JPH0368071B2 - - Google Patents
Info
- Publication number
- JPH0368071B2 JPH0368071B2 JP57113457A JP11345782A JPH0368071B2 JP H0368071 B2 JPH0368071 B2 JP H0368071B2 JP 57113457 A JP57113457 A JP 57113457A JP 11345782 A JP11345782 A JP 11345782A JP H0368071 B2 JPH0368071 B2 JP H0368071B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- amino
- parts
- compound
- 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
- -1 propionylamino group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 12
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
- 238000004043 dyeing Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 229920006306 polyurethane fiber Polymers 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 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
- 239000004753 textile Substances 0.000 description 2
- 229940001496 tribasic sodium phosphate Drugs 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 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
- YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 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
- 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 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
- 238000011437 continuous method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010016 exhaust dyeing Methods 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
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004513 sizing Methods 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
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Description
本発明は、セルローズ繊維、天然または合成ポ
リアミド繊維、ポリウレタン繊維あるいは皮革等
の染色および捺染に有用な繊維反応性化合物に関
する。
更に詳しくは、本発明は遊離酸の形で下記一般
式（）
（式中、Ｄはメチル基、エチル基、メトキシ
基、エトキシ基、アセチルアミノ基、プロピオニ
ルアミノ基、サクシニルアミノ基、マレイニルア
ミノ基、スルホン酸基及びカルボキシル基の群か
らなる１、２又は３個の置換基により置換されて
いるフエニル基、或いはスルホン酸基１、２又は
３個で置換されているナフチル基を表わす。Ｘは
β−スルフアートエチル、β−チオスルフアート
エチル、β−ホスフアートエチル、β−クロルエ
チル又はビニルを表わし、Ｙは水素原子、塩素原
子又はスルホン酸基を表わし、Ｚは水素原子又は
メチル基を表わす。Ｒは炭素数４までの低級アル
キル基を表わす。）
で示される二官能型繊維反応性化合物に関する。
本発明化合物は遊離酸の形で又はその塩の形で
存在し、特にアルカリ金属塩及びアルカリ土類金
属塩、特にナトリウム塩、カリウム塩、カルシウ
ム塩が好ましい。
本発明化合物が繊維材料の染色および捺染に使
用されるときは、アルカリ金属塩が特に好まし
い。
本発明化合物は、例えば次の様にして製造する
ことができる。
下記一般式（）
Ｄ−NH2 （）
（式中Ｄは前記の意味を有する。）で示される
芳香族アミンを水性媒体中、通常の方法でジアゾ
化し、７−アミノ−４−ヒドロキシナフタレン−
２−スルホン酸のＮ−アシル化物又はＮ−メチル
−Ｎ−アシル化物と、０℃ないし30℃の温度、PH
５ないしPH９に調整しながらカツプリング反応を
行なつた後、酸又はアルカリの存在下50℃ないし
100℃の温度でアシル基を加水分解して、式（）
で示されるモノアゾ化合物を得る。
（式中、Ｄ、Ｚは前記の意味を有する。）
ついで、式（）の化合物を水性媒体中温度０
℃ないし30℃で、PHないしPH７に調整しながら、
塩化シアヌルと一次的に縮合させてジクロルトリ
アジニル化合物を得、続いて一般式（）
（式中、Ｒ、Ｘ、Ｙは前記の意味を有する。）
で示される化合物を、温度30℃ないし60℃で、PH
４ないしPH７に調整しながら二次的に縮合させ
て、一般式（）の化合物を得ることができる。
あるいは、一般式（）の化合物を、水性媒体
中温度０℃ないし30℃で、PH３ないしPH７に調整
しながら、塩化シアヌルと一次的に縮合させ、つ
いで温度20℃ないし50℃で、PH４ないしPH７に調
整しながら、一般式（）のモノアゾ化合物を二
次的に縮合させることによつても一般式（）の
化合物を得ることができる。
あるいは、７−アミノ−４−ヒドロキシナフタ
レン−２−スルホン酸又は７−Ｎ−メチルアミノ
−４−ヒドロキシナフタレン−２−スルホン酸と
式（）の化合物を任意の順序で、水性媒体中一
次的には温度０℃ないし30℃でPH３ないしPH７に
調整しながら、二次的には温度20℃ないし60℃で
PH４ないしPH７に調整しながら、塩化シアヌルと
縮合させて一般式（）
（式中、Ｒ、Ｘ、Ｙ、Ｚは前記の意味を有す
る。）
で示されるモノクロルトリアジニル化合物を得、
続いて一般式（）で示される芳香族アミンのジ
アゾニウム塩と温度０℃ないし30℃で、PH５ない
しPH９に調整しながらカツプリングさせることに
よつても一般式（）の化合物を得ることができ
る。
一般式（）で示される化合物は、下記一般式
