JPS63182485A - Enhancement of dyeing fastness - Google Patents
Enhancement of dyeing fastnessInfo
- Publication number
- JPS63182485A JPS63182485A JP62011021A JP1102187A JPS63182485A JP S63182485 A JPS63182485 A JP S63182485A JP 62011021 A JP62011021 A JP 62011021A JP 1102187 A JP1102187 A JP 1102187A JP S63182485 A JPS63182485 A JP S63182485A
- Authority
- JP
- Japan
- Prior art keywords
- fastness
- allylamine
- formula
- dyed
- group
- 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
- 238000004043 dyeing Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 29
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical class NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 11
- 229920003043 Cellulose fiber Polymers 0.000 claims description 6
- 239000000985 reactive dye Substances 0.000 claims description 6
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical group C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- -1 hydroxyethyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 23
- 238000002845 discoloration Methods 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- 238000012545 processing Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- JDCBWJCUHSVVMN-SCSAIBSYSA-N (2r)-but-3-en-2-amine Chemical compound C[C@@H](N)C=C JDCBWJCUHSVVMN-SCSAIBSYSA-N 0.000 description 13
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 238000005562 fading Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- QVHJUWAWVKJYTO-UHFFFAOYSA-N methyl(prop-2-enyl)azanium;chloride Chemical compound Cl.CNCC=C QVHJUWAWVKJYTO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- WGESLFUSXZBFQF-UHFFFAOYSA-N n-methyl-n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCN(C)CC=C WGESLFUSXZBFQF-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000007796 conventional method Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000982 direct dye Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- XCENPWBBAXQVCG-UHFFFAOYSA-N 4-phenylpiperidine-4-carbaldehyde Chemical compound C=1C=CC=CC=1C1(C=O)CCNCC1 XCENPWBBAXQVCG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、染色物の染色堅牢度向上方法に関する。更に
詳しくは、本発明は、セルロース系繊維又はセルロース
系繊維と他の繊維からなる繊維材料の反応染料又は直接
染料による染色物を後処理して、湿潤堅牢度、耐光堅牢
度、耐塩素堅牢度等の染色堅牢度を向上させると同時に
樹脂加工、熱処理等による変色の非常に少ない方法に関
する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a method for improving the color fastness of dyed products. More specifically, the present invention provides post-treatment of dyed products of cellulose fibers or textile materials made of cellulose fibers and other fibers using reactive dyes or direct dyes to improve wet fastness, light fastness, and chlorine fastness. This invention relates to a method that improves the color fastness of products such as the like, while at the same time causing very little discoloration due to resin processing, heat treatment, etc.
従来技術及びその問題点
反応染料は、その色彩が鮮明で湿潤堅牢度が優れている
ため、直接染料等に代り多く用いられるようになってき
た。しかしながら、反応染料は繊維と共何結合を形成し
、強固に結合するが、それでも湿潤堅牢度、耐塩素堅牢
度がなお不十分である。Prior art and its problems Reactive dyes have come to be used in place of direct dyes because of their vivid colors and excellent wet fastness. However, although reactive dyes form covalent bonds with fibers and are strongly bonded, wet fastness and chlorine fastness are still insufficient.
この問題に対する対策として染色物を染料固着剤と呼ば
れるカチオン性ポリマーの希薄水溶液で処理することが
実施されている。As a countermeasure to this problem, dyed products are treated with a dilute aqueous solution of a cationic polymer called a dye fixing agent.
最近、上記処理方法として、第１級アリルアミンやＮ−
置換第２級アリルアミンの単独重合物で処理する方法、
Ｎ−置換第２級アリルアミンと第１級アリルアミン、第
２級ジアリルアミン又はＮ。Recently, primary allylamine and N-
A method of treating with a homopolymer of substituted secondary allylamine,
N-substituted secondary allylamine and primary allylamine, secondary diallylamine or N.
Ｎ−ジ置換ジアリル第４級アンモニウム塩との共重合物
で処理する方法（特開昭６１−２３１２８３号）が提案
されている。しかしながら、これらの方法には、染色堅
牢度が不充分であったり、樹脂加工、熱処理等による変
色即ち色相の変化や捺染物の白湯の黄変等が著しかった
りする問題点がある。A method of treating with a copolymer with an N-disubstituted diallyl quaternary ammonium salt (Japanese Patent Application Laid-open No. 231283/1983) has been proposed. However, these methods have problems such as insufficient color fastness, discoloration (change in hue) due to resin processing, heat treatment, etc., and significant yellowing of the hot water of the printed material.
