JPH04109B2 - - Google Patents
Info
- Publication number
- JPH04109B2 JPH04109B2 JP57134114A JP13411482A JPH04109B2 JP H04109 B2 JPH04109 B2 JP H04109B2 JP 57134114 A JP57134114 A JP 57134114A JP 13411482 A JP13411482 A JP 13411482A JP H04109 B2 JPH04109 B2 JP H04109B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrogen atom
- alkyl group
- parts
- general formula
- 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 monoazo compound Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 238000004043 dyeing Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000012209 synthetic fiber Substances 0.000 claims description 8
- 229920002994 synthetic fiber Polymers 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 239000000835 fiber Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- DZRZHFOFVWAKGT-UHFFFAOYSA-N 3,5-dinitrothiophen-2-amine Chemical compound NC=1SC([N+]([O-])=O)=CC=1[N+]([O-])=O DZRZHFOFVWAKGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- SXPXTTKGVYQPAM-UHFFFAOYSA-N n-(1-ethyl-2,2,4-trimethyl-3,4-dihydroquinolin-7-yl)acetamide Chemical compound CC(=O)NC1=CC=C2C(C)CC(C)(C)N(CC)C2=C1 SXPXTTKGVYQPAM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical group C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101000996935 Homo sapiens Putative oxidoreductase GLYR1 Proteins 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 102100034301 Putative oxidoreductase GLYR1 Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明は新規なモノアゾ化合物及びそれを用い
る合成繊維類の染色または捺染法に関するもので
ある。より詳しくは、本発明は水不溶性モノアゾ
化合物及びそれを用いて、ポリエステル繊維、ポ
リアミド繊維などの合成繊維類を青〜緑色に染色
または捺染する方法に関するものである。
すなわち、本発明は、一般式（）
（式中、Ｘは水素原子、ニトロ基、低級アルキル
基又は更に置換されていてもよいフエニル基、Ｙ
は低級アルキル基、更に置換されていてもよいフ
エニル基、ニトロ基、シアノ基、低級アルコキシ
カルボニル基又はカルボンアミド基、Ｚは水素原
子、ハロゲン原子、アルキル基、アシルアミノ
基、ベンゾイルアミノ基またはアルキルスルホニ
ルアミノ基、R1、R2、R3、R4は各々独立に水素
原子またはアルキル基、R5は水素原子、アルキ
ル基、置換アルキル基、アルケニル基、シクロア
ルキル基、アラルキル基またはフエニル基を表わ
す。）
で示されるモノアゾ化合物及びそれを用いること
を特徴とする合成繊維類の染色または捺染法であ
る。
本発明における低級とは炭素数が１〜４である
ことを示す。一般式（）で示される化合物にお
いて、有利には、Ｘは水素原子、Ｙはニトロ基、
Ｚは水素原子、塩素原子、臭素原子、低級アシル
アミノ基、ベンゾイルアミノ基、低級アルキルス
ルホニルアミノ基、R1、R2、R3、R4は水素原
子、メチル基が好ましい。
本発明のモノアゾ化合物は、ポリエステル繊
維、ポリアミド繊維などの合成繊維用の分散染料
として種々の特性、例えば、染着性、染浴安定
性、PH安定性、ビルドアツプ性などが優れ、更に
水、洗濯、マサツ、昇華、日光などの諸堅牢度特
に後加工後の堅牢度にも優れた性能を示す。
本発明において一般式（）で示されるモノア
ゾ化合物は、一般式（）
（式中、Ｘ、Ｙは前記の意味を表わす。）
で示されるアミン化合物を公知の方法、例えば特
開昭48−84121号公報に記載されている方法でジ
アゾ化し、一般式（）、
（式中、Ｚ、R1、R2、R3、R4、R5は前記の意味
を表わす。）
で示される化合物とカツプリングさせることによ
つて製造できる。
一般式（）で示される化合物は、公知の方
法、例えば、ヘミツシエ・ベリヒテ第98巻、3571
頁（1965年）、及び第99巻94頁（1966年）、特開昭
49−48658号公報に記載されている方法で製造で
きる。
一般式（）で示される化合物は、公知の方法
例えば、特公昭47−34680号公報に記載されてい
る方法で製造される。
本発明のモノアゾ化合物は、具体的には、例え
ば次のようにして製造できる。
一般式（）で示されるアミン化合物を、硫
酸、塩酸などの鉱酸、又は酢酸、プロピオン酸な
どの有機酸、又はそれらの混合溶媒に溶解又は分
散させ、冷時好ましくは５℃以下でニトロシル硫
酸を用いてジアゾ化する。一方、一般式（）で
示される化合物を、硫酸、塩酸などの鉱酸、又は
酢酸、プロピオン酸などの有機酸、又はメタノー
ル、エタノールなどの有機溶媒、又はそれらの混
合溶媒に溶解し、これに前記ジアゾニウム化合物
を冷時好ましくは10℃以下で添加し、カツプリン
グさせる。反応終了後、析出した結晶を別し
て、一般式（）で表わされるモノアゾ化合物が
得られる。このとき、場合によつては、PHを１〜
５に調節するとカツプリングが速やかに起るので