（）
（式中、Ｘ、Ｙは前記の意味を有する。）
で示される化合物を相当する炭素数を有する塩化
アルキル、臭化アルキル、ヨウ化アルキル、硫酸
ジアルキル、ｐ−トルエンスルホン酸アルキル等
のアルキル化剤により、温度20℃ないし80℃でPH
４ないしPH７に調整しながら、アルキル化するこ
とにより得ることができる。
一般式（）で示される芳香族アミンとして
は、たとえば、
２−アミノベンゼンスルホン酸
２−アミノ−５−メチルベンゼンスルホン酸
２−アミノ−５−メトキシベンゼンスルホン酸
２−アミノ−５−エトキシベンゼンスルホン酸
２−アミノ−５−アセチルアミノベンゼンスル
ホン酸
２−アミノ−５−プロピオニルアミノベンゼン
スルホン酸
２−アミノ−５−サクシニルアミノベンゼンス
ルホン酸
２−アミノ−５−マレイニルアミノベンゼンス
ルホン酸
２−アミノ−４−メトキシベンゼンスルホン酸
２−アミノ−４−エトキシベンゼンスルホン酸
２−アミノ−４−アセチルアミノベンゼンスル
ホン酸
２−アミノ−４−ピロピオニルアミノベンゼン
スルホン酸
２−アミノ−４−サクシニルアミノベンゼンス
ルホン酸
２−アミノ−４−マレイニルアミノベンゼンス
ルホン酸
３−アミノ−４−メチルベンゼンスルホン酸
３−アミノ−４−メトキシベンゼンスルホン酸
３−アミノ−４−エトキシベンゼンスルホン酸
４−アミノ−３−メチルベンゼンスルホン酸
４−アミノ−３−メトキシベンゼンスルホン酸
４−アミノ−３−エトキシベンゼンスルホン酸
２−アミノベンゼン−１，４−ジスルホン酸
２−アミノベンゼン−１，５−ジスルホン酸
２−アミノ安息香酸
２−アミノ−４−メトキシ安息香酸
２−アミノ−５−メトキシ安息香酸
２−アミノ−４−アセチルアミノ安息香酸
２−アミノ−５−アセチルアミノ安息香酸
２−アミノ−４−スルホ安息香酸
２−アミノ−５−スルホ安息香酸
４−アミノ−２，５−ジメチルベンゼンスルホ
ン酸
４−アミノ−２，５−ジメトキシベンゼンスル
ホン酸
４−アミノ−２，５−ジエトキシベンゼンスル
ホン酸
４−アミノ−２−メチル−５−メトキシベンゼ
ンスルホン酸
４−アミノ−２−メチル−５−エトキシベンゼ
ンスルホン酸
２−アミノ−５−メチルベンゼン−１，４−ジ
スルホン酸
２−アミノ−５−メトキシベンゼン−１，４−
ジスルホン酸
２−アミノ−５−エトキシベンゼン−１，４−
ジスルホン酸
２−アミノ−５−アセチルアミノベンゼン−
１，４−ジスルホン酸
２−アミノ−５−プロピオニルアミノベンゼン
−１，４−ジスルホン酸
２−アミノナフタレン−１−スルホン酸
２−アミノナフタレン−１，５−ジスルホン酸
２−アミノナフタレン−１，７−ジスルホン酸
２−アミノナフタレン−１，５，７−トリスル
ホン酸
２−アミノナフタレン−３，６−ジスルホン酸
２−アミノナフタレン−３，８−ジスルホン酸
２−アミノナフタレン−３，６，８−トリスル
ホン酸
等をあげることができる。
本発明による新規な化合物は繊維反応性を有
し、セルロース繊維からなる材料、天然又は合成
ポリアミド繊維、ポリウレタン繊維及び皮革の染
色及び捺染に対して非常に良好な性質を有する。
セルロース繊維とは好ましくは木綿及び再生セ
ルロースが例示されるが他の植物繊維、例えばリ
ネン、大麻、黄麻も含まれる。ポリアミド繊維と
しては天然並びに合成繊維例えば羊毛及び別の動
物毛、絹、ポリアミド−６，６、ポリアミド−
６、ポリアミド−11、又はポリアミド−４などが
例示される。
本発明化合物は特にセルロース繊維の染色およ
び捺染に有用であり、染色およ捺染は通常の反応
染料について行われている通常の方法により実施
される。
即ち、吸尽法の場合、炭酸ソーダ、第三リン酸
ソーダ、苛性ソーダ等の酸結合剤の存在下に芒硝
または食塩を加えた染浴で比較的低い温度で行わ
れる。また、捺染法による染色もでき例えば重炭
酸ソーダ、炭酸ソーダ、第三リン酸ソーダ、苛性
ソーダ等の酸結合剤と尿素および糊剤好ましくは
アルギン酸ソーダ等を含む色糊を繊維に印捺し、
中間乾燥後100〜200℃で蒸熱または乾熱すること
により行なわれる。
更に本発明の染色は連続法により行われてもよ
いし、コールド パツド バツチ染色も可能であ
る。
本発明による新規化合物は染色ストツク液及び
捺染ペースト液中で、又アルカリの存在下で物理
的、化学的に優れた安定性を示し、通常の染色及
び捺染において非常に良好な親和性ときわめて優
れたビルドアツプ性を有する。吸尽染色において
は、比較的浴比及び染色温度等の影響を受けにく
く、再現性よく均染性に優れた染色物を与える。
本発明の化合物により得られる染色物あるいは
捺染物は高い着色力と優れた光沢を有しており、
諸堅牢度、特に塩素堅牢度、耐光堅牢度、汗日光
堅牢度に優れている。
特開昭57−42986号公報にはトリアジンの縮合
成分として一般式（）の化合物を用いた染料が
記載されているが、本発明化合物を繊維材料の染
色及び捺染に用いた場合、対応するそれらの染料
に比べ、アルカリ安定性が良好であり、吸尽染色
において高い吸尽率および固着率を示しまた捺染
でも高い固着率を示すので、濃度の高い染色物を
得ることができるのみならず、同時にウオツシユ
オフ性もすぐれており、未固着染料の除去が簡単
にできると言う大きな利点を有している。
次に本発明を実施例によつて説明する。文中、
部は重量部を示す。
実施例 １
２−（β−スルフアートエチルスルホニル）ア
ニリン20部を水200部にPH５で溶解した液に、45
〜50℃で硫酸ジエチル46部を加え、20％炭酸ナト
リウム水溶液でPH５〜６に調整しながら、同温度
で10時間撹拌すると、２−（β−スルフアートエ
チルスルホニル）−Ｎ−エチルアニリンが65％の
収率で得られる。
この水溶液を20〜25℃に冷却した後、塩化シア
ヌル12部を加え、20％炭酸ナトリウム水溶液でPH
５〜６に調整しながら５時間撹拌する。次いで、
７−アミノ−４−ヒドロキシ−３−（４−メトキ
シ−２−スルホフエニルアゾ）ナフタレン−２−
スルホン酸29部を水300部にPHで溶解した液を加
え、35〜40℃に昇温し、PH５〜６に調整しながら
同温度で５時間撹拌する。次いで、塩化ナトリウ
ム100部を加えて結晶を析出させ、吸引過し、
洗浄した後60℃で乾燥して、次式(1)の化合物を得
た。
参考例 １
式(1)で示される化合物0.3部を200部の水に溶解
し芒硝20部を加え、木綿10部を加えて60℃に昇温
する。ついで30分経過後、炭酸ソーダ４部を加え
同温度で１時間染色する。染色終了後、水洗、ソ
ーピングを行つて諸堅牢度のすぐれた緋色の濃度
の高い染色物が得られた。
実施例１と同様の方法で次表の構造の化合物を
合成し、これを用いて参考例１の方法で木綿を染
色すると同様な性質をもつた表に示す色相の染色
物が得られた。
