JPH0358387B2 - - Google Patents
Info
- Publication number
- JPH0358387B2 JPH0358387B2 JP57017266A JP1726682A JPH0358387B2 JP H0358387 B2 JPH0358387 B2 JP H0358387B2 JP 57017266 A JP57017266 A JP 57017266A JP 1726682 A JP1726682 A JP 1726682A JP H0358387 B2 JPH0358387 B2 JP H0358387B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- dye
- represented
- water
- 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
- 239000000835 fiber Substances 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 11
- 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 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- -1 alkali metal salt Chemical class 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- XKTXFHFQGLRJKG-UHFFFAOYSA-N 2-phenoxyethyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OCCOC1=CC=CC=C1 XKTXFHFQGLRJKG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RTTKVNNZRGYCTK-UHFFFAOYSA-N CC=1C=C(O)N(C)C(=O)C=1C#N Chemical compound CC=1C=C(O)N(C)C(=O)C=1C#N RTTKVNNZRGYCTK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- UQBMHYREWDMIHR-UHFFFAOYSA-N N-phenylcarbamic acid 2-phenoxyethyl ester Chemical class C=1C=CC=CC=1OCCOC(=O)NC1=CC=CC=C1 UQBMHYREWDMIHR-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CYTOETGRTXBVRH-UHFFFAOYSA-N ethanol;potassium Chemical compound [K].[K].CCO CYTOETGRTXBVRH-UHFFFAOYSA-N 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 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 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明はポリエステル系繊維用モノアゾ染料に
関するものであり、詳しくはポリエステル系繊維
を鮮明な緑味黄色に染色し、諸堅牢度、特に日光
堅牢度、昇華堅牢度および水堅牢度にすぐれか
つ、染色時の温度安定性およびPH安定性にすぐれ
たモノアゾ染料に関するものである。
以下に本発明を詳細に説明する。
本発明のモノアゾ染料は下記一般式〔〕
（式中、R1はフエニル基、ベンジル基またはフ
エネチル基を表わし、R2はC1〜4アルキル基、
C1〜4アルコキシカルボニルC1〜3アルキル基または
C1〜4アルコキシC1〜4基を表わし、ｎは１または２
である。）
で示されるポリエステル系繊維用モノアゾ染料で
ある。
上記一般式〔〕で示されるモノアゾ染料は、
たとえば、（Ａ）一般式〔〕
（式中、R1およびｎは前記定義に同じ）
で示される化合物を一般式〔〕
Ｘ−R2 …〔〕
（式中、Ｘはハロゲン原子を表わし、R2は前記
定義に同じ）
で示される化合物、または一般式〔〕
Ｄ−SO2R2 …〔〕
（式中、Ｄはフエニル基またはトリル基を表わ
し、R2は前記定義に同じ。）
で示される化合物または一般式〔〕
（R2O）2SO2 …〔〕
（式中、R2は前記定義に同じ）
で示される化合物と反応させることにより、ま
た、(B)一般式〔〕
（式中、R1およびｎは前記定義に同じ）
で示されるアニリン類を常法によりジアゾ化し、
一般式〔〕
（式中、R2は前記定義に同じ）
で示されるピリドン類とカツプリングすることに
より、製造される。
本発明の染料の製造方法(A)によれば、一般式
〔〕で示されるアニリン類を常法によりジアゾ
化し、３−シアノ−６−ヒドロキシ−４−メチル
ピリド−２−オンまたはそのアルカリ金属塩と常
法によりカツプリングさせて一般式〔〕で示さ
れるアゾ化合物を得、次いで得られたアゾ化合物
をクロルベンゼン、ジクロルベンゼン、ニトロベ
ンゼン、ｏ−ニトロトルエン等の芳香族系化合
物、ジメチルホルムアミド等のＮ−アルキルホル
ムアミド、Ｎ−メチルピロリドン等のＮ−アルキ
ルピロリドン、アセトン、メチルエチルケトン等
のケトン類、メタノール、エタノール等のアルコ
ールなどの不活性有機溶媒中でピリジン、ピペリ
ジン、トリエチルアミン等の有機塩基または炭酸
ナトリウム、炭酸カリウム、酸化マグネシウム、
水酸化ナトリウム等の無機塩基の存在下、一般式
〔〕で示されるスルホン酸エステルまたは一般
式〔〕で示されるハロゲン化物、または一般式
〔〕で示される硫酸エステルと、−30℃〜100℃
で反応させることにより一般式〔〕で示される
ピリドン系アゾ染料が純度よく高収率で得られ
る。
本発明の染料の製造方法(B)においてジアゾ成分