問題点を解決するための手段
本発明者は上記問題点に鑑み、鋭意研究を重ねた結果、
従来この種の処理に用いられたことのない特定のＮ−置
換第２級アリルアミン誘導体とＮ−置換第３級ジアリル
アミン誘導体との共重合物を用いて後処理するときには
、湿潤堅牢度、耐光堅牢度、耐塩素堅牢度等の染色堅牢
度が顕著に向上すると共に、樹脂加工、熱処理等による
変色が非常に少ないことを見出し、本発明を完成した。Means for Solving the Problems In view of the above-mentioned problems, the inventor has conducted extensive research and has found that:
When post-processing is performed using a copolymer of a specific N-substituted secondary allylamine derivative and an N-substituted tertiary diallylamine derivative, which has never been used in this type of treatment, wet fastness and light fastness are The present invention has been completed based on the discovery that color fastness such as color fastness and chlorine resistance are significantly improved, and discoloration due to resin processing, heat treatment, etc. is extremely small.
即ち、本発明は、セルロース系繊維又はセルロース系繊
維と他の繊維からなる繊維材料の反応染料による染色物
を、下記［Ｉ］で表わされるモノマーと下記［Ｉ［］で
表わされるモノマーとをモル比１：９〜９：１の割合で
共重合させて得た共重合物で後処理することを特徴とす
る染色物の染色堅牢度向上方法に係る。That is, the present invention dyes cellulose fibers or fiber materials consisting of cellulose fibers and other fibers with reactive dyes by mixing monomers represented by [I] below and monomers represented by [I[] below in molar proportions. The present invention relates to a method for improving color fastness of a dyed article, which comprises post-treating with a copolymer obtained by copolymerizing at a ratio of 1:9 to 9:1.
［Ｉ］式 ［式中、Ｒ１は水素原子又はメチル基を示す。[I] Formula [In the formula, R1 represents a hydrogen atom or a methyl group.
Ｒ２はＣ，〜Ｃ６のアルキル基、ベンジル基、ヒドロキ
シエチル基又はシクロアルキル基を示す。ＨＸは無機酸
又は有機酸を示す。］で表わされるＮ−置換第２級アリ
ルアミン誘導体。R2 represents a C, to C6 alkyl group, benzyl group, hydroxyethyl group or cycloalkyl group. HX represents an inorganic acid or an organic acid. ] N-substituted secondary allylamine derivative.
［ＩＩ１式
［式中、Ｒ３及びＲ４は同−又は相異なって水素原子又
はメチル基を示す。Ｒ２及びＨＸは前記に同じ。］で表
わされるＮ−置換第３級ジアリルアミン誘導体。[Formula II1 [In the formula, R3 and R4 are the same or different and represent a hydrogen atom or a methyl group. R2 and HX are the same as above. ] N-substituted tertiary diallylamine derivative.
本発明では［Ｉ］のモノマーと［ＩＩ］のモノマーとの
共重合物を用いることを必須とし、これにより樹脂加工
、熱処理等による変色が非常に少なく、その上で染色物
の湿潤堅牢度、耐光堅牢度、耐塩素堅牢度等の染色堅牢
度を同時に且つ高水準で満足できる。一方、［Ｉ］又は
［ＩＩ］のモノマーの単独重合物で染色物を処理した場
合では充分な結果は得られない。即ち［Ｉ］のモノマー
の単独重合物では、樹脂加工、熱処理等による変色が激
しく、又湿潤堅牢度の向上も充分ではない。In the present invention, it is essential to use a copolymer of the monomer [I] and the monomer [II], which causes very little discoloration due to resin processing, heat treatment, etc., and also improves the wet fastness of the dyed product. It can simultaneously satisfy high levels of color fastness such as light fastness and chlorine fastness. On the other hand, when a dyed article is treated with a homopolymer of the monomer [I] or [II], satisfactory results cannot be obtained. That is, the homopolymer of the monomer [I] undergoes severe discoloration due to resin processing, heat treatment, etc., and also does not sufficiently improve wet fastness.
［■］のモノマーの単独重合物では耐塩素堅牢度が向上
せず不満足である。The homopolymer of the monomer [■] does not improve the fastness to chlorine and is unsatisfactory.