The present invention relates to fiber-reactive compounds useful for dyeing and printing cellulose fibers, natural or synthetic polyamide fibers, polyurethane fibers or leather. More specifically, the present invention provides the following general formula () in the form of a free acid: (In the formula, D is 1, 2 or 3 from the group of methyl group, ethyl group, methoxy group, ethoxy group, acetylamino group, propionylamino group, succinylamino group, maleylamino group, sulfonic acid group and carboxyl group) represents a phenyl group substituted with 1, 2 or 3 substituents, or a naphthyl group substituted with 1, 2 or 3 sulfonic acid groups.X represents β-sulfatoethyl, β-thiosulfatoethyl, β - Phosphatoethyl, β-chloroethyl or vinyl; Y represents a hydrogen atom, a chlorine atom or a sulfonic acid group; Z represents a hydrogen atom or a methyl group; R represents a lower alkyl group having up to 4 carbon atoms; ) relates to a bifunctional fiber-reactive compound represented by The compounds of the invention are present in the form of the free acid or in the form of its salts, in particular the alkali metal and alkaline earth metal salts, especially the sodium, potassium, calcium salts. When the compounds of the invention are used for dyeing and printing textile materials, alkali metal salts are particularly preferred. The compound of the present invention can be produced, for example, in the following manner. An aromatic amine represented by the following general formula () D-NH 2 () (in the formula, D has the above-mentioned meaning) is diazotized by a conventional method in an aqueous medium to form 7-amino-4-hydroxynaphthalene-
N-acylated product or N-methyl-N-acylated product of 2-sulfonic acid, a temperature of 0°C to 30°C, PH
After performing the coupling reaction while adjusting the pH to 5 to 9, heat the mixture at 50°C to
Hydrolyzing the acyl group at a temperature of 100℃ gives the formula ()
A monoazo compound represented by is obtained. (In the formula, D and Z have the above-mentioned meanings.) Then, the compound of formula () is incubated in an aqueous medium at a temperature of 0.
℃ to 30℃, while adjusting the pH to 7.
Primary condensation with cyanuric chloride yields the dichlorotriazinyl compound, followed by general formula () (In the formula, R, X, and Y have the above-mentioned meanings.) The compound represented by
A compound of general formula () can be obtained by secondary condensation while adjusting the pH to 4 to 7. Alternatively, the compound of general formula () is first condensed with cyanuric chloride in an aqueous medium at a temperature of 0°C to 30°C while adjusting the pH to 3 to 7, and then at a temperature of 20°C to 50°C, PH4 to 7 The compound of the general formula () can also be obtained by secondarily condensing the monoazo compound of the general formula () while adjusting. Alternatively, 7-amino-4-hydroxynaphthalene-2-sulfonic acid or 7-N-methylamino-4-hydroxynaphthalene-2-sulfonic acid and a compound of formula () in any order can be initially reacted in an aqueous medium. Adjust to PH3 to PH7 at a temperature of 0℃ to 30℃, and secondarily adjust to a temperature of 20℃ to 60℃.
