethylene film was added. Seal it with
After being left in a room at 20°C for 20 hours, the dyed item is washed with cold water, then hot water, soaped in a boiling detergent solution, washed with cold water, and dried. This gave a very deep red spotless dyeing. (b) Even after leaving the padding solution in item (a) above at 25℃ for 60 minutes, no dye precipitation was observed, and when padding dyed cotton fabric in the same way as in item (a), it was uniform and uneven. A very deep red dyeing without any stains was obtained. Comparative Example 1 65 parts of the above reactive dye with a purity of 78% 34 parts of a condensate of naphthalene sulfonic acid and formaldehyde (sodium salt) and 1 part of mineral oil emulsion were added and thoroughly mixed. (a) Example 1 using 120 g of the obtained dye composition
Adjust the padding liquid according to (a). Immediately after the adjustment, no dye precipitation was observed, and the cotton fabric was pad-dyed and a dyed product with no spots was obtained. (b) If the solution in item (a) above is left at 25℃ for 3 minutes,
A large amount of dye was precipitated, and even when cotton fabrics were dyed with this solution, only dyed products were obtained that were extremely uneven and of no practical value. Example 2 Reactive dye having the following structure 68 parts of conch cake with a purity of 84%, degree of sulfonation
31 parts of a condensate of methylnaphthalenesulfonic acid and formaldehyde having an average degree of condensation of 120% and 1.8, 7 parts of sodium anthraquinone-2-sulfonate and 1 part of mineral oil emulsion are added and thoroughly mixed. (b) Using 70 g of the obtained dye composition, the procedure of Example 1 was carried out.
Adjust the padding liquid 1 in the same manner as in (a) and dye the cotton fabric with padding to obtain a uniform color with no spots.
A very deep red dyeing was obtained. (b) Even after leaving the padding solution in item (a) above at 25°C for 60 minutes, no dye precipitation was observed, and when padding cotton fabric was dyed with this solution, it was a uniform, very deep red color with no spots. A dyed product was obtained. Comparative Example 2 The dye conch cake 68 with a purity of 84% was prepared according to the method described in Example 3 of JP-A-50-132271.
1 part, 7 parts of sodium anthraquinone-2-sulfonate, 4 parts of urea, 4 parts of condensed phosphate, 14 parts of a condensate of naphthalene sulfonic acid and formaldehyde (sodium salt), and 3 parts of mineral oil emulsion. (b) Using 70 g of the obtained dye composition, the procedure of Example 1 was carried out.
The padding solution was prepared according to section (a), but within 10 minutes the dye solution turned into a gel and staining became impossible.
Claims (1)
SO2CH2CH2R（Ｒはアルカリで除去し得る基を意
味する）を示し、R1及びR2はそれぞれ独立に水
素、メチル基又はメトキシ基、Ｘはメチル基、メ
トキシ基、Ｙは水素、アミノ基、又はアシルアミ
ノ基を示す。ｍは０又は１、ｎは１〜３の整数を
示す。ナフタレン環に結合する基−Ｎ＝Ｎ−及び
基−Ｏ−は隣接するものとし、且つ一方がα位で
他方がβ位であるものとする。ベンゼン環に結合
する基−Ｏ−は、ｍ＝０のとき環Ａの−Ｎ＝Ｎ−
に対してオルト位に、又ｍ＝１のとき環Ｂの基Ｘ
に対してパラ位にあるものとする〕 で表わされる染料20−80重量％、およびアルキル
ナフタレンスルホン酸とホルムアルデヒドとの縮
合物が80−20重量％とからなることを特徴とする
セルロース繊維用反応染料組成物。 ２ アルキルナフタレンスルホン酸が低級アルキ
ルナフタレンスルホン酸である特許請求の範囲第
１項に記載の反応染料組成物。 ３ アルキルナフタレンスルホン酸がメチルナフ
タレンスルホン酸である特許請求の範囲第２項に
記載の反応染料組成物。[Claims] 1 The following general formula in the form of a free acid: [In the formula, Q is −SO 2 CH=CH 2 or −
SO 2 CH 2 CH 2 R (R means a group that can be removed with an alkali), R 1 and R 2 are each independently hydrogen, methyl group or methoxy group, X is methyl group, methoxy group, Y is Indicates hydrogen, an amino group, or an acylamino group. m represents 0 or 1, and n represents an integer of 1 to 3. The group -N=N- and the group -O- bonded to the naphthalene ring are assumed to be adjacent, and one is assumed to be in the α position and the other in the β position. The group -O- bonded to the benzene ring is -N=N- of ring A when m=0.