本発明において式［Ｉ］のＮ−置換第２級アリルアミン
誘導体は、Ｎに置換基Ｒ２と（メタ）アリル基とを有す
る第２級アミンと酸との塩で、当該第２級アミンとして
は、例えばＮ−メチル（メタ）アリルアミン、Ｎ−エチ
ル（メタ）アリルアミン、Ｎ−プロピル（メタ）アリル
アミン、Ｎ−ブチル（メタ）アリルアミン、Ｎ−アミル
（メタ）アリルアミン、Ｎ−ヒドロキシエチル（メタ）
アリルアミン、Ｎ−ベンジル（メタ）アリルアミン、Ｎ
−シクロヘキシル（メタ）アリルアミン等があげられる
。又、無機酸としては塩酸、硫酸、燐酸及び硝酸があげ
られる。有機酸の中で好ましいものとしては、酢酸及び
プロピオン酸等の炭素数１〜４の飽和脂肪酸、マレイン
酸、フタル酸及びリンゴ酸等のジカルボン酸等を例示で
きる。In the present invention, the N-substituted secondary allylamine derivative of formula [I] is a salt of a secondary amine having a substituent R2 and a (meth)allyl group on N and an acid, and the secondary amine is , such as N-methyl(meth)allylamine, N-ethyl(meth)allylamine, N-propyl(meth)allylamine, N-butyl(meth)allylamine, N-amyl(meth)allylamine, N-hydroxyethyl(meth)allylamine
Allylamine, N-benzyl(meth)allylamine, N
-cyclohexyl (meth)allylamine and the like. Examples of inorganic acids include hydrochloric acid, sulfuric acid, phosphoric acid and nitric acid. Preferred organic acids include saturated fatty acids having 1 to 4 carbon atoms, such as acetic acid and propionic acid, and dicarboxylic acids, such as maleic acid, phthalic acid, and malic acid.
式［１］のＮ−置換第３級ジアリルアミン誘導体は、Ｎ
に置換基Ｒ２と２個の（メタ）アリル基とを有する第３
級アミンと酸との塩で、当該第３級アミンとしては、例
えばＮ−メチルジ（メタ）アリルアミン、Ｎ−エチルジ
（メタ）アミルアミン、Ｎ−プロビルジ（メタ）アリル
アミン、Ｎ−ブチルジ（メタ）アリルアミン、Ｎ−アリ
ルジ（メタ）アリルアミン、Ｎ−ヒドロキシエチルジ（
メタ）アリルアミン、Ｎ−ベンジルジ（メタ）アリルア
ミン、Ｎ−シクロへキシルジ（メタ）アリルアミン等が
挙げられる。また、無機酸及び有機酸としては上記と同
様のものを例示できる。The N-substituted tertiary diallylamine derivative of formula [1] has N
a third having a substituent R2 and two (meth)allyl groups;
Examples of the tertiary amine include N-methyldi(meth)allylamine, N-ethyldi(meth)amylamine, N-probyldi(meth)allylamine, N-butyldi(meth)allylamine, N-allyldi(meth)allylamine, N-hydroxyethyldi(
Examples include meth)allylamine, N-benzyldi(meth)allylamine, and N-cyclohexyldi(meth)allylamine. Moreover, the same inorganic acids and organic acids as mentioned above can be exemplified.
本発明の方法に使用される共重合物は、［Ｉ］のモノマ
ーと［ｎｌのモノマーとを、モル比１：９〜９：１の割
合で用い、公知のラジカル共重合法に従って合成される
。用いられるラジカル重合触媒としては、例えば過硫酸
アンモニウム・過硫酸カリウム、過酸化水素、ベンゾイ
ル／＜−オ＋サイド、第三級ブチルハイドロパーオキサ
イド、アゾビスイソブチロニトリル、クメンパーオキサ
イド等を例示できる。勿論、触媒としてはこれらに限定
されるものではない。また、溶媒としては水或いはメタ
ノール、エタノール、イソプロパツール、ｎ−プロパツ
ール、ホルムアミド、ジメチルホルムアミド、ジオキサ
ン、アセトニトリル、ジメチルスルホキシド等の極性溶
媒を例示し得る。The copolymer used in the method of the present invention is synthesized according to a known radical copolymerization method using the monomer [I] and the monomer [nl in a molar ratio of 1:9 to 9:1. . Examples of the radical polymerization catalyst used include ammonium persulfate/potassium persulfate, hydrogen peroxide, benzoyl/<-o+side, tertiary butyl hydroperoxide, azobisisobutyronitrile, cumene peroxide, etc. . Of course, the catalyst is not limited to these. Examples of the solvent include water or polar solvents such as methanol, ethanol, isopropanol, n-propanol, formamide, dimethylformamide, dioxane, acetonitrile, and dimethyl sulfoxide.
かくして得られる共重合物の数平均重合度はセファデッ
クスＧ−２５及びセファデックスＧ−５０（ファルマシ
ア ファインケミカルズ社製、スウェーデン）を充填剤
としたゲル濾過法により測定して１０〜３０００程度、
好ましくは２０〜１０００程度である。。The number average degree of polymerization of the copolymer thus obtained is about 10 to 3000, as measured by gel filtration using Sephadex G-25 and Sephadex G-50 (manufactured by Pharmacia Fine Chemicals, Sweden) as fillers.
