JPS6122076B2

JPS6122076B2 -

Info

Publication number: JPS6122076B2
Application number: JP56028980A
Authority: JP
Inventors: Sumyuki Shimohiro; Akio Murata; Choko Nishioka
Original assignee: Dainippon Pharmaceutical Co Ltd
Current assignee: Sumitomo Pharma Co Ltd
Priority date: 1981-02-27
Filing date: 1981-02-27
Publication date: 1986-05-30
Also published as: JPS57143583A

Description

[Detailed description of the invention]

本発明は反応性染料で染色された綿繊維製品の
塩素堅牢度増進に用いる組成物及びその使用方法
に関する。反応性染料は色相が鮮明なこと及び湿潤堅牢度
が良好なことにより、近年その使用量は着実に増
加している。しかしながら、この反応性染料は塩
素堅牢度が弱いという欠点を有している。即ち、
反応性染料で染色した綿繊維製品は、水道水中の
微量活性塩素の作用により染料が酸化され、退色
したり変色したりする場合が非常に多い。この欠点を解消するために、従来、繊維製品を
樹脂類と抗酸化作用を有する物質で処理する方法
（特開昭50−53693、同50−58373、同50−58374及
び同50−58395）及び繊維をポリエチレンポリア
ミンとエピハロヒドリンを縮合させたポリマー等
で処理する方法（特開昭55−152879、同55−
152880及び同55−152881）が提案されているが、
前者は効果の持続性は認められるものの高熱処理
を必要とし省エネルギー面から好ましくなく、後
者は効果の持続性そのものが弱い点で不都合であ
る。本発明者等は、上述のような問題点を解決する
ため種々の抗酸化剤に着目し、研究を行なつたと
ころ、少なくとも次の２点が塩素堅牢度を増進す
るのに必要であることを見出した。塩素堅牢度を増進させるための化合物の酸化
還元電位が、反応性染料の電位よりも低く、か
つその化合物の酸化される速度が反応性染料の
それより速いこと。該化合物の繊維に対する吸着量が大であり、
かつソーピング工程等で容易に繊維から脱落し
ないこと。の条件を満たす化合物として、レゾルシン、
ハイドロキノン、没食子酸、ピロガロール、五倍
子タンニン、タラタンニン、没食子タンニンなど
の多価フエノール類があられるが、これらはの
条件を満足しない。そこでの条件を得るために
該繊維と上記の多価フエノール類とを、カチオン
性化合物によつて結合せしめることを試みた。カ
チオン性化合物としては高級アルキルアミン類、
そのエピハロヒドリンとの重合体及び高級アルキ
ルアミド類等がある。しかし、これらの化合物に
は、反応性染料よりも酸化還元電位が高いものが
あり、それらはタンニン等の条件を満足せしめ
る性質を打消してしまうので好ましくないことが
わかつた。以上の知見をもとに、本発明者等は更に研究を
進め本発明を完成した。本発明は、 (1) Ｒ−NHCH₂CH₂CH₂NH₂（式中、Ｒは高級ア
ルキル基）で示されるアルキルプロピレンジア
ミンと加水分解型タンニンとを重量比１：0.3
〜９で混和してなることを特徴とする反応性染
料で染色された綿繊維製品の塩素堅牢度増進
剤、及び (2) 反応性染料で染色された綿繊維製品を、Ｒ−
NHCH₂CH₂CH₂NH₂（式中、Ｒは高級アルキル
基）で示されるアルキルプロピレンジアミンと
加水分解型タンニンとを重量比１：0.3〜９で
混和して得られる組成物で処理し、次いで金属
塩で処理すること（いわゆる２浴処理）よりな
る該繊維製品の塩素堅牢度増進方法。に関する。本発明の綿繊維製品とは、糸、編織物、不織布
等又は綿繊維と他繊維との混紡、混織、交編織品
等を意味する。本発明者等は、高級アルキルアミン等を上述し
たの性質を有するタンニン等に混和せしめて得
られる組成物で繊維製品を処理することを試み、