好ましい。
一般式（）で示されるアミン化合物としては
具体的には次のものがあげられる。
２−アミノ−３，５−ジニトロチオフエン
２−アミノ−３，４，５−トリニトロチオフエ
ン
２−アミノ−３−ニトロ−５−メトキシカルボ
ニルチオフエン
２−アミノ−３，５−ジニトロ−４−メチルチ
オフエン
２−アミノ−３，５−ジニトロ−４−エトキシ
カルボニルチオフエン
一般式（）で示される化合物としては具体的
には次のものがあげられる。
１，２，３，４−テトラハイドロキノリン
２，２，４−トリメチル−１，２，３，４−テ
トラハイドロキノリン
１−エチル−２，２，４−トリメチル−１，
２，３，４−テトラハイドロキノリン
１−ブチル−２，７−ジメチル−１，２，３，
４−テトラハイドロキノリン
１−（２−ヒドロキシエチル）−２，２，４，７
−テトラメチル−１，２，３，４−テトラハイド
ロキノリン
１−（２−シアノエチル）−２，２，４−トリメ
チル−７−クロロ−１，２，３，４−テトラハイ
ドロキノリン
１−ベンジル−２，７−ジメチル−１，２，
３，４−テトラハイドロキノリン
１−シクロヘキシル−２，２，４−トリメチル
−１，２，３，４−テトラハイドロキノリン
１−エチル−２，２，４−トリメチル−１，
２，３，４−テトラハイドロキノリン
１−アリル−２，２，４−トリメチル−１，
２，３，４−テトラハイドロキノリン
１−（２−アセトキシエチル）−２，２，４−ト
リメチル−７−アセチルアミノ−１，２，３，４
−テトラハイドロキノリン
１−プロピル−２，２，４−トリメチル−７−
メチルスルホニルアミノ−１，２，３，４−テト
ラハイドロキノリン
１−エチル−２，２，４−トリメチル−７−ベ
ンゾイルアミノ−１，２，３，４−テトラハイド
ロキノリン
１−フエネチル−２，４，８−トリメチル−７
−プロピオニルアミノ−１，２，３，４−テトラ
ハイドロキノリン
本発明における合成繊維類としては、ポリエス
テル系、ポリアミド系繊維、ポリオレフイン系繊
維、セルロースエステル系繊維又はこれらの繊維
の混紡品を挙げることができる。
本発明の化合物は特にポリエステル系繊維に対
して優れた染色特性を発揮する。
本発明のモノアゾ化合物を用いて合成繊維類を
染色するにあたつては、まず一般式（）で示さ
れるモノアゾ化合物の一種又は二種以上を適当な
分散剤と共に水性媒体中で微細な粒子に粉砕し、
分散化させる。分散化した染料は、そのままの液
状あるいはスプレー乾燥等によつて粉末状として
用いられる。染色はそれ自体公知の方法により、
分散化した染料を水性媒体中に分散させて染浴を
調製し、合成繊維を浸漬して、加圧下105℃以下、
好ましくは、110〜140℃で染色するか、０−フエ
ニルフエノールやトルクロロベンゼン等のキヤリ
ヤーの存在下で比較的高温、例えば水の沸騰状態
で染色するか、染料分散液を布にパツデングし、
150〜230℃で30〜120秒間の乾熱処理をするいわ
ゆるサーモゾル染色法で染色するか、捺染の場合
は、染料分散液を適当な糊剤と共に練り合わせ、
これを布にパツデングし、スチーミング又はサー
モゾル処理をして染色を行なうことができる。
又、トリクロロエチレンやパークロロエチレン等
の有機溶剤を染色媒体した溶剤染色法も可能であ
る。
次に本発明を実施例により、更に詳細に説明す
るが、本発明はそれらの実施例によつて限定され
るものではない。文中、部及び％は特記しない限
りそれぞれ重量部、重量％を意味する。
実施例 １
プロピオン酸／酢酸（14／86容量部）150部に
43％ニトロシル硫酸35.4部を加え、０℃に冷却す
る。これに、２−アミノ−３，５−ジニトロチオ
フエン8.9部を０℃以下で徐々に加え、３時間同
温度で保温撹拌してジアゾ化する。一方、１−エ
チル−２，２，４−トリメチル−７−アセチルア
ミノ−１，２，３，４−テトラハイドロキノリン
26.0部をメタノール100部に溶解し、これに前記
ジアゾニウム溶液を氷で０℃以下に冷却しながら
加える。この後、PHを２〜５に調整してカツプリ
ングを終了させる。析出した結晶を別、水洗、
乾燥して式（）
λmax635nｍ（DMF中）
の化合物25.3部が得られた。
収率55％
２−アミノ−３，５−ジニチロチオフエンは、
特開昭49−48658号公報に記載されている方法に
より合成した。一方の１−エチル−２，２，４−
トリメチル−７−アセチルアミノ−１，２，３，
４−テトラハイドロキノリンは、特公昭47−
34680号公報に記載されている方法により合成し
た。
実施例 ２
式(1)のモノアゾ化合物１部をナフタレンスルホ
ン酸のホルマリン縮合物１部、リグニンスルホン
酸ソーダ１部と共に微粒化分散し、これと高級ア
ルコール硫酸エステル３部を水3000部に均一に分
散させて染浴を調製する。この染浴にポリエステ
ル加工糸織物100部を浸漬し、130℃で60分間染色
を行なつた後、染色物をカセイソーダ３部、ハイ
ドロサルフアイト３部、ベタイン型両性界面活性
剤３部と水3000部からなる処理液で、85℃で10分
間還元洗浄処理を行なつた。その後、水洗、乾燥
して濃度の高い鮮明な青緑色の染色物が得られ
た。この染色物は、昇華、耐光、水、洗濯の堅牢
度に優れた性能を示した。
実施例 ３
２−アミノ−３，５−ジニトロチオフエンおよ
び１−ペンチル−２，２，４−トリメチル−７−
アセチルアミノ−１，２，３−４−テトラハイド
ロキノリンを用い、実施例１と同様にして式(2)の
モノアゾ化合物を合成した。
実施例 ４
式(2)のモノアゾ化合物１部をナフタレンスルホ
ン酸のホルマリン縮合物２部と共に微粒化分散
し、得られた染料組成物を下記組成の捺染元糊95
部に加え、よく練り合わせて色糊を調製する。
（捺染元糊）
12％メイプロガムNP60（ローカストビーンガム）
63部
塩素酸ソーダ 0.6部
酒石酸 0.4部
水 36部
計 100部
この色糊をポリエステル加工糸織物に印捺し、
乾燥後、高圧スチーマー（温度130〜135℃、ゲー
ジ圧３〜４Kg／cm2）にて30分間スチーミングし
た。この後、水洗、乾燥して、実施例２と同様に
して還元洗浄処理を行ない、水洗、乾燥して、濃
度の高い鮮明な青緑色の染色物が得られた。この
染色物は、昇華、耐光、水、洗濯の堅牢度に優れ
た性能を示した。
以下、実施例１と同様にして表１のモノアゾ化
合物を合成し、各々、実施例２と同様にして染色
を行ない表１に示される結果を得た。表中、色相
はポリエステル繊維上の色相を示す。
