JPS6312904B2 - - Google Patents
Info
- Publication number
- JPS6312904B2 JPS6312904B2 JP2019580A JP2019580A JPS6312904B2 JP S6312904 B2 JPS6312904 B2 JP S6312904B2 JP 2019580 A JP2019580 A JP 2019580A JP 2019580 A JP2019580 A JP 2019580A JP S6312904 B2 JPS6312904 B2 JP S6312904B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- water
- dye
- parts
- 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
Links
- 239000000835 fiber Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 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 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 210000002268 wool Anatomy 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- 229920002978 Vinylon Polymers 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- FJSKSYVNULWVAZ-XTQSDGFTSA-N Jubanine B Chemical compound O=C1N\C=C\C(=C2)C(OC)=CC=C2OC2CCN(C(=O)C(CC=3C=CC=CC=3)NC(=O)C(CC=3C=CC=CC=3)N(C)C)C2C(=O)NC1CC1=CC=CC=C1 FJSKSYVNULWVAZ-XTQSDGFTSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JMZFEHDNIAQMNB-UHFFFAOYSA-N m-aminophenylboronic acid Chemical compound NC1=CC=CC(B(O)O)=C1 JMZFEHDNIAQMNB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明はヒドロキシル基含有繊維、窒素含有繊
維またはこれらの混合繊維を、堅牢な赤色に染色
する新規なホウ酸含有モノアゾ色素に関するもの
である。
以下に本発明を詳細に説明する。
本発明に係る色素は下記一般式〔〕
〔式中、Ｋは
The present invention relates to a novel boric acid-containing monoazo dye that dyes hydroxyl group-containing fibers, nitrogen-containing fibers, or mixed fibers thereof in a strong red color. The present invention will be explained in detail below. The dye according to the present invention has the following general formula [] [In the formula, K is
【式】また は[Formula] Also teeth
【式】を表わす。ただ
し、R1は水素原子、アセチル基またはベンゾイ
ル基を表わし、R2は水素原子、メチル基または
エチル基を表わし、R3は水素原子、アセチル基
またはベンゾイル基を表わす。〕で示される水可
溶性のホウ酸含有モノアゾ色素である。
前示一般式〔〕で示される色素は、たとえば
下記構造式〔〕
のジアゾニウム塩を、下記一般式〔〕Represents [formula]. However, R 1 represents a hydrogen atom, an acetyl group or a benzoyl group, R 2 represents a hydrogen atom, a methyl group or an ethyl group, and R 3 represents a hydrogen atom, an acetyl group or a benzoyl group. ] is a water-soluble boric acid-containing monoazo dye. For example, the dye represented by the general formula [] shown below has the following structural formula [] The diazonium salt of is expressed by the following general formula []
【式】または[expression] or
【式】
〔式中、R1、R2及びR3は前記定義に同じ〕で示
される化合物とカツプリングさせることにより製
造することができる。
本発明の色素により染色されるヒドロキシル基
含有繊維としてはビニロン、木綿等があげられ、
窒素含有繊維としては、羊毛、絹、合成ポリアミ
ドおよびポリウレタン等があげられる。更にこれ
らの混紡品または混織品も本発明の色素により染
色しうる。
本発明の色素により前記繊維を染色するにあた
つては、公知の浸染染色法、パデイング染色法、
捺染染色法が適用される。また、本発明の色素
は、特に絹の浸染染色法において、従来の酸性染
料とは異つて、PHが中性領域でも良好な染着性を
示す。
以下に本発明を実施例によりさらに具体的説明
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。
尚、実施例中「部」とあるのは「重量部」を示
す。
実施例 １
下記構造式
で示されるモノアゾ染料0.1部、水100部からなる
染色浴を調製し、酢酸にてPH6.5とした。次にウ
ールモスリン４ｇを上記染色浴で92〜95℃×45分
処理した。処理後、冷水で充分水洗したところ、
ウールは鮮明な青味赤色に染色されていた。
更にビニロン繊維およびナイロン タフタ（帝
人(株)製）についても同様な処理を実施したとこ
ろ、各繊維は鮮明な青味赤色に染色されていた。
上記３種の染色布をJIS Ｌ−0844 Ｂ−１法に
準じて洗濯試験を行なつた結果、良好な耐洗濯堅
牢性を有していた。
本実施例で使用した染料は、ｍ−アミノフエニ
ルボロン酸を常法に従つて−5゜〜−10℃でジアゾ
化し、これをＮ−ベンゾイルＨ酸を希アルカリ水
に溶解した溶液へPH10付近に保ちながら注加する
ことによりカツプリングさせて製造した。
本品のλmax（水）は509nｍ、であつた。
実施例 ２
下記構造式
で示されるモノアゾ染料10部、チオジエチレング
リコール40部、尿素30部、水310部、酒石酸アン
モニウム５部並びに水、ミネラルターペンおよび
乳化剤より調整されたｏ／ｗ型エマルジヨン605
部からなる捺染色糊を調製した。
次にオートスクリーン捺染機を用い、ナイロン
タフタ（帝人(株)製）に印捺、80℃×３分で中間
乾燥し、102℃×30分スチーミング処理をした。
その後、水洗し、２ｇ／Ｌの非イオン界面活性
剤を含むソーピング浴で50℃×10分ソーピング
し、更に水洗、乾燥して鮮明な青味赤色の捺染物
を得た。また羊毛、ポリウレタン繊維、絹につい
ても同様な操作により鮮明な青味赤色の捺染物を
得た。
本実施例で使用した染料は実施例１に記載の方
法に準じて合成した。
本品のλmax（水）509であつた。
実施例 ３
表−１に示す染料を使用して、実施例１に記載
の方法に準じてウールモスリンを染色した。
その結果、表−１に示す色相の染色物が得らIt can be produced by coupling with a compound represented by the formula: [In the formula, R 1 , R 2 and R 3 are the same as defined above]. Hydroxyl group-containing fibers that can be dyed with the dye of the present invention include vinylon, cotton, etc.