Preferably it is about 20 to 1000. .
本発明の被染物処理方法としては、従来より公知の方法
を適宜利用できる。例えば上記共重合物を染色物重量の
０．０１〜１重量％程度溶解させた水溶液中に染色物を
浸漬した後乾燥させる方法又は上記共重合物を１〜５ｆ
ｆｉ量％程度含む水溶液でパッド処理する方法等を例示
できる。浸漬処理の場合、通常浴比は１：１０〜１：３
０程度、処理温度は２０〜７０℃程度、処理時間は１０
〜２０分程度である。As the method for treating the dyed object of the present invention, conventionally known methods can be used as appropriate. For example, a method in which the dyed product is immersed in an aqueous solution containing about 0.01 to 1% by weight of the dyed product and then dried, or a method in which the above copolymer is dissolved in an amount of 1 to 5 f
Examples include a method of pad treatment with an aqueous solution containing about % fi. In the case of immersion treatment, the bath ratio is usually 1:10 to 1:3.
0, processing temperature is about 20-70℃, processing time is 10
~20 minutes.
発明の効果
本発明の方法によって処理された染色物は、従来法によ
って処理された染色物の有する問題点がすべて解消され
たものであり、湿潤堅牢度、耐塩素堅牢度、耐光堅牢度
等の染色堅牢度が著しく向上した上で、樹脂加工、熱処
理等による変色もほとんど認められない。即ち、染色堅
牢度が著しく向上していると同時に、樹脂加工、熱処理
等による染色物の色相の変化や捺染物の白湯の黄変等が
著しく少ないものである。Effects of the Invention The dyed products processed by the method of the present invention are free from all the problems of dyed products processed by conventional methods, and have excellent wet fastness, chlorine fastness, light fastness, etc. In addition to significantly improved color fastness, there is almost no discoloration due to resin processing, heat treatment, etc. That is, the color fastness is significantly improved, and at the same time, changes in the hue of the dyed product due to resin processing, heat treatment, etc. and yellowing of the hot water of the printed product are significantly reduced.
本発明をより一層明瞭なものとするため、参考例、比較
例参考例及び実施例を挙げる。In order to make the present invention even clearer, reference examples, comparative examples, and examples are given.
参考例 １
反応容器中にＮ−メチルアリルアミン塩酸塩１０７．５
ｇ （１モル）とＮ−メチルジアリルアミン塩酸塩１４
７．５ｇ （１モル）、水２５５ｇを投入し攪拌して十
分に混合溶解した。次に過硫酸アンモニウム３ｇを加え
て窒素ガスを通じながら７０〜７５℃で４０時間反応を
行った後、臭素化法により反応率を測定したところ７０
％であった。続いて内容物を室温まで冷却し、得られた
黄色透明釉ちょう液を多量のアセトン中に加え重合物を
沈澱させた。沈澱物をろ取し、更にアセトンで数回洗浄
した後、減圧乾燥して共重合物１７３ｇ（６８％）を得
た。このものの数平均重合度は約２５０であった。Reference example 1 N-methylallylamine hydrochloride 107.5% in reaction vessel
g (1 mol) and N-methyldiallylamine hydrochloride 14
7.5 g (1 mole) and 255 g of water were added and stirred to thoroughly mix and dissolve. Next, 3 g of ammonium persulfate was added and the reaction was carried out at 70 to 75°C for 40 hours while passing nitrogen gas, and the reaction rate was measured by the bromination method.
%Met. Subsequently, the contents were cooled to room temperature, and the obtained yellow transparent glaze liquid was added to a large amount of acetone to precipitate a polymer. The precipitate was collected by filtration, washed several times with acetone, and then dried under reduced pressure to obtain 173 g (68%) of a copolymer. The number average degree of polymerization of this product was about 250.
参考例 ２
反応容器中にＮ−メチルアリルアミン塩酸塩５３．７５
ｇ （０，５モル）とＮ−メチルジアリルアミン塩酸塩
１４７．５ｇ （１モル）、水２０１．２５ｇを投入し
攪拌して十分に混合溶解した。次に過硫酸アンモニウム
３ｇを加えて攪拌溶解した。次いで、窒素ガスを通じな
がら７０〜７５℃で３５時間反応を行った後、臭素化法
により反応率を測定したところ７２％であった。続いて
内容物を室温まで冷却し、得られた黄色透明釉ちょう液
を多量のアセトン中に加え重合物を沈澱させた。沈澱物
をろ取し、更にアセトンで数回洗浄した後、減圧乾燥し
て共重合物１４１ｇ（，７０％）を得た。このものの数
平均重合度は約３５０であった。Reference example 2 N-methylallylamine hydrochloride 53.75% in reaction vessel
g (0.5 mol), 147.5 g (1 mol) of N-methyldiallylamine hydrochloride, and 201.25 g of water were added and stirred to thoroughly mix and dissolve. Next, 3 g of ammonium persulfate was added and dissolved with stirring. Next, the reaction was carried out at 70 to 75° C. for 35 hours while passing nitrogen gas, and then the reaction rate was measured by the bromination method and found to be 72%. Subsequently, the contents were cooled to room temperature, and the obtained yellow transparent glaze liquid was added to a large amount of acetone to precipitate a polymer. The precipitate was collected by filtration, washed several times with acetone, and then dried under reduced pressure to obtain 141 g (70%) of a copolymer. The number average degree of polymerization of this product was about 350.