その結果、本発明のアルキルプロピレンジアミン
と加水分解型タンニンとを混和して得られる組成
物が塩素堅牢度増進に最適であることを見出し
た。Ｒ−NHCH₂CH₂CH₂NH₂（式中、Ｒは高級アル
キル基）で示されるアルキルプロピレンジアミン
としては、例えば牛脂アルキルプロピレンジアミ
ン、ヤシアルキルプロピレンジアミン、大豆アル
キルプロピレンジアミン、ラウリルプロピレンジ
アミン、ステアリルプロピレンジアミン、オレイ
ルプロピレンジアミンなどがあり、Ｒが同一の単
一化合物を常に用いなければならないことはな
い。本化合物は加水分解型タンニンを染色物に結
合せしめる働きを有している。加水分解型タンニンとしては、五倍子タンニ
ン、タラタンニン、没食子タンニン等があり、反
応性染料より先に酸化を受けることにより、反応
性染料そのものが酸化されるのを防ぐ効果を有し
ている。なお、レゾルシン、ハイドロキノン等は
加水分解型タンニンと同様の効果を有している
が、アルキルプロピレンジアミンによりほとんど
染色物に結合せしめることができず塩素堅牢度の
増強につながらない。アルキルプロピレンジアミンと加水分解型タン
ニンを混和せしめる方法は、通常、アルキルプロ
ピレンジアミンを酸性で水に溶解し、アルキルプ
ロピレンジアミン塩の水溶液を作り、他方加水分
解型タンニンを水に溶解しタンニン水溶液とし、
両者を均一混和すれば良い。その混和比は、タン
ニン類の重量（ｇ）／アルキルプロピレンジアミ
ンの重量（ｇ）をＲ_TAとすると、0.3＜Ｒ_TA＜
９、好ましくは0.7〜2.3である。Ｒ_TA≦0.3の場合
は効果が低減し、強い塩素堅牢度が要求される場
合は望ましくない。９≦Ｒ_TAの場合は混和して得
られた組成物が用時、水に難溶性又は不溶性とな
りスカム等が発生し繊維に付着するトラブルが生
じ用いられない。なお、アルキルプロピレンジアミンと加水分解
型タンニンを別個に用いて順次処理する方法によ
つても、繊維製品の塩素堅牢度を増進せしめ得
る。しかしこの方法では３浴を要するのに対し、
本発明では２浴で行ない得るという利点を有して
いる。金属塩は、加水分解型タンニンと難溶性の塩を
形成し得るものであつて、繊維に固定化するため
に用い、吐酒石、塩化アンチモン、酒石酸アンチ
モンナトリウム、塩化第一スズ、塩化第二スズ、
塩化アルミニウム、硫酸アルミニウム、硫酸第一
鉄、硫酸第二鉄、塩化亜鉛、硫酸銅などである。
なかでも、吐酒石、酒石酸アンチモンナトリウム
塩化アルミニウム、硫酸アルミニウムなどが好適
である。金属塩を使用しない場合は、ソーピング
工程時、又はくり返し洗濯時、加水分解型タンニ
ンが脱落し効果の低減をきたすため、塩素堅牢度
の持続性が要求される製品においては、使用は必
須である。本発明の組成物を用いて綿繊維製品を処理する
場合、その処理条件は反応性染料の種類、染色の
濃度などにより多少異なるが、組成物を0.1〜10
％o.w.f.、好ましくは0.5〜４％o.w.f.、浴比１：
10〜１：30で使用する。処理温度は５〜80℃であ
り、夏冬を問わず浴を加熱又は冷却せずに常温で
処理することができる。処理時間は10〜30分、処
理PHは２〜６である。金属塩による処理では、加水分解型タンニンの
0.1〜５倍量、好ましくは0.25〜0.5倍量の金属塩
を使用するが、その他の条件は組成物による処理
と同様である。本発明によれば、従来法では得られない塩素堅
牢度の飛躍的な増進及び持続を達成することがで
き、さらに浴を加熱又は冷却することなく、夏冬
を問わず常温で処理することができるので省エネ
ルギー化にきわめて有益である。また、反応性染
料で染色した繊維の利点である色相の鮮明さ、湿
潤堅牢度の良好さを損なうことがなく、酸加水分
解堅牢度については向上も見られる。本発明を更に詳細に説明するために、以下に実
施例を示す。実施例１牛脂アルキルプロピレンジアミン60部を酢酸50
部に撹拌溶解しＡ液とし、他方タラタンニン40部
を水50部に撹拌溶解しＢ液とし、Ａ液とＢ液とを
均一撹拌混合して組成物200部を得た。本組成物
は水に澄明に溶解した。実施例２ラウリルプロピレンジアミン50部を酢酸50部に
撹拌溶解しＡ液とし、他方五倍子タンニン50部を
水50部に撹拌溶解しＢ液とし、Ａ液とＢ液とを均