While adjusting the pH to 4 to 7, it is condensed with cyanuric chloride to form the general formula () (In the formula, R, X, Y, and Z have the above-mentioned meanings.) To obtain a monochlorotriazinyl compound,
Subsequently, the compound of general formula () can also be obtained by coupling with a diazonium salt of an aromatic amine represented by general formula () at a temperature of 0°C to 30°C while adjusting the pH to 5 to 9. The compound represented by the general formula () is the following general formula () (In the formula, X and Y have the above-mentioned meanings.) Alkylation of the compound represented by the above with alkyl chloride, alkyl bromide, alkyl iodide, dialkyl sulfate, alkyl p-toluenesulfonate, etc. having the corresponding number of carbon atoms. Depending on the agent, PH at a temperature of 20℃ to 80℃
It can be obtained by alkylation while adjusting the pH to 4 to 7. Examples of aromatic amines represented by the general formula () include: 2-aminobenzenesulfonic acid 2-amino-5-methylbenzenesulfonic acid 2-amino-5-methoxybenzenesulfonic acid 2-amino-5-ethoxybenzenesulfone Acids 2-amino-5-acetylaminobenzenesulfonic acid 2-amino-5-propionylaminobenzenesulfonic acid 2-amino-5-succinylaminobenzenesulfonic acid 2-amino-5-maleynylaminobenzenesulfonic acid 2-amino- 4-methoxybenzenesulfonic acid 2-amino-4-ethoxybenzenesulfonic acid 2-amino-4-acetylaminobenzenesulfonic acid 2-amino-4-pyrropionylaminobenzenesulfonic acid 2-amino-4-succinylaminobenzenesulfone Acids 2-amino-4-maleynylaminobenzenesulfonic acid 3-amino-4-methylbenzenesulfonic acid 3-amino-4-methoxybenzenesulfonic acid 3-amino-4-ethoxybenzenesulfonic acid 4-amino-3-methyl Benzenesulfonic acid 4-amino-3-methoxybenzenesulfonic acid 4-amino-3-ethoxybenzenesulfonic acid 2-aminobenzene-1,4-disulfonic acid 2-aminobenzene-1,5-disulfonic acid 2-aminobenzoic acid 2-amino-4-methoxybenzoic acid 2-amino-5-methoxybenzoic acid 2-amino-4-acetylaminobenzoic acid 2-amino-5-acetylaminobenzoic acid 2-amino-4-sulfobenzoic acid 2-amino -5-sulfobenzoic acid 4-amino-2,5-dimethylbenzenesulfonic acid 4-amino-2,5-dimethoxybenzenesulfonic acid 4-amino-2,5-diethoxybenzenesulfonic acid 4-amino-2-methyl -5-methoxybenzenesulfonic acid 4-amino-2-methyl-5-ethoxybenzenesulfonic acid 2-amino-5-methylbenzene-1,4-disulfonic acid 2-amino-5-methoxybenzene-1,4-
Disulfonic acid 2-amino-5-ethoxybenzene-1,4-
Disulfonic acid 2-amino-5-acetylaminobenzene-
1,4-disulfonic acid 2-amino-5-propionylaminobenzene-1,4-disulfonic acid 2-aminonaphthalene-1-sulfonic acid 2-aminonaphthalene-1,5-disulfonic acid 2-aminonaphthalene-1,7 -Disulfonic acid 2-Aminonaphthalene-1,5,7-trisulfonic acid 2-Aminonaphthalene-3,6-disulfonic acid 2-Aminonaphthalene-3,8-disulfonic acid 2-Aminonaphthalene-3,6,8- Examples include trisulfonic acid. The novel compounds according to the invention are fiber-reactive and have very good properties for dyeing and printing materials made of cellulose fibers, natural or synthetic polyamide fibers, polyurethane fibers and leather. Cellulose fibers are preferably exemplified by cotton and regenerated cellulose, but also include other vegetable fibers such as linen, hemp, and jute. Polyamide fibers include natural and synthetic fibers such as wool and other animal hairs, silk, polyamide 6,6, polyamide