参考例 ３
反応容器中にＮ−シクロへキシルアリルアミン塩酸塩８
７．７５ｇ （０，５モル）とＮ−メチルジアリルアミ
ン塩酸塩１４７．５ｇ （１モル）、水２３５．２５ｇ
を投入し攪拌して十分に混合溶解した。次に過硫酸アン
モニウム３ｇを加えテ攪拌溶解した。次いで窒素ガスを
通じながら７０〜７５℃で４５時間反応を行った後、臭
素化法により反応率を測定したところ６６％であった。Reference example 3 N-cyclohexylallylamine hydrochloride 8 in the reaction vessel
7.75 g (0.5 mol), 147.5 g (1 mol) of N-methyldiallylamine hydrochloride, and 235.25 g of water.
was added and stirred to thoroughly mix and dissolve. Next, 3 g of ammonium persulfate was added and dissolved with stirring. Next, the reaction was carried out at 70 to 75° C. for 45 hours while passing nitrogen gas, and the reaction rate was measured by the bromination method and found to be 66%.
続いて内容物を室温まで冷却し、得られた黄色透明釉ち
ょう液を多量のアセトン中に加え重合物を沈澱させた。Subsequently, the contents were cooled to room temperature, and the obtained yellow transparent glaze liquid was added to a large amount of acetone to precipitate a polymer.
沈澱物をろ取し、更にアセトンで数回洗浄した後、減圧
乾燥して共重合物１５３ｇ （６５％）を得た。このも
のの数平均重合度は約２００であった。The precipitate was collected by filtration, washed several times with acetone, and then dried under reduced pressure to obtain 153 g (65%) of a copolymer. The number average degree of polymerization of this product was about 200.
参考例 ４
反応容器中にＮ−メチルメタアリルアミン塩酸塩６０．
７５ｇ （０，５モル）とＮ−メチルジアリルアミン塩
酸塩１４７．５ｇ （１モル）、水２０８．２５ｇを投
入し攪拌して十分に混合溶解した。次に過硫酸アンモニ
ウム３ｇを投入し攪拌溶解した。次いで窒素ガスを通じ
ながら７０〜７５℃で４５時間反応を行った後、臭素化
法により反応率を測定したところ７５％であった。続い
て内容物を室温まで冷却し、得られた黄色透明釉ちょう
液を多量のアセトン中に加え重合物を沈澱させた。沈澱
物をろ取し、更にアセトンで数回洗浄した後、減圧乾燥
して共重合物１５２ｇ （７３％）を得た。このものの
数平均重合度は約３３０であった。Reference Example 4 N-methylmethallylamine hydrochloride 60% in a reaction vessel.
75 g (0.5 mol), 147.5 g (1 mol) of N-methyldiallylamine hydrochloride, and 208.25 g of water were added and stirred to thoroughly mix and dissolve. Next, 3 g of ammonium persulfate was added and dissolved with stirring. Next, the reaction was carried out at 70 to 75° C. for 45 hours while passing nitrogen gas, and then the reaction rate was measured by the bromination method and found to be 75%. Subsequently, the contents were cooled to room temperature, and the obtained yellow transparent glaze liquid was added to a large amount of acetone to precipitate a polymer. The precipitate was collected by filtration, washed several times with acetone, and then dried under reduced pressure to obtain 152 g (73%) of a copolymer. The number average degree of polymerization of this product was about 330.
比較参考例１
特公昭５８−２０１８１１号に記載の方法に従いアリル
アミン塩酸塩の重合反応を行い、単独重合源の得た。Comparative Reference Example 1 A homopolymerization source was obtained by carrying out a polymerization reaction of allylamine hydrochloride according to the method described in Japanese Patent Publication No. 58-201811.