一撹拌混合して組成物200部を得た。本組成物は
水に澄明に溶解した。実施例３大豆アルキルプロピレンジアミン40部を酢酸50
部に撹拌溶解しＡ液とし、他方没食子タンニン60
部を水50部に撹拌溶解しＢ液とし、Ａ液とＢ液と
を均一撹拌混合して組成物200部を得た。本組成
物は水に澄明に溶解した。実施例４４（o.w.f.）の下記反応性染料で染色した綿ギ
ヤバを、実施例１で得られた組成物を用いて、処
理量２％（o.w.f.）、浴比１：50、PH５、温度25
℃で20分間浸漬処理した。続いて水洗後、該処理
綿ギヤバを吐酒石を用いて、処理量0.3％（o.w.f.
）、浴比１：50、温度25℃で20分間浸漬処理し、
水洗後、風乾した。用いた染料は、I.C.I社製レ
バフイツクスネイビーブルーＥ−2R、レバフイ
ツクスゴールデンイエローＥ−Ｇ、日本化薬製ミ
カシオンブリリアントブルーRS、サンド社製ド
リマレンブリリアントレツドＫ−4BLである。実施例５実施例２で得られた組成物を用いる実施例４と
同様にして、反応性染料で染色した綿ギヤバを処
理した。実施例６実施例３で得られた組成物を用いる他は実施例
４と同様にして、反応性染料で染色した綿ギヤバ
を処理した。実施例７組成物を実施例１で得たものに、温度を50℃に
変える以外は実施例４と同様にして、反応性染料
で染色した綿ギヤバを処理した。実施例８組成物を実施例２で得たものに、温度を５℃に
及び金属塩を硫酸アルミニウムに変える以外は実
施例４と同様にして、反応性染料で染色した綿ギ
ヤバを処理した。なお、実施例１〜３で処理した綿ギヤバの色相
は、未処理品とほとんど同程度であつた。参考例１実施例４と同一の反応性染料で染色した綿ギヤ
バを、タラタンニンを用いて、処理量２％（o.w.
f.）、浴比１：50、PH５、温度25℃で20分間浸漬
処理した。続いて水洗後、該処理綿ギヤバを吐酒
石を用いて、処理量0.6％（o.w.f.）、浴比１：
50、PH５、温度25℃で20分間浸漬処理し水洗後、
風乾した。参考例２実施例４と同一の反応性染料で染色した綿ギヤ
バを、牛脂アルキルプロピレンジアミンを用い
て、処理量２％（o.w.f.）、浴比１：50、PH５、
温度25℃で20分間浸漬処理し水洗後、風乾した。参考例３実施例４と同一の反応性染料で染色した綿ギヤ
バを、実施例１で得られた組成物を用いて、処理
量２％（o.w.f.）、浴比１：50、PH５、温度25℃
で20分間浸漬処理し水洗後、風乾した。実施例９実施例４〜８、参考例１〜３で得られた処理綿
ギヤバに対して、下記染色堅牢度試験を行なつ
た。塩素堅牢度試験 (1) 有効塩素50ppmを含むPH８の緩衝液に試験片
を浴比１：100で浸漬し、25℃で２時間撹拌後、
水洗し乾燥した。試験片の変退色の判定はJIS−
Ｌ−0801の10によつた。結果を下記表に示す。塩素堅牢度試験 (2) 市販の酸素系漂白剤入り洗剤（商品名「花王ポ
ピンズ」）の３ｇ/、50℃の水溶液に試験片を浴
比１：100で浸漬し、50℃で30分間撹拌後、水洗
する操作を６回行つた後、塩素堅牢度試験(1)に記
載する操作を行つた。本試験における結果の判定
もJIS−Ｌ−0801の10によつた。結果を下記表に
示す。酸加水分解堅牢度試験乳酸10ｇ/の水溶液に、試験片及び添付白布
（綿）を浴比１：100で浸漬し、60℃で20分間撹拌
後、水洗し乾燥した。本試験の添付白布の汚染の
判定はJIS−Ｌ−0801の10によつた。結果を下記
表に示す。結果から明らかなように、未処理布に比べ、タ
ンニン−金属塩処理布では塩素堅牢度はあまり増
進していないのに対し、本発明の組成物処理布で
は格段に増進している。更に本発明の組成物−金
属塩処理布では効果の持続性をも認められる。ま
たアルキルプロピレンジアミン単独処理において
は、酸加水分解堅牢度の増進は認められるが、塩
素堅牢度の増進はそれ程認められない。 The present invention relates to compositions and methods of use for enhancing the chlorine fastness of cotton textiles dyed with reactive dyes. The