Examples include polyamide-6, polyamide-11, and polyamide-4. The compounds of the present invention are particularly useful for dyeing and printing cellulose fibers, and dyeing and printing are carried out by conventional methods used for conventional reactive dyes. That is, in the case of the exhaust method, it is carried out at a relatively low temperature in a dye bath containing mirabilite or common salt in the presence of an acid binder such as soda carbonate, tribasic sodium phosphate, or caustic soda. Dyeing can also be carried out by a printing method, for example, by printing a colored paste containing an acid binder such as bicarbonate of soda, sodium carbonate, tribasic sodium phosphate, or caustic soda, urea, and a sizing agent, preferably sodium alginate, on the fiber.
After intermediate drying, it is carried out by steaming or dry heating at 100 to 200°C. Furthermore, the dyeing of the present invention may be carried out by a continuous method, or cold pad batch dyeing is also possible. The novel compound according to the invention exhibits excellent physical and chemical stability in dyeing stocks and printing pastes and in the presence of alkalis, and has very good affinity and excellent stability in conventional dyeing and printing. It has excellent build-up properties. In exhaust dyeing, it is relatively unaffected by the bath ratio, dyeing temperature, etc., and produces dyed products with good reproducibility and excellent level dyeing properties. The dyed or printed material obtained using the compound of the present invention has high tinting strength and excellent gloss.
It has excellent fastness properties, especially chlorine fastness, light fastness, and sweat/sunlight fastness. JP-A-57-42986 describes a dye using a compound of the general formula () as a condensation component of triazine, but when the compound of the present invention is used for dyeing and printing textile materials, the corresponding dyes It has better alkali stability than dyes of At the same time, it has excellent wash-off properties and has the great advantage that unfixed dye can be easily removed. Next, the present invention will be explained with reference to examples. In the text,
Parts indicate parts by weight. Example 1 20 parts of 2-(β-sulfatoethylsulfonyl)aniline was dissolved in 200 parts of water at pH 5, and 45
Adding 46 parts of diethyl sulfate at ~50°C and stirring at the same temperature for 10 hours while adjusting the pH to 5-6 with a 20% aqueous sodium carbonate solution yields 2-(β-sulfatoethylsulfonyl)-N-ethylaniline. Obtained with a yield of 65%. After cooling this aqueous solution to 20-25℃, 12 parts of cyanuric chloride was added, and the pH was adjusted with 20% sodium carbonate aqueous solution.