比較参考例２
特公昭６０−１９２７１５号に記載の方法に準じＮ−メ
チルアリルアミン塩酸塩の重合反応を行い、単独重合物
を得た。Comparative Reference Example 2 A polymerization reaction of N-methylallylamine hydrochloride was carried out according to the method described in Japanese Patent Publication No. 60-192715 to obtain a homopolymer.
比較参考例３
反応容器中にＮ−メチルジアリルアミン塩酸塩１４７．
５ｇ （１モル）、水９８ｇ１過硫酸アンモニウム２ｇ
を投入し、窒素ガスを通じながら７０〜７５℃で８時間
反応を行った後、臭素化法により反応率を測定したとこ
ろ９８％であった。Comparative Reference Example 3 N-methyldiallylamine hydrochloride 147.
5g (1 mole), 98g water1 2g ammonium persulfate
was charged and the reaction was carried out at 70 to 75° C. for 8 hours while passing nitrogen gas, and the reaction rate was measured by the bromination method and found to be 98%.
続いて、内容物を室温まで冷却し、得られた黄色透明粘
ちょう液を多量のアセトン中に加え重合物を沈澱させた
。沈澱物をろ取し、更にアセトンで数回洗浄した後、減
圧乾燥して単独重合物１４３ｇ（９７％）を得た。Subsequently, the contents were cooled to room temperature, and the resulting yellow transparent viscous liquid was added to a large amount of acetone to precipitate a polymer. The precipitate was collected by filtration, washed several times with acetone, and then dried under reduced pressure to obtain 143 g (97%) of a homopolymer.
比較参考例４
特公昭６０−８８０１８号に記載の方法に準じアリルア
ミン塩酸塩９３．５ｇ （１モル）とＮ−メチルアリル
アミン塩酸塩１０７．５ｇ （１モル）を反応させ共重
合物１９３ｇ （収率９６％）を得た。Comparative Reference Example 4 93.5 g (1 mol) of allylamine hydrochloride and 107.5 g (1 mol) of N-methylallylamine hydrochloride were reacted according to the method described in Japanese Patent Publication No. 60-88018 to produce 193 g (yield) of a copolymer. 96%).
比較参考例５
特公昭６０−８８０１８号に記載の方法に準じＮ−メチ
ルアリルアミン塩酸塩１０７．５ｇ （１モル）とジア
リルアミン塩酸塩２５３． ５ｇ （１モル）を反応さ
せ共重合物３４３ｇ （収率９５％）を得た。Comparative Reference Example 5 107.5 g (1 mol) of N-methylallylamine hydrochloride and 253 g of diallylamine hydrochloride were prepared according to the method described in Japanese Patent Publication No. 60-88018. 5 g (1 mol) was reacted to obtain 343 g (yield: 95%) of a copolymer.
比較参考例６
特公昭６０−８８０１８号に記載の方法に準じＮ−メチ
ルアリルアミン塩酸塩１０７．５ｇ （１モル）とＮ、
Ｎ−ジメチルジアリルアンモニウムクロライド２８１
．５ｇ （１モル）を反応させ共重合物３７０ｇ （収
率９５％）を得た。Comparative Reference Example 6 107.5 g (1 mol) of N-methylallylamine hydrochloride and N,
N-dimethyldiallylammonium chloride 281
．． 5 g (1 mole) was reacted to obtain 370 g (yield 95%) of a copolymer.
実施例
前記参考例１〜４及び比較参考例１〜６で得られたそれ
ぞれの共重合物及び単独重合物を下記方法に従って処理
し、以下の性能試験を行った。Examples The respective copolymers and homopolymers obtained in Reference Examples 1 to 4 and Comparative Reference Examples 1 to 6 were treated according to the following method, and the following performance tests were conducted.
（イ）処理変色、湿潤堅牢度、耐塩素堅牢度、耐光堅牢
度の各試験用試験布の作成性
常法に従い浸漬法にて反応染料で染色された染色布を、
前記の共重合物又は単独重合物の０．０５重量％水溶液
に浴比１：２０、温度６０℃で２０分間浸漬処理した後
、水洗し風乾させ試験布とした。(a) Preparation of test cloths for each test of treatment discoloration, wet fastness, chlorine fastness, and light fastness A dyed cloth dyed with a reactive dye by the dipping method according to a conventional method,
The test cloth was immersed in a 0.05% by weight aqueous solution of the copolymer or homopolymer at a bath ratio of 1:20 and a temperature of 60° C. for 20 minutes, then washed with water and air-dried.
