JPH07252425A - Monoazo dye - Google Patents
Monoazo dyeInfo
- Publication number
- JPH07252425A JPH07252425A JP6913994A JP6913994A JPH07252425A JP H07252425 A JPH07252425 A JP H07252425A JP 6913994 A JP6913994 A JP 6913994A JP 6913994 A JP6913994 A JP 6913994A JP H07252425 A JPH07252425 A JP H07252425A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- dyeing
- dye
- fibers
- fastness
- 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.)
- Pending
Links
- 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 title claims abstract description 13
- 239000000835 fiber Substances 0.000 claims abstract description 20
- 238000004043 dyeing Methods 0.000 claims abstract description 16
- 229920001410 Microfiber Polymers 0.000 claims abstract description 13
- 229920000728 polyester Polymers 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000005406 washing Methods 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000007796 conventional method Methods 0.000 abstract description 3
- 230000008878 coupling Effects 0.000 abstract description 2
- 238000010168 coupling process Methods 0.000 abstract description 2
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 26
- 239000004744 fabric Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 polyethylene terephthalate Polymers 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 239000003513 alkali Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 239000003658 microfiber Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- JOZDUGKPSFOQKJ-UHFFFAOYSA-N 2-[n-(2-benzoyloxyethyl)anilino]ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN(C=1C=CC=CC=1)CCOC(=O)C1=CC=CC=C1 JOZDUGKPSFOQKJ-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002657 fibrous material Substances 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
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はポリエステル繊維に有用
なモノアゾ染料に関する。本発明は特にポリエステル系
ファインデニール繊維を洗濯堅牢度と耐光堅牢度に優れ
た水不溶性の橙色系モノアゾ分散染料に関する。FIELD OF THE INVENTION This invention relates to monoazo dyes useful in polyester fibers. The present invention particularly relates to a water-insoluble orange monoazo disperse dye which is excellent in fastness to washing and light fastness of polyester fine denier fiber.
【０００２】[0002]
【従来の技術】近年の合成繊維の発展は目覚しく、特に
ポリエステル繊維は種々の異形断面糸や異収縮糸、更に
極細繊維など多くの新しい製品が生み出され、新しい機
能性繊維材料を創り出している。例えば、優れた風合を
出すための素材として極細繊維が製造され、０．３デニ
ール以下の超極細繊維（ウルトラマイクロファイバー）
も大量に生産されている。しかしこれらの極細繊維は従
来の染料での染色は難しく、特に洗濯堅牢度等の湿潤堅
牢度の良好な染色が得られないという問題が生じてい
る。2. Description of the Related Art In recent years, the development of synthetic fibers has been remarkable, and in particular, polyester fibers have produced many new products such as various modified cross-section yarns, different contraction yarns, and ultrafine fibers, and have created new functional fiber materials. For example, ultrafine fibers are produced as a material for producing excellent texture, and ultrafine fibers of 0.3 denier or less (ultramicrofiber)
Are also produced in large quantities. However, it is difficult to dye these ultrafine fibers with a conventional dye, and there is a problem that dyeing with good wet fastness such as fastness to washing cannot be obtained.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、良好な洗濯
堅牢度を有し、しかもアルカリ汗堅牢度及び耐光堅牢度
を備えた橙色分散染料を提供することを目的とするもの
である。SUMMARY OF THE INVENTION It is an object of the present invention to provide an orange disperse dye having good wash fastness, alkaline sweat fastness and light fastness.
【０００４】[0004]
【課題を解決するための手段】本発明は、下記一般式
〔Ｉ〕The present invention has the following general formula [I]:
【０００５】[0005]
【化３】 [Chemical 3]
【０００６】（式中、Ｘは塩素原子又は臭素原子を表わ
し、Ｙは水素原子、ハロゲン原子又はメチル基を表わ
し、Ｒはフェニル基、フェノキシ基又はベンジル基を表
わす。）で示されるモノアゾ染料を要旨とするものであ
る。上記染料の中でも下記の構造式〔II〕で示される染
料が、特に好ましい。(Wherein X represents a chlorine atom or a bromine atom, Y represents a hydrogen atom, a halogen atom or a methyl group, and R represents a phenyl group, a phenoxy group or a benzyl group). It is a summary. Among the above dyes, the dye represented by the following structural formula [II] is particularly preferable.