Stir for 5 hours while adjusting the temperature to 5-6. Then,
7-amino-4-hydroxy-3-(4-methoxy-2-sulfophenylazo)naphthalene-2-
A solution prepared by dissolving 29 parts of sulfonic acid in 300 parts of water at a pH value is added, the temperature is raised to 35-40°C, and the mixture is stirred at the same temperature for 5 hours while adjusting the pH to 5-6. Next, 100 parts of sodium chloride was added to precipitate crystals, and the mixture was filtered by suction.
After washing and drying at 60°C, a compound of the following formula (1) was obtained. Reference Example 1 Dissolve 0.3 parts of the compound represented by formula (1) in 200 parts of water, add 20 parts of Glauber's Salt, add 10 parts of cotton, and raise the temperature to 60°C. After 30 minutes, 4 parts of soda carbonate is added and dyed at the same temperature for 1 hour. After dyeing, washing and soaping were carried out to obtain a scarlet dyed product with excellent color fastness and high density. Compounds having the structures shown in the following table were synthesized in the same manner as in Example 1, and when cotton was dyed using the same in the method of Reference Example 1, dyed products with similar properties and the hues shown in the table were obtained.
【表】【table】
【表】【table】
【表】
実施例 １
２−（β−スルフアートエチルスルホニル）ア
ニリン20部を水200部にPH５で溶解した液に、30
〜35℃で硫酸ジメチル38部を加え、20％炭酸ナト
リウム水溶液でPH５〜６に調整しながら、同温度
で10時間撹拌すると、２−（β−スルフアートエ
チルスルホニル）−Ｎ−メチルアニリンが54％の
収率で得られる。この水溶液を20〜25℃に冷却し
た後、塩化シアヌル10部を加え、20％炭酸ナトリ
ウム水溶液でPH５〜６に調整しながら４時間撹拌
する。ついで、７−アミノ−４−ヒドロキシナフ
タレン−２−スルホン酸13部を水100部にPH７に
して溶解した液を加え、30〜35℃でPH５〜６に調
整しながら、５時間撹拌する。ついで０〜５℃ま
で冷却した後、20％炭酸ナトリウム水溶液でPH６
〜７に調整しながら２−アミノ−１，５ナフタレ
ンジスルホン酸16部のジアゾニウム塩を１時間か
けて加える。同温度で３時間撹拌した後、塩化ナ
トリウム80部を加えて結晶を析出させ、吸引過
し、洗浄した後、60℃で乾燥して、次式(2)の化合
物を得た。
参考例 ２
式(2)で示される化合物0.3部を300部の水に溶解
し芒硝30部を加え、木綿10部を加えて70℃に昇温
する。ついで20分経過後、炭酸ソーダ５部を加え
同温度で１時間染色する。染色終了後、水洗、ソ
ーピングを行つて諸堅牢度のすぐれた橙色の濃度
の高い染色物が得られた。
実施例11と同様の方法で次表の構造の化合物を
合成し、これを用いて参考例２の方法で木綿を染
色すると同様な性質をもつた表に示す色相の染色
物が得られた。[Table] Example 1 30 parts of 2-(β-sulfatoethylsulfonyl)aniline was dissolved in 200 parts of water at pH 5.
Adding 38 parts of dimethyl sulfate at ~35°C and stirring at the same temperature for 10 hours while adjusting the pH to 5-6 with a 20% aqueous sodium carbonate solution yields 2-(β-sulfatoethylsulfonyl)-N-methylaniline. Obtained with a yield of 54%. After cooling this aqueous solution to 20-25°C, 10 parts of cyanuric chloride is added, and the mixture is stirred for 4 hours while adjusting the pH to 5-6 with a 20% aqueous sodium carbonate solution. Then, a solution prepared by dissolving 13 parts of 7-amino-4-hydroxynaphthalene-2-sulfonic acid in 100 parts of water to a pH of 7 is added, and the mixture is stirred for 5 hours while adjusting the pH to 5 to 6 at 30 to 35°C. After cooling to 0-5℃, the pH was adjusted to 6 with 20% sodium carbonate aqueous solution.