（ロ）樹脂加工及び熱処理による変色試験用試験布の作
成法
前記の共重合物及び単独重合物の１．０重量％水溶液を
調製し、Ｌｅｖａｆｉｘ Ｂｒ１１１． ＢｌｕｅＥ
ＢＲＡ Ｏ，２％濃度染色綿布及び綿白布を絞り率６
０％でパッド処理後１００℃で２分間乾燥させ試験布と
した。(b) Method for preparing test cloth for discoloration test by resin processing and heat treatment A 1.0% by weight aqueous solution of the above-mentioned copolymer and homopolymer was prepared, and Levafix Br111. BlueE
BRA O, 2% density dyed cotton fabric and white cotton fabric squeezing rate 6
After pad treatment with 0%, the cloth was dried at 100° C. for 2 minutes to obtain a test cloth.
（ハ）性能試験法
前記試験布を使、用し、次の方法に従って諸性能の判定
を行った。(c) Performance test method Using the above test cloth, various performances were evaluated according to the following methods.
ａ）処理変色
堅牢度向上剤処理布と染色原布を肉眼にて比較し、変退
色用グレー・スケールにて級数判定した。a) Treatment Discoloration Fastness Improver The treated fabric and the dyed original fabric were compared with the naked eye, and the series was evaluated using the gray scale for discoloration and fading.
ｂ）湿潤堅牢度試験
耐洗濯堅牢度をもって湿潤堅牢度とした。即ち、Ｊ Ｉ
５−Ｌ−０８４４Ａ−ＩＶ号、添付白布として綿金巾
、絹羽二重を用い、その汚染度を汚染用グレー・スケー
ルにて級数判定゛した。b) Wet fastness test Wet fastness was defined as washing fastness. That is, J I
No. 5-L-0844A-IV, a cotton gold cloth and a silk habutae were used as the attached white cloth, and the degree of contamination was evaluated using a contamination gray scale.
Ｃ）耐塩素堅牢度
ｃ−１）
Ｊ Ｉ ５−Ｌ−０８２１に従い、有効塩素として２０
ｐｐｍを含むｐＨ７，５±０．２の緩衝液に試験布を浸
漬し、２７℃で１時間洗濯試験機にかける。その後流水
中で５分間洗い脱水乾燥した試験布の変退色を変退色用
グレー・スケールにて級数判定した。C) Chlorine fastness c-1) According to J I 5-L-0821, 20% as available chlorine
The test fabric is immersed in a pH 7.5 ± 0.2 buffer solution containing ppm and placed in a washing tester at 27° C. for 1 hour. Thereafter, the test cloth was washed in running water for 5 minutes, dehydrated and dried, and the discoloration and fading of the test cloth was evaluated using a gray scale for discoloration and fading.
ｃ−２）
水道水流入量６リツトル／分とし家庭用洗濯機で１時間
連続水洗した試験布の変退色を変退色用グレー・スケー
ルにて級数判定した。c-2) The discoloration and fading of the test cloth which was washed continuously for 1 hour in a household washing machine with an inflow of tap water of 6 liters/min was evaluated using a gray scale for discoloration and fading.
ｄ）耐光堅牢度
Ｊ Ｉ ５−Ｌ−０８４２、フェードメータ２０時間照
射後、試験布の変退色を変退色用グレー・スケールにて
級数判定した。d) Light fastness J I 5-L-0842, fade meter After 20 hours of irradiation, the color change and fading of the test fabric was evaluated using a gray scale for color change and fading.
ｅ）樹脂加工及び熱処理による変色試験ｅ−１）
［リケンレジンＭＳ−１１０ｊ （三木理研（株）製
、グリオキザール系樹脂）を８重量％、「リケンフィク
サーＭＸ−２Ｊ （三木理研（株）製、樹脂加工用触
媒）を３重量％含有する水溶液を調製し試験布を絞り率
８５％でパッド処理し１００℃で３分間乾燥後１７０℃
で３０秒間熱処理を行い、試験布の変退色を変退色用グ
レー・スケールにて級数判定した。e) Discoloration test due to resin processing and heat treatment e-1) [8% by weight of Riken Resin MS-110j (manufactured by Miki Riken Co., Ltd., glyoxal-based resin), "Riken Fixer MX-2J (manufactured by Miki Riken Co., Ltd., resin) An aqueous solution containing 3% by weight of a processing catalyst) was prepared, a test cloth was padded at a squeezing rate of 85%, dried at 100°C for 3 minutes, and then heated at 170°C.
The test fabric was heat-treated for 30 seconds, and the discoloration and fading of the test fabric was evaluated using a gray scale for discoloration and fading.
ｅ−２）
試験布を１７０℃で３０秒間熱処理を行い、その熱変色
を変退色用グレー・スケールにて級数判定した。e-2) The test fabric was heat-treated at 170°C for 30 seconds, and the thermal discoloration was evaluated using a gray scale for discoloration and fading.