The present invention relates to a novel monoazo compound and a method for dyeing or printing synthetic fibers using the same. More specifically, the present invention relates to a water-insoluble monoazo compound and a method for dyeing or printing synthetic fibers such as polyester fibers and polyamide fibers in blue to green colors using the same. That is, the present invention provides the general formula () (wherein, X is a hydrogen atom, a nitro group, a lower alkyl group, or a phenyl group that may be further substituted, Y
is a lower alkyl group, an optionally substituted phenyl group, a nitro group, a cyano group, a lower alkoxycarbonyl group, or a carbonamide group; Z is a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, a benzoylamino group, or an alkylsulfonyl group; amino group, R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or an alkyl group; R 5 represents a hydrogen atom, an alkyl group, a substituted alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, or a phenyl group; represent ) A method for dyeing or printing synthetic fibers characterized by using the monoazo compound shown in the following formula and using the monoazo compound. In the present invention, lower means having 1 to 4 carbon atoms. In the compound represented by the general formula (), X is preferably a hydrogen atom, Y is a nitro group,
Z is preferably a hydrogen atom, a chlorine atom, a bromine atom, a lower acylamino group, a benzoylamino group, a lower alkylsulfonylamino group, and R 1 , R 2 , R 3 and R 4 are preferably a hydrogen atom or a methyl group. The monoazo compound of the present invention has excellent properties as a disperse dye for synthetic fibers such as polyester fibers and polyamide fibers, such as dyeing properties, dye bath stability, PH stability, and build-up properties, and is also resistant to water and washing. It exhibits excellent fastness to various types of light, such as maturation, sublimation, and sunlight, especially after post-processing. In the present invention, the monoazo compound represented by the general formula () is the monoazo compound represented by the general formula () (In the formula, X and Y represent the above-mentioned meanings.) The amine compound represented by the formula is diazotized by a known method, for example, the method described in JP-A-48-84121, and the general formula (), (In the formula, Z, R 1 , R 2 , R 3 , R 4 and R 5 have the above-mentioned meanings.) It can be produced by coupling with a compound represented by the following formula. The compound represented by the general formula () can be prepared by a known method, for example, Hemitsche Berichte Vol. 98, 3571.
Page (1965), and Vol. 99, p. 94 (1966), Tokukai Sho.