として用いられる一般式〔〕で示されるアニリ
ン類は、具体的には、ｏ−、ｍ−、またはｐ−
（フエノキシエトキシカルボニル）アニリン、
ｏ−、ｍ−、またはｐ−（フエノキシエトキシ
エトキシカルボニル）アニリン、
ｏ−、ｍ−、またはｐ−（ベンジルオキシエト
キシカルボニル）アニリン、
ｏ−、ｍ−、またはｐ−（ベンジルオキシエト
キシエトキシカルボニル）アニリン、
ｏ−、ｍ−、またはｐ−（フエネチルオキシエ
トキシカルボニル）アニリン、
ｏ−、ｍ−、またはｐ−（フエネチルオキシエ
トキシエノキシカルボニル）アニリン、
等が挙げられる。
カツプリング成分として用いられる一般式
〔〕で示されるピリドン類は、たとえば、アセ
ト酢酸エステル、シアノ酢酸エステルおよび置換
されていてもよいアルキルアミンを縮合環化する
ことにより得られる。
本発明の後者の製造方法において、ジアゾ化お
よびカツプリング反応は一般に行なわれている方
法が用いられる。例えば、フエノキシエトキシカ
ルボニルアニリン類を濃硫酸と亜硝酸ナトリウム
から調製したニトロシク硫酸に加えてジアゾ化す
るかまたは塩酸水溶液に溶解もしくは懸濁させた
後、亜硝酸ナトリウム水溶液を加えてジアゾ化
し、３−シアノ−４−メチル−６−ヒドロキシ−
ピリドン類を含有する酢酸ナトリウム、炭酸ナト
リウム、水酸化ナトリウム等のアルカリ水溶液中
に加えることにより行なわれる。カツプリング反
応は中性ないしアルカリ性でも行なわれるが、好
ましくは微酸性で行なわれる。
本発明のモノアゾ染料により染色しうる繊維と
しては、ポリエチレンテレフタレート、テレフタ
ル酸と１，４−ビス−（ヒドロキシメチル）シク
ロヘキサンとの重縮合物などよりなるポリエステ
ル繊維、あるいは木綿、絹、羊毛などの天然繊維
と上記ポリエステル繊維との混紡品、混織品が挙
げられる。
本発明の染料を用いてポリエステル繊維を染色
するには、前示一般式〔〕で示される染料が水
に不溶ないし難溶であるので、常法により、分散
剤としてナフタレンスルホン酸とホルムアルデヒ
ドとの縮合物、高級アルコール硫酸エステル、高
級アルキルベンゼンスルホン酸塩などを使用して
水性媒質中に分散させた染色浴または捺染糊を調
製し、浸染または捺染を行なえばよい。例えば浸
染の場合、高温染色法、キヤリヤー染色法、サー
モゾル染色法などの通常の染色処理法を適用すれ
ば、ポリエステル繊維ないしは、その混紡品に堅
牢度のすぐれた染色を施すことができる。その
際、場合により、染色浴にギ酸、酢酸、リン酸あ
るいは硫酸アンモニウムなどのような酸性物質を
添加すれば、さらに好結果が得られる。
また、本発明の前示一般式〔〕で示される染
料は同系統の染料あるいは他系統の染料と併用し
てもよく、このうち前示一般式〔〕で示される
染料相互の配合により染色性の向上等、好結果が
得られる場合がある。
次に、本発明を実施例によつて更に具体的に説
明するが、本発明はその要旨を超えない限り以下
の実施例に限定されるものではない。
実施例 １
で示される化合物38.6ｇを濃塩酸35mlおよび水
300mlを混合した溶液に溶解させ、この溶液を０
〜５℃に氷冷し、亜硝酸ナトリウム11.4ｇを水75
mlに溶解した溶液を滴下した。０〜５℃で２時間
撹拌したのちスルフアミン酸を少量加えてジアゾ
液とした。
一方、３−シアノ−６−ヒドロキシ−４−メチ
ルピリド−２−オン22.5ｇ、酢酸ナトリウム3.1
ｇおよび93重量％水酸化ナトリウム6.3ｇを水
1800mlに溶解し、カツプリング溶液とした。
このカツプリング溶液中に０〜５℃にて、ジア
ゾ液を30分を要して添加し、さらに２時間撹拌し
た。析出した結晶を別した後、水洗および乾燥
を行ない。下記式
で示されるアゾ化合物の黄色結晶54.4ｇを得た。
このアゾ化合物のアセトン中における最大吸収波
長（以後λmaxと略す）は429nｍであつた。
次に、上記アゾ化合物41.8ｇ、炭酸ナトリウム
10.6ｇおよびクロルベンゼン150mlの混合物中に
ジメチル硫酸13.9ｇを、０〜５℃で添加し、同温
度で５時間反応させた。反応後、水蒸気蒸留し
て、クロルベンゼンを留去し、析出した結晶を
別し、水洗後乾燥して下記式
で示される染料の黄色結晶40.2ｇを得た。この染
料の入maxは430nｍであつた。
本実施例で得られたモノアゾ染料0.5ｇをナフ
タレンスルホン酸−ホルムアルデヒド縮合物１ｇ
および高級アルコール硫酸エステル２ｇを含む水
３に分散させて染色浴を調製した。
この染色浴にポリエステル繊維100ｇを浸漬し、
130℃で60分間染色した後、ソーピング、水洗お
よび乾燥を行なつたところ、耐光堅牢度および昇
華堅牢度および水堅牢度にすぐれた鮮明な緑味黄
色の染布が得られた。また、本実施例染料の温度
安定性、PH安定性は良好であつた。
実施例 ２
下記式
で示される化合物30.1ｇを濃塩酸30mlおよび水
200ml中に溶解させて０〜５℃に水冷し、亜硝酸
ナトリウム7.6ｇを水50mlに溶解した溶液を０〜
５℃で滴下した。同温度で２時間撹拌した後、ス
ルフアミン酸を少量加えてジアゾ液とした。一
方、３−シアノ−１，４−ジメチル−６−ヒドロ
キシピリド−２−オン16.4ｇ、酢酸ナトリウム
28.7ｇおよび水酸化ナトリウム4.2ｇを水1200ml
に溶解しカツプリング溶液とした。このカツプリ
ング溶液中に０〜５℃にしてジアゾ液を添加し、
同温度で２時間撹拌した。析出した結晶を別し
た後、水洗および乾燥を行ない
下記式
で示される染料の黄色結晶42.8ｇを得た。
この染料のλmaxは431nｍであつた。
本実施例で得られた染料を用いて、ポリエステ
ル繊維の高温染色（130℃）を行なつたところ、
鮮明な緑味黄色の染布が得られた。得られた染布
の耐光、昇華および堅牢度は良好であつた。ま
た、染色時の温度安定性およびPH安定性は良好で
あつた。
実施例 ３〜21
表−１〜３に記載した染料を使用して、実施例
１と同様の方法でポリエステル繊維を染色した。
各染料のλmaxおよび染布の色調を表−１〜３に
示す。