以上の試験結果を第１表、第２表、第３表及び第４表に
示す。用いた染料は各表の上に示した通りである。The above test results are shown in Tables 1, 2, 3 and 4. The dyes used are as shown above each table.
第 ４ 表
樹脂加工及び熱処理による変色試験
第１表〜第４表より明らかな様に、本発明方法によって
処理された染色布は、樹脂加工処理及び熱処理による変
色が極めて少なく、且つ耐塩素堅牢度、湿潤堅牢度、耐
光堅牢度等を高水準にて満足させ得るのに対し、従来法
では樹脂加工処理及び熱処理による変色が少ないことと
上記３つの堅牢度とを同時に満足させる染色布は得られ
ていない。Table 4 Discoloration test due to resin processing and heat treatment As is clear from Tables 1 to 4, the dyed fabric treated by the method of the present invention shows extremely little discoloration due to resin processing and heat treatment, and has high chlorine fastness. , wet fastness, light fastness, etc. can be satisfied at a high level, whereas conventional methods cannot produce a dyed fabric that simultaneously satisfies the above three fastnesses with little discoloration due to resin processing and heat treatment. Not yet.
（以 上） 代理人 弁理士 三 枝 英 二６″′鬼、−、ノ １−＋(that's all) Agent Patent Attorney Eiji Sane 26″′oni, -, ノ 1-+
Claims (1)
維からなる繊維材料の反応染料による染色物を、下記［
I ］で表わされるモノマーと下記［II］で表わされる
モノマーとをモル比１：９〜９：１の割合で共重合させ
て得た共重合物で後処理することを特徴とする染色物の
染色堅牢度向上方法。 ［ I ］式 ▲数式、化学式、表等があります▼ ［式中、Ｒ＿１は水素原子又はメチル基を示す。 Ｒ＿２はＣ＿１〜Ｃ＿６のアルキル基、ベンジル基、ヒ
ドロキシエチル基又はシクロアルキル基を示す。ＨＸは
無機酸又は有機酸を示す。］で表わされるＮ−置換第２
級アリルアミン誘導体。 ［II］式 ▲数式、化学式、表等があります▼ ［式中、Ｒ＿３及びＲ＿４は同一又は相異なつて水素原
子又はメチル基を示す。Ｒ＿２及びＨＸは前記に同じ。 ］で表わされるＮ−置換第３級ジアリルアミン誘導体。(1) Dyed products using reactive dyes of cellulose fibers or fiber materials consisting of cellulose fibers and other fibers as shown below [
A dyed product characterized by being post-treated with a copolymer obtained by copolymerizing a monomer represented by [I] and a monomer represented by [II] below at a molar ratio of 1:9 to 9:1. Method for improving color fastness. [I] Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_1 represents a hydrogen atom or a methyl group. R_2 represents a C_1 to C_6 alkyl group, benzyl group, hydroxyethyl group, or cycloalkyl group. HX represents an inorganic acid or an organic acid. ] N-substituted second
grade allylamine derivative. [II] Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_3 and R_4 are the same or different and represent a hydrogen atom or a methyl group. R_2 and HX are the same as above. ] N-substituted tertiary diallylamine derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62011021A JPS63182485A (en) | 1987-01-19 | 1987-01-19 | Enhancement of dyeing fastness |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62011021A JPS63182485A (en) | 1987-01-19 | 1987-01-19 | Enhancement of dyeing fastness |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63182485A true JPS63182485A (en) | 1988-07-27 |
Family
ID=11766452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62011021A Pending JPS63182485A (en) | 1987-01-19 | 1987-01-19 | Enhancement of dyeing fastness |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63182485A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0280681A (en) * | 1988-09-16 | 1990-03-20 | Nitto Boseki Co Ltd | Dye fixing agent for direct dye |
| JPH07292583A (en) * | 1994-08-31 | 1995-11-07 | Nitto Boseki Co Ltd | Dye-fixing agent for direct dye |
| EP0685591A4 (en) * | 1992-06-17 | 1996-11-13 | Nicca Chemical Co | Dye fixing agent. |
-
1987
- 1987-01-19 JP JP62011021A patent/JPS63182485A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0280681A (en) * | 1988-09-16 | 1990-03-20 | Nitto Boseki Co Ltd | Dye fixing agent for direct dye |
| EP0685591A4 (en) * | 1992-06-17 | 1996-11-13 | Nicca Chemical Co | Dye fixing agent. |
| US5653772A (en) * | 1992-06-17 | 1997-08-05 | Nicca Chemical Co., Ltd. | Method of fixing cellulose fibers dyed with a reactive dye |
| JPH07292583A (en) * | 1994-08-31 | 1995-11-07 | Nitto Boseki Co Ltd | Dye-fixing agent for direct dye |
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