Examples of nitrogen-containing fibers include wool, silk, synthetic polyamides, and polyurethanes. Furthermore, these blended fabrics or blended fabrics can also be dyed with the dyes of the present invention. When dyeing the fibers with the dye of the present invention, known dyeing methods, padding dyeing methods,
Textile dyeing method is applied. Further, the dye of the present invention exhibits good dyeability even in the neutral pH range, unlike conventional acid dyes, especially in silk immersion dyeing methods. EXAMPLES The present invention will be explained in more detail by examples below, but the present invention is not limited to the following examples unless it exceeds the gist thereof. In addition, "parts" in the examples indicate "parts by weight." Example 1 Structural formula below A dyeing bath consisting of 0.1 part of the monoazo dye shown by and 100 parts of water was prepared, and the pH was adjusted to 6.5 with acetic acid. Next, 4 g of wool muslin was treated in the above dyeing bath at 92 to 95° C. for 45 minutes. After treatment, I rinsed it thoroughly with cold water.
The wool was dyed a bright bluish red. Furthermore, when vinylon fibers and nylon taffeta (manufactured by Teijin Ltd.) were subjected to similar treatments, each fiber was dyed in a vivid bluish red color. The three types of dyed fabrics mentioned above were subjected to a washing test according to the JIS L-0844 B-1 method, and the results showed that they had good washing fastness. The dye used in this example was prepared by diazotizing m-aminophenylboronic acid at -5° to -10°C according to a conventional method, and adding this to a solution of N-benzoyl H acid dissolved in dilute alkaline water at pH 10. It was manufactured by coupling by pouring the liquid while keeping it close to each other. The λmax (water) of this product was 509 nm. Example 2 Structural formula below O/W emulsion 605 prepared from 10 parts of a monoazo dye represented by, 40 parts of thiodiethylene glycol, 30 parts of urea, 310 parts of water, 5 parts of ammonium tartrate, water, mineral turpentine, and an emulsifier.
A printing dyeing paste consisting of parts was prepared. Next, using an autoscreen printing machine, printing was performed on nylon taffeta (manufactured by Teijin Ltd.), intermediate drying was performed at 80°C for 3 minutes, and steaming treatment was performed at 102°C for 30 minutes. Thereafter, it was washed with water, soaped in a soaping bath containing 2 g/L of nonionic surfactant at 50°C for 10 minutes, further washed with water, and dried to obtain a clear bluish-red print. In addition, similar operations were performed on wool, polyurethane fiber, and silk to obtain vivid bluish-red prints. The dye used in this example was synthesized according to the method described in Example 1. The λmax (water) of this product was 509. Example 3 Wool muslin was dyed according to the method described in Example 1 using the dyes shown in Table-1. As a result, dyed products with the hues shown in Table 1 were obtained.
【表】【table】
Claims (1)
を表わし、R2は水素原子、メチル基またはエチ
ル基を表わしR3は水素原子、アセチル基または
ベンゾイル基を表わす。〕で示されるヒドロキシ
ル基含有または窒素含有繊維用モノアゾ色素。[Claims] 1. General formula [In the formula, K represents [formula] or [formula]. However, R 1 represents a hydrogen atom, an acetyl group or a benzoyl group, R 2 represents a hydrogen atom, a methyl group or an ethyl group, and R 3 represents a hydrogen atom, an acetyl group or a benzoyl group. ] A monoazo dye for hydroxyl group-containing or nitrogen-containing fibers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019580A JPS56116754A (en) | 1980-02-20 | 1980-02-20 | Borate group-containing monoazo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019580A JPS56116754A (en) | 1980-02-20 | 1980-02-20 | Borate group-containing monoazo dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56116754A JPS56116754A (en) | 1981-09-12 |
| JPS6312904B2 true JPS6312904B2 (en) | 1988-03-23 |
Family
ID=12020381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019580A Granted JPS56116754A (en) | 1980-02-20 | 1980-02-20 | Borate group-containing monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56116754A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512246A (en) * | 1989-09-21 | 1996-04-30 | Anthony P. Russell | Method and means for detecting polyhydroxyl compounds |
| EP0447196A1 (en) * | 1990-03-16 | 1991-09-18 | Hewlett-Packard Company | Boronic acid dyes |
| EP2120680A2 (en) | 2007-02-06 | 2009-11-25 | Glumetrics, Inc. | Optical systems and methods for rationmetric measurement of blood glucose concentration |
-
1980
- 1980-02-20 JP JP2019580A patent/JPS56116754A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56116754A (en) | 1981-09-12 |
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