The present invention relates to a monoazo dye for polyester fibers, and more specifically, it dyes polyester fibers in a vivid greenish-yellow color, has excellent color fastness, particularly light fastness, sublimation fastness, and water fastness, and dyes. This invention relates to monoazo dyes with excellent temperature stability and PH stability. The present invention will be explained in detail below. The monoazo dye of the present invention has the following general formula [] (In the formula, R 1 represents a phenyl group, benzyl group or phenethyl group, R 2 represents a C 1-4 alkyl group,
C 1-4 alkoxycarbonyl C 1-3 alkyl group or
C 1-4 alkoxy C 1-4 group, n is 1 or 2
It is. ) is a monoazo dye for polyester fibers. The monoazo dye represented by the above general formula [] is
For example, (A) general formula [] (In the formula, R 1 and n are the same as the above definition) A compound represented by the general formula [ ] The compound shown or the general formula [] D-SO 2 R 2 ... [] (In the formula, D represents a phenyl group or tolyl group, and R 2 is the same as the above definition.) The compound shown or the general formula [] (R 2 O) 2 SO 2 ... [] (In the formula, R 2 is the same as the above definition) By reacting with a compound represented by (B) general formula [] (In the formula, R 1 and n are the same as defined above.) Diazotizing the aniline by a conventional method,
General formula [] (In the formula, R 2 is the same as defined above.) It is produced by coupling with a pyridone represented by the following formula. According to the method (A) for producing a dye of the present invention, anilines represented by the general formula [] are diazotized by a conventional method, and 3-cyano-6-hydroxy-4-methylpyrid-2-one or an alkali metal salt thereof is The azo compound represented by the general formula [] is obtained by coupling with a conventional method, and then the azo compound obtained is combined with an aromatic compound such as chlorobenzene, dichlorobenzene, nitrobenzene, or o-nitrotoluene, or N such as dimethylformamide. - an organic base such as pyridine, piperidine, triethylamine or sodium carbonate in an inert organic solvent such as an N-alkylpyrrolidone such as alkylformamide or N-methylpyrrolidone, a ketone such as acetone or methyl ethyl ketone, or an alcohol such as methanol or ethanol; potassium carbonate, magnesium oxide,
In the presence of an inorganic base such as sodium hydroxide, a sulfonic acid ester represented by the general formula [], a halide represented by the general formula [], or a sulfuric acid ester represented by the general formula [], and a temperature of -30°C to 100°C.