【０００７】[0007]
【化４】 [Chemical 4]
【０００８】前記一般式〔Ｉ〕で示されるモノアゾ染料
は、例えば、下記一般式〔III 〕The monoazo dye represented by the general formula [I] is, for example, the following general formula [III]
【０００９】[0009]
【化５】 [Chemical 5]
【００１０】（式中、Ｘは前記と同様の意義を有す
る。）で示されるアミン類を常法に従ってジアゾ化し、
次いで下記一般式〔IV〕(Wherein X has the same meaning as above), the amines are diazotized by a conventional method,
Then the following general formula [IV]
【００１１】[0011]
【化６】 [Chemical 6]
【００１２】（式中、Ｙ及びＲは前記と同様の意義を有
する。）にて示されるアニリン類とカップリングするこ
とにより製造することができる。本発明のモノアゾ染料
により染色し得る繊維類としてはポリエチレンテレフタ
レート、ポリブ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、更にナイロ
ン等の合成繊維あるいは木綿、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、混織品などの混合
繊維製品が挙げられる。又ポリエステル繊維としては通
常の太さの繊維（レギュラーデニール繊維）から１デニ
ール以下の極細繊維（ファインデニール繊維）までが対
象として挙げられる。特に本発明の染料によれば、一般
に染色の困難な極細繊維、その中の０．３デニール以下
の超極細繊維（ウルトラマイクロファイバー）まで良好
に染色できる点特筆される。(Wherein Y and R have the same meanings as described above), and can be produced by coupling with an aniline. Fibers that can be dyed with the monoazo dye of the present invention include polyethylene terephthalate, polybutylene terephthalate, polyester fibers composed of a polycondensation product of terephthalic acid and 1,4-bis- (hydroxymethyl) cyclohexane, and nylon and the like. Examples of the mixed fiber product include a fiber, a natural fiber such as cotton, silk, and wool, and a blended product of the above polyester fiber and a blended woven product. Examples of the polyester fibers include fibers having a normal thickness (regular denier fibers) to ultrafine fibers having a denier of 1 denier or less (fine denier fibers). In particular, the dye of the present invention is particularly advantageous in that it is possible to satisfactorily dye even ultrafine fibers that are generally difficult to dye, and ultrafine fibers (ultramicrofibers) having a denier of 0.3 denier or less.
【００１３】本発明の染料を用いて染色を実施するにあ
たっては、常法により、分散剤を使用し、前記一般式
〔Ｉ〕で示されるモノアゾ染料を水性媒体中に分散させ
て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、浸染を行なう場合には、高温染色
法、キャリヤー染色法、サーモゾル染色法などの通常の
染色処理法を適用することにより、ポリエステル繊維な
いしはその混紡品、混織品に堅牢度のすぐれた染色を施
すことができる。また、場合により、染色浴に酸性物質
を添加しておくことにより、さらに好結果が得られるこ
とがある。In carrying out dyeing with the dye of the present invention, a monoazo dye represented by the general formula [I] is dispersed in an aqueous medium by a conventional method using a dispersant, and a dye bath or printing is conducted. A paste may be prepared, and dyeing or printing may be performed. For example, in the case of dyeing, by applying a normal dyeing treatment method such as a high temperature dyeing method, a carrier dyeing method and a thermosol dyeing method, it is possible to dye polyester fibers or their blended fabrics and blended fabrics with excellent fastness. Can be given. Further, depending on the case, better results may be obtained by adding an acidic substance to the dyeing bath.