It can be produced by the method described in Japanese Patent No. 49-48658. The compound represented by the general formula () can be produced by a known method, for example, the method described in Japanese Patent Publication No. 47-34680. Specifically, the monoazo compound of the present invention can be produced, for example, as follows. An amine compound represented by the general formula () is dissolved or dispersed in a mineral acid such as sulfuric acid or hydrochloric acid, or an organic acid such as acetic acid or propionic acid, or a mixed solvent thereof. Diazotize using. On the other hand, a compound represented by the general formula () is dissolved in a mineral acid such as sulfuric acid or hydrochloric acid, or an organic acid such as acetic acid or propionic acid, or an organic solvent such as methanol or ethanol, or a mixed solvent thereof. The diazonium compound is added cold, preferably below 10°C, and coupled. After the reaction is completed, the precipitated crystals are separated to obtain a monoazo compound represented by the general formula (). At this time, depending on the case, the pH may be adjusted to 1 or more.
Adjustment to 5 is preferable because coupling occurs quickly. Specific examples of the amine compound represented by the general formula () include the following. 2-amino-3,5-dinitrothiophene 2-amino-3,4,5-trinitrothiophene 2-amino-3-nitro-5-methoxycarbonylthiophene 2-amino-3,5-dinitro-4 -Methylthiophene 2-Amino-3,5-dinitro-4-ethoxycarbonylthiophene Specific examples of the compound represented by the general formula () include the following. 1,2,3,4-tetrahydroquinoline 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline 1-ethyl-2,2,4-trimethyl-1,
2,3,4-tetrahydroquinoline 1-butyl-2,7-dimethyl-1,2,3,
4-tetrahydroquinoline 1-(2-hydroxyethyl)-2,2,4,7
-Tetramethyl-1,2,3,4-tetrahydroquinoline 1-(2-cyanoethyl)-2,2,4-trimethyl-7-chloro-1,2,3,4-tetrahydroquinoline 1-benzyl- 2,7-dimethyl-1,2,
3,4-tetrahydroquinoline 1-cyclohexyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline 1-ethyl-2,2,4-trimethyl-1,
2,3,4-tetrahydroquinoline 1-allyl-2,2,4-trimethyl-1,
2,3,4-tetrahydroquinoline 1-(2-acetoxyethyl)-2,2,4-trimethyl-7-acetylamino-1,2,3,4
-Tetrahydroquinoline 1-propyl-2,2,4-trimethyl-7-
Methylsulfonylamino-1,2,3,4-tetrahydroquinoline 1-ethyl-2,2,4-trimethyl-7-benzoylamino-1,2,3,4-tetrahydroquinoline 1-phenethyl-2,4 ,8-trimethyl-7
-Propionylamino-1,2,3,4-tetrahydroquinoline Examples of the synthetic fibers in the present invention include polyester fibers, polyamide fibers, polyolefin fibers, cellulose ester fibers, and blends of these fibers. can. The compound of the present invention exhibits excellent dyeing properties particularly for polyester fibers. When dyeing synthetic fibers using the monoazo compound of the present invention, first, one or more monoazo compounds represented by the general formula () are pulverized into fine particles in an aqueous medium together with a suitable dispersant. crush,
Decentralize. The dispersed dye can be used in a liquid form as it is or in a powder form by spray drying or the like. Dyeing is done by a method known per se.