By the reaction, a pyridone-based azo dye represented by the general formula [] can be obtained with good purity and high yield. Specifically, the anilines represented by the general formula [] used as the diazo component in the dye manufacturing method (B) of the present invention are o-, m-, or p-
(phenoxyethoxycarbonyl)aniline, o-, m-, or p-(phenoxyethoxyethoxycarbonyl)aniline, o-, m-, or p-(benzyloxyethoxycarbonyl)aniline, o-, m- , or p-(benzyloxyethoxyethoxycarbonyl)aniline, o-, m-, or p-(phenethyloxyethoxycarbonyl)aniline, o-, m-, or p-(phenethyloxyethoxyenoxycarbonyl) ) aniline, etc. The pyridones represented by the general formula [ ] used as the coupling component can be obtained, for example, by condensing and cyclizing acetoacetate, cyanoacetate, and an optionally substituted alkylamine. In the latter production method of the present invention, commonly used methods are used for the diazotization and coupling reactions. For example, phenoxyethoxycarbonylanilines are diazotized by adding to nitrosic sulfuric acid prepared from concentrated sulfuric acid and sodium nitrite, or dissolved or suspended in an aqueous hydrochloric acid solution, and then diazotized by adding an aqueous sodium nitrite solution, 3-cyano-4-methyl-6-hydroxy-
This is carried out by adding pyridones to an alkaline aqueous solution such as sodium acetate, sodium carbonate, or sodium hydroxide. Although the coupling reaction can be carried out under neutral or alkaline conditions, it is preferably carried out under slightly acidic conditions. Fibers that can be dyed with the monoazo dye of the present invention include polyester fibers made of polyethylene terephthalate, polycondensates of terephthalic acid and 1,4-bis-(hydroxymethyl)cyclohexane, and natural fibers such as cotton, silk, and wool. Examples include blended products and blended products of fibers and the above-mentioned polyester fibers. In order to dye polyester fibers using the dye of the present invention, since the dye represented by the general formula [] shown above is insoluble or sparingly soluble in water, naphthalene sulfonic acid and formaldehyde are used as dispersants in a conventional method. Dyeing or printing may be carried out by preparing a dyeing bath or printing paste in which a condensate, higher alcohol sulfuric ester, higher alkylbenzene sulfonate or the like is dispersed in an aqueous medium. For example, in the case of dip dyeing, polyester fibers or their blends can be dyed with excellent fastness by applying ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing. In this case, even better results can be obtained if an acidic substance such as formic acid, acetic acid, phosphoric acid or ammonium sulfate is added to the dyeing bath. Furthermore, the dye represented by the general formula [ ] of the present invention may be used in combination with dyes of the same type or dyes of other types, and among these, the dyes represented by the general formula [ ] may be combined to improve dyeability. Good results may be obtained, such as improved performance. Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 Add 38.6g of the compound shown to 35ml of concentrated hydrochloric acid and water.
Dissolve 300ml in the mixed solution, and add this solution to 0.
Cool on ice to ~5℃ and add 11.4g of sodium nitrite to 75% of water.
ml solution was added dropwise. After stirring at 0 to 5°C for 2 hours, a small amount of sulfamic acid was added to obtain a diazo liquid. Meanwhile, 22.5 g of 3-cyano-6-hydroxy-4-methylpyrid-2-one, 3.1 g of sodium acetate
g and 6.3 g of 93 wt% sodium hydroxide in water.