【００１４】本発明のモノアゾ染料を用いて上記の浸染
または捺染により得られた染布は、洗濯堅牢度に優れ、
また、耐アルカリ汗堅牢度、耐光堅牢度、耐昇華堅牢度
及び耐水堅牢度等の諸堅牢度に優れたものである。更
に、この染布に後加工を施した場合でも、本発明では湿
潤堅牢度が大幅に低下すると言うことはない。なお、本
発明のモノアゾ染料は同系統の染料あるいは他系統の染
料と併用してもよい。The dyed cloth obtained by the above dyeing or printing using the monoazo dye of the present invention has excellent fastness to washing,
Further, it is excellent in various fastnesses such as alkali sweat fastness, light fastness, sublimation fastness and water fastness. Further, even when the dyed cloth is post-processed, the wet fastness is not significantly lowered in the present invention. The monoazo dye of the present invention may be used in combination with a dye of the same system or a dye of another system.
【００１５】[0015]
【実施例】次に、本発明を実施例により更に具体的に説
明するが、本発明は、その要旨を越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 前記一般式〔Ｉ〕に於てＸが塩素原子、Ｙが水素原子、
Ｒがフェニル基である下記構造式〔II〕EXAMPLES Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples unless it exceeds the gist. Example 1 In the general formula [I], X is a chlorine atom, Y is a hydrogen atom,
The following structural formula [II] in which R is a phenyl group
【００１６】[0016]
【化７】 [Chemical 7]
【００１７】のモノアゾ染料０．０２５ｇをナフタレン
スルホン酸−ホルムアルデヒド縮合物０．０２５ｇおよ
び高級アルコール硫酸エステル０．０２５ｇを含む水２
００ｍｌ中に分散させ染色浴を調製した。この染色浴に
繊径が２デニールと０．０１デニールのポリエステル繊
維の交織布１０ｇを浸漬し、１３５℃で３０分間染色し
た後、ソーピング、水洗および乾燥を行なったところ、
橙色の染布が得られた。なお、上記の染料にて染色され
た上記、交織布の洗濯堅牢度は４−５級と優れたもので
あった。Water 2 containing 0.025 g of monoazo dye of 0.025 g of naphthalenesulfonic acid-formaldehyde condensate and 0.025 g of higher alcohol sulfate ester.
It was dispersed in 00 ml to prepare a dye bath. In this dyeing bath, 10 g of a mixed woven fabric of polyester fibers having diameters of 2 denier and 0.01 denier was dipped, dyed at 135 ° C. for 30 minutes, and then soaped, washed with water and dried.
An orange dyed fabric was obtained. The washing fastness of the above-mentioned interwoven fabric dyed with the above dye was excellent at 4-5 grade.
【００１８】尚、洗濯堅牢度はＪＩＳ Ｌ０８４８ Ａ
法でのナイロン白布の汚染度を判定した。尚、本実験例
で使用した染料は以下のようにして製造した。２，６−
ジクロロ−４−ニトロアニリン４．２ｇを９８％硫酸２
０ｇ中に３０℃で溶解させ、次いで４３％ニトロシル硫
酸６．５ｇを３０℃で加えた後、２時間攪拌し、ジアゾ
液を得た。次いで、Ｎ，Ｎ−ビス（フェニルカルボニル
オキシエチル）アニリン７．２ｇをメタノール１５０ｍ
ｌ中溶解した後、前記ジアゾ液を０〜５℃で滴下し、２
時間撹拌した後、濾別し、水で洗浄した後乾燥し、目的
の染料を得た。該染料の最大吸収波長（λmax ：アセト
ン中）は４２４ｎｍであった。The washing fastness is JIS L0848 A.
The degree of staining of nylon white cloth by the method was determined. The dye used in this experimental example was manufactured as follows. 2,6-
Dichloro-4-nitroaniline 4.2 g was added to 98% sulfuric acid 2
It was dissolved in 0 g at 30 ° C., then 6.5 g of 43% nitrosyl sulfuric acid was added at 30 ° C., and the mixture was stirred for 2 hours to obtain a diazo liquid. Then, 7.2 g of N, N-bis (phenylcarbonyloxyethyl) aniline was added to 150 m of methanol.