A dye bath is prepared by dispersing the dispersed dye in an aqueous medium, and the synthetic fibers are immersed in the dye bath and heated at 105℃ or less under pressure.
Preferably, the fabric is dyed at 110 to 140°C, or in the presence of a carrier such as 0-phenylphenol or trichlorobenzene at a relatively high temperature, such as boiling water, or the dye dispersion is padded onto the fabric.
Dyeing is done by the so-called thermosol dyeing method, which involves dry heat treatment at 150 to 230°C for 30 to 120 seconds, or in the case of textile printing, the dye dispersion is kneaded with a suitable sizing agent.
This can be applied to cloth and dyed by steaming or thermosol treatment.
Furthermore, a solvent dyeing method using an organic solvent such as trichlorethylene or perchloroethylene as a dyeing medium is also possible. EXAMPLES Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited by these Examples. In the text, parts and % mean parts by weight and % by weight, respectively, unless otherwise specified. Example 1 Propionic acid/acetic acid (14/86 parts by volume) to 150 parts
Add 35.4 parts of 43% nitrosyl sulfate and cool to 0°C. To this, 8.9 parts of 2-amino-3,5-dinitrothiophene was gradually added at 0° C. or below, and diazotization was carried out by stirring at the same temperature for 3 hours. On the other hand, 1-ethyl-2,2,4-trimethyl-7-acetylamino-1,2,3,4-tetrahydroquinoline
Dissolve 26.0 parts in 100 parts of methanol, and add the diazonium solution to this while cooling with ice to below 0°C. After this, the pH is adjusted to 2 to 5 and the coupling is completed. Separate the precipitated crystals, wash with water,
dry formula () 25.3 parts of a compound with λmax 635 nm (in DMF) were obtained. Yield 55% 2-amino-3,5-dinithylothiophene is
It was synthesized by the method described in JP-A-49-48658. One 1-ethyl-2,2,4-
Trimethyl-7-acetylamino-1,2,3,
4-tetrahydroquinoline was produced by the Special Publication Act in 1972.
It was synthesized by the method described in Publication No. 34680. Example 2 1 part of the monoazo compound of formula (1) was atomized and dispersed together with 1 part of a formalin condensate of naphthalene sulfonic acid and 1 part of sodium ligninsulfonate, and this and 3 parts of higher alcohol sulfate were uniformly added to 3000 parts of water. Disperse and prepare a dyebath. After immersing 100 parts of polyester processed yarn fabric in this dye bath and dyeing at 130°C for 60 minutes, the dyed product was mixed with 3 parts of caustic soda, 3 parts of hydrosulfite, 3 parts of betaine type amphoteric surfactant, and 3000 parts of water. A reduction cleaning treatment was performed at 85° C. for 10 minutes using a treatment solution consisting of Thereafter, it was washed with water and dried to obtain a dyed product with a high density and clear blue-green color. This dyed product showed excellent performance in sublimation, light fastness, water fastness, and washing fastness. Example 3 2-amino-3,5-dinitrothiophene and 1-pentyl-2,2,4-trimethyl-7-
A monoazo compound of formula (2) was synthesized in the same manner as in Example 1 using acetylamino-1,2,3-4-tetrahydroquinoline. Example 4 1 part of the monoazo compound of formula (2) was atomized and dispersed with 2 parts of a formalin condensate of naphthalene sulfonic acid, and the resulting dye composition was mixed into a printing base paste 95 with the following composition.
1. Add to the ingredients and mix well to prepare colored glue. (Printing paste) 12% Maypro Gum NP60 (Locust Bean Gum)
63 parts Sodium chlorate 0.6 parts Tartaric acid 0.4 parts Water 36 parts Total 100 parts This color paste is printed on polyester processed yarn fabric.