It was dissolved in 1800ml to make a coupling solution. The diazo solution was added to this coupling solution at 0 to 5°C over 30 minutes, and the mixture was further stirred for 2 hours. After separating the precipitated crystals, they were washed with water and dried. The following formula 54.4 g of yellow crystals of an azo compound represented by was obtained.
The maximum absorption wavelength (hereinafter abbreviated as λmax) of this azo compound in acetone was 429 nm. Next, 41.8g of the above azo compound, sodium carbonate
13.9 g of dimethyl sulfate was added to a mixture of 10.6 g of chlorobenzene and 150 ml of chlorobenzene at 0 to 5°C, and the mixture was reacted at the same temperature for 5 hours. After the reaction, chlorobenzene was distilled off by steam distillation, and the precipitated crystals were separated, washed with water, and dried to obtain the following formula. 40.2 g of yellow crystals of the dye represented by were obtained. The maximum penetration of this dye was 430 nm. 0.5g of the monoazo dye obtained in this example was mixed with 1g of naphthalenesulfonic acid-formaldehyde condensate.
A dyeing bath was prepared by dispersing it in water 3 containing 2 g of higher alcohol sulfate. Immerse 100g of polyester fiber in this dyeing bath,
After dyeing at 130°C for 60 minutes, soaping, washing with water, and drying, a bright greenish-yellow dyed fabric with excellent light fastness, sublimation fastness, and water fastness was obtained. Further, the temperature stability and PH stability of the dye of this example were good. Example 2 The following formula Add 30.1g of the compound shown to 30ml of concentrated hydrochloric acid and water.
A solution of 7.6 g of sodium nitrite dissolved in 50 ml of water was dissolved in 200 ml and cooled with water to 0 to 5°C.
It was added dropwise at 5°C. After stirring at the same temperature for 2 hours, a small amount of sulfamic acid was added to form a diazo liquid. Meanwhile, 16.4 g of 3-cyano-1,4-dimethyl-6-hydroxypyrid-2-one, sodium acetate
28.7g and 4.2g of sodium hydroxide in 1200ml of water
A coupling solution was prepared. A diazo solution was added to this coupling solution at 0 to 5°C,
The mixture was stirred at the same temperature for 2 hours. After separating the precipitated crystals, wash with water and dry. 42.8 g of yellow crystals of the dye represented by were obtained. The λmax of this dye was 431 nm. When polyester fiber was dyed at high temperature (130°C) using the dye obtained in this example,
A vivid greenish-yellow dyed fabric was obtained. The dyed fabric obtained had good light fastness, sublimation, and fastness. Furthermore, the temperature stability and PH stability during dyeing were good. Examples 3 to 21 Polyester fibers were dyed in the same manner as in Example 1 using the dyes listed in Tables 1 to 3.
Tables 1 to 3 show the λmax of each dye and the color tone of the dyed fabric.
【表】【table】
【表】【table】
【表】【table】
Claims (1)
エネチル基を表わし、R2はC1〜4アルキル基、
C1〜4アルコキシカルボニルC1〜3アルキル基または
C1〜4アルコキシC1〜4アルキル基を表わし、ｎは１
または２である。） で示されるポリエステル系繊維用モノアゾ染料。[Claims] 1. The following general formula (In the formula, R 1 represents a phenyl group, benzyl group or phenethyl group, R 2 represents a C 1-4 alkyl group,
C 1-4 alkoxycarbonyl C 1-3 alkyl group or
C 1-4 alkoxy represents a C 1-4 alkyl group, and n is 1
Or 2. ) Monoazo dye for polyester fibers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1726682A JPS58136656A (en) | 1982-02-05 | 1982-02-05 | Monoazo dye for polyester fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1726682A JPS58136656A (en) | 1982-02-05 | 1982-02-05 | Monoazo dye for polyester fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58136656A JPS58136656A (en) | 1983-08-13 |
| JPH0358387B2 true JPH0358387B2 (en) | 1991-09-05 |
Family
ID=11939159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1726682A Granted JPS58136656A (en) | 1982-02-05 | 1982-02-05 | Monoazo dye for polyester fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58136656A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3736817A1 (en) * | 1987-10-30 | 1989-05-11 | Basf Ag | PYRIDONAZO DYES AND THEIR USE |
| KR19980072440A (en) * | 1997-03-05 | 1998-11-05 | 성재갑 | Mono-Azo Disperse Dyes for Polyester Fibers |
-
1982
- 1982-02-05 JP JP1726682A patent/JPS58136656A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58136656A (en) | 1983-08-13 |
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