After dissolving in 1 l, the diazo solution was added dropwise at 0-5 ° C.,
After stirring for an hour, it was filtered off, washed with water and dried to give the desired dye. The maximum absorption wavelength (λ max : in acetone) of the dye was 424 nm.
【００１９】比較例１ 前記一般式〔Ｉ〕と同一の基本骨格を有し、但し、Ｘが
水素原子、Ｙが塩素原子、Ｒがフェニル基である化合物
（特開昭５８−１６０３５５号公報実施例４に記載）を
実施例１に準じて合成し、実施例１と同様にしてマイク
ロファイバー交織布を染色し、評価したところ、洗濯堅
牢度は３−４級、耐光堅牢度は４級と劣るものであっ
た。Comparative Example 1 A compound having the same basic skeleton as that of the above-mentioned general formula [I] except that X is a hydrogen atom, Y is a chlorine atom, and R is a phenyl group (JP-A-58-160355). (Described in Example 4) was synthesized according to Example 1, and the microfiber interwoven cloth was dyed and evaluated in the same manner as in Example 1. The washing fastness was 3-4 grade, and the light fastness was 4 grade. It was inferior.
【００２０】実施例２〜１５ 実施例１に準じて表−１に記載の各染料を合成し、実施
例１と同様にしてマイクロファイバー交織布を染色し、
洗濯堅牢度を調べた。結果を表−１に示す。Examples 2 to 15 The dyes shown in Table 1 were synthesized according to Example 1, and the microfiber interwoven fabric was dyed in the same manner as in Example 1,
The fastness to washing was examined. The results are shown in Table-1.
【００２１】[0021]
【表１】 [Table 1]
【００２２】[0022]
【表２】 [Table 2]
【００２３】[0023]
【発明の効果】本発明の染料を用いれば、ポリエステル
繊維を諸堅牢度、とりわけ洗濯堅牢度、アルカリ汗堅牢
度及び耐光堅牢度に優れた橙色に染色することができ、
特に超極細繊維までも通常の繊度の繊維と同じように良
好に染色することができる。When the dye of the present invention is used, polyester fibers can be dyed in orange color excellent in various fastnesses, particularly fastness to washing, fastness to alkali sweat and fastness to light,
In particular, even ultrafine fibers can be dyed satisfactorily in the same manner as fibers of ordinary fineness.
Claims (4)
原子、ハロゲン原子又はメチル基を表わし、Ｒはフェニ
ル基、フェノキシ基又はベンジル基を表わす。）で示さ
れるモノアゾ染料。1. The following general formula [I]: (In the formula, X represents a chlorine atom or a bromine atom, Y represents a hydrogen atom, a halogen atom or a methyl group, and R represents a phenyl group, a phenoxy group or a benzyl group.).
いるポリエステル繊維の染色法。3. A method for dyeing polyester fibers, which uses the monoazo dye according to claim 1 or 2.
求項３の染色法。4. The dyeing method according to claim 3, wherein the polyester fibers are ultrafine fibers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6913994A JPH07252425A (en) | 1994-03-14 | 1994-03-14 | Monoazo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6913994A JPH07252425A (en) | 1994-03-14 | 1994-03-14 | Monoazo dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07252425A true JPH07252425A (en) | 1995-10-03 |
Family
ID=13394024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6913994A Pending JPH07252425A (en) | 1994-03-14 | 1994-03-14 | Monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07252425A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010024441A1 (en) | 2008-09-01 | 2010-03-04 | 富士フイルム株式会社 | Ultraviolet absorbing agent composition |
-
1994
- 1994-03-14 JP JP6913994A patent/JPH07252425A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010024441A1 (en) | 2008-09-01 | 2010-03-04 | 富士フイルム株式会社 | Ultraviolet absorbing agent composition |
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