, and when m=1, the group X of ring B
A reaction for cellulose fiber characterized by comprising 20-80% by weight of a dye represented by: Dye composition. 2. The reactive dye composition according to claim 1, wherein the alkylnaphthalene sulfonic acid is lower alkylnaphthalene sulfonic acid. 3. The reactive dye composition according to claim 2, wherein the alkylnaphthalene sulfonic acid is methylnaphthalene sulfonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4874682A JPS58164652A (en) | 1982-03-25 | 1982-03-25 | Reactive dye composition for cellulose fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4874682A JPS58164652A (en) | 1982-03-25 | 1982-03-25 | Reactive dye composition for cellulose fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58164652A JPS58164652A (en) | 1983-09-29 |
| JPH0365392B2 true JPH0365392B2 (en) | 1991-10-11 |
Family
ID=12811843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4874682A Granted JPS58164652A (en) | 1982-03-25 | 1982-03-25 | Reactive dye composition for cellulose fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58164652A (en) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5152435A (en) * | 1974-09-05 | 1976-05-10 | Hoechst Ag | Senryo ganryooyobi kogakutekimeishokukazaio bifunsanoyobi anteikasurutamenobunsanzai |
| JPS53145842A (en) * | 1977-05-24 | 1978-12-19 | Sandoz Ag | Aqueous dyestuff formulation |
| JPS55107582A (en) * | 1979-02-13 | 1980-08-18 | Sumitomo Chemical Co | Reactive dyestuff composition for cellulosic fiber |
| JPS5673181A (en) * | 1979-11-13 | 1981-06-17 | Sumitomo Chemical Co | Reactive dyestuff composition for cellulose fiber |
| JPS56103250A (en) * | 1980-01-21 | 1981-08-18 | Sumitomo Chem Co Ltd | Reactive dye composition and dyeing using the same |
| JPS56140186A (en) * | 1980-03-31 | 1981-11-02 | Sumitomo Chemical Co | Reactive dyestuff liquid composition |
| JPS56143257A (en) * | 1980-04-11 | 1981-11-07 | Sumitomo Chem Co Ltd | Reactive dye composition and dyeing method employing the same |
| JPS56159374A (en) * | 1980-05-12 | 1981-12-08 | Sumitomo Chemical Co | Dyeing and printing method by reactive dyestuff |
-
1982
- 1982-03-25 JP JP4874682A patent/JPS58164652A/en active Granted
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5152435A (en) * | 1974-09-05 | 1976-05-10 | Hoechst Ag | Senryo ganryooyobi kogakutekimeishokukazaio bifunsanoyobi anteikasurutamenobunsanzai |
| JPS53145842A (en) * | 1977-05-24 | 1978-12-19 | Sandoz Ag | Aqueous dyestuff formulation |
| JPS55107582A (en) * | 1979-02-13 | 1980-08-18 | Sumitomo Chemical Co | Reactive dyestuff composition for cellulosic fiber |
| JPS5673181A (en) * | 1979-11-13 | 1981-06-17 | Sumitomo Chemical Co | Reactive dyestuff composition for cellulose fiber |
| JPS56103250A (en) * | 1980-01-21 | 1981-08-18 | Sumitomo Chem Co Ltd | Reactive dye composition and dyeing using the same |
| JPS56140186A (en) * | 1980-03-31 | 1981-11-02 | Sumitomo Chemical Co | Reactive dyestuff liquid composition |
| JPS56143257A (en) * | 1980-04-11 | 1981-11-07 | Sumitomo Chem Co Ltd | Reactive dye composition and dyeing method employing the same |
| JPS56159374A (en) * | 1980-05-12 | 1981-12-08 | Sumitomo Chemical Co | Dyeing and printing method by reactive dyestuff |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58164652A (en) | 1983-09-29 |
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