After drying, it was steamed for 30 minutes using a high-pressure steamer (temperature 130-135°C, gauge pressure 3-4 Kg/cm 2 ). Thereafter, it was washed with water, dried, and subjected to reduction washing treatment in the same manner as in Example 2, washed with water, and dried to obtain a dyed product with a high density and clear blue-green color. This dyed product showed excellent performance in sublimation, light fastness, water fastness, and washing fastness. Thereafter, the monoazo compounds shown in Table 1 were synthesized in the same manner as in Example 1, and each was dyed in the same manner as in Example 2 to obtain the results shown in Table 1. In the table, the hue indicates the hue on the polyester fiber.
【表】【table】
【表】【table】
Claims (1)
基又は更に置換されていてもよいフエニル基、Ｙ
は低級アルキル基、更に置換されていてもよいフ
エニル基、ニトロ基、シアノ基、低級アルコキシ
カルボニル基又はカルボンアミド基、Ｚは水素原
子、ハロゲン原子、アルキル基、アシルアミノ
基、ベンゾイルアミノ基又はアルキルスルホニル
アミノ基、R1、R2、R3、R4は各々独立に水素原
子またはアルキル基、R5は水素原子、アルキル
基、置換アルキル基、アルケニル基、シクロアル
キル基、アラルキル基またはフエニル基を表わ
す。） で示されるモノアゾ化合物。 ２ 一般式（） （式中、Ｘは水素原子、ニトロ基、低級アルキル
基又は更に置換されていてもよいフエニル基、Ｙ
は低級アルキル基、更に置換されていてもよいフ
エニル基、ニトロ基、シアノ基、低級アルコキシ
カルボニル基又はカルボンアミド基、Ｚは水素原
子、ハロゲン原子、アルキル基、アシルアミノ
基、ベンゾイルアミノ基又はアルキルスルホニル
アミノ基、R1、R2、R3、R4は各々独立に水素原
子又はアルキル基、R5は水素原子、アルキル基、
置換アルキル基、アルケニル基、シクロアルキル
基、アラルキル基又はフエニル基を表わす。） で示される化合物を用いることを特徴とする合成
繊維類の染色または捺染法。[Claims] 1 General formula () (wherein, X is a hydrogen atom, a nitro group, a lower alkyl group, or a phenyl group that may be further substituted, Y
is a lower alkyl group, an optionally substituted phenyl group, a nitro group, a cyano group, a lower alkoxycarbonyl group, or a carbonamide group; Z is a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, a benzoylamino group, or an alkylsulfonyl group; amino group, R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or an alkyl group; R 5 represents a hydrogen atom, an alkyl group, a substituted alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, or a phenyl group; represent ) A monoazo compound represented by 2 General formula () (wherein, X is a hydrogen atom, a nitro group, a lower alkyl group, or a phenyl group that may be further substituted, Y
is a lower alkyl group, an optionally substituted phenyl group, a nitro group, a cyano group, a lower alkoxycarbonyl group, or a carbonamide group; Z is a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, a benzoylamino group, or an alkylsulfonyl group; amino group, R 1 , R 2 , R 3 , R 4 are each independently a hydrogen atom or an alkyl group, R 5 is a hydrogen atom or an alkyl group,
Represents a substituted alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group. ) A method for dyeing or printing synthetic fibers, characterized by using a compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13411482A JPS5924754A (en) | 1982-07-30 | 1982-07-30 | Monoazo compound and dyeing method using same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13411482A JPS5924754A (en) | 1982-07-30 | 1982-07-30 | Monoazo compound and dyeing method using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5924754A JPS5924754A (en) | 1984-02-08 |
| JPH04109B2 true JPH04109B2 (en) | 1992-01-06 |
Family
ID=15120783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13411482A Granted JPS5924754A (en) | 1982-07-30 | 1982-07-30 | Monoazo compound and dyeing method using same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5924754A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105820596B (en) * | 2016-04-22 | 2017-12-22 | 深圳市国华光电科技有限公司 | A kind of tetrahydro chinolines dyestuff, ink and electric moistening display |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4884121A (en) * | 1972-01-28 | 1973-11-08 | ||
| JPS4953222A (en) * | 1972-07-11 | 1974-05-23 |
-
1982
- 1982-07-30 JP JP13411482A patent/JPS5924754A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4884121A (en) * | 1972-01-28 | 1973-11-08 | ||
| JPS4953222A (en) * | 1972-07-11 | 1974-05-23 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5924754A (en) | 1984-02-08 |
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