Add 16 parts of diazonium salt of 2-amino-1,5 naphthalenedisulfonic acid over a period of 1 hour while adjusting the temperature to .about.7. After stirring at the same temperature for 3 hours, 80 parts of sodium chloride was added to precipitate crystals, which were filtered under suction, washed, and dried at 60°C to obtain a compound of the following formula (2). Reference Example 2 Dissolve 0.3 parts of the compound represented by formula (2) in 300 parts of water, add 30 parts of Glauber's salt, add 10 parts of cotton, and raise the temperature to 70°C. After 20 minutes, 5 parts of soda carbonate is added and dyed at the same temperature for 1 hour. After dyeing, washing with water and soaping yielded a highly concentrated orange dyed product with excellent fastness. A compound having the structure shown in the following table was synthesized in the same manner as in Example 11, and when cotton was dyed using the same in the method of Reference Example 2, a dyed product having similar properties and the hue shown in the table was obtained.
Claims (1)
基、エトキシ基、アセチルアミノ基、プロピオニ
ルアミノ基、サクシニルアミノ基、マレイニルア
ミノ基、スルホン酸基及びカルボキシル基の群か
らなる１、２又は３個の置換基により置換されて
いるフエニル基、或いはスルホン酸基１、２又は
３個で置換されているナフチル基を表わす。 Ｘはβ−スルフアートエチル、β−チオスルフ
アートエチル、β−ホスフアートエチル、β−ク
ロルエチル又はビニルを表わし、Ｙは水素原子、
塩素原子又はスルホン酸基を表わし、Ｚは水素原
子又はメチル基を表わす。Ｒは炭素数４までの低
級アルキル基を表わす。） で示されるモノアゾ化合物。[Claims] 1 The following general formula in the form of a free acid: (In the formula, D is 1, 2 or 3 from the group of methyl group, ethyl group, methoxy group, ethoxy group, acetylamino group, propionylamino group, succinylamino group, maleylamino group, sulfonic acid group and carboxyl group) represents a phenyl group substituted with 1, 2 or 3 substituents, or a naphthyl group substituted with 1, 2 or 3 sulfonic acid groups. X is β-sulfatoethyl, β-thiosulfatoethyl, β - Phosphatoethyl, β-chloroethyl or vinyl, Y is a hydrogen atom,
It represents a chlorine atom or a sulfonic acid group, and Z represents a hydrogen atom or a methyl group. R represents a lower alkyl group having up to 4 carbon atoms. ) A monoazo compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11345782A JPS594653A (en) | 1982-06-29 | 1982-06-29 | Novel monoazo compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11345782A JPS594653A (en) | 1982-06-29 | 1982-06-29 | Novel monoazo compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS594653A JPS594653A (en) | 1984-01-11 |
| JPH0368071B2 true JPH0368071B2 (en) | 1991-10-25 |
Family
ID=14612719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11345782A Granted JPS594653A (en) | 1982-06-29 | 1982-06-29 | Novel monoazo compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS594653A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3624136A1 (en) * | 1985-09-30 | 1987-04-09 | Hoechst Ag | WATER-SOLUBLE AZO COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS DYES |
| US4902786A (en) * | 1986-07-17 | 1990-02-20 | Hoechst Aktiengesellschaft | Phenylazonaphthol or naphthylazonaphthol compounds containing a fibre-reactive aminophenylamino-substituted halogen-s-triazinylamino group and a fibre-reactive group of the vinylsulfone series, suitable as dyestuffs |
| DE3704660A1 (en) * | 1987-02-14 | 1988-08-25 | Hoechst Ag | WATER-SOLUBLE AZO COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS DYES |
| JP2524979Y2 (en) * | 1990-04-23 | 1997-02-05 | 鐘紡株式会社 | Stretched printed fabric |
| US5350838A (en) * | 1993-02-08 | 1994-09-27 | Hoechst Celanese Corporation | High temperature process for preparing fiber reactive dyes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5742986A (en) * | 1980-08-29 | 1982-03-10 | Nippon Kayaku Kk | Dyeing of natural or synthetic fiber by using reactive monoazo compound |
| JPS5789679A (en) * | 1980-11-26 | 1982-06-04 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
-
1982
- 1982-06-29 JP JP11345782A patent/JPS594653A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5742986A (en) * | 1980-08-29 | 1982-03-10 | Nippon Kayaku Kk | Dyeing of natural or synthetic fiber by using reactive monoazo compound |
| JPS5789679A (en) * | 1980-11-26 | 1982-06-04 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS594653A (en) | 1984-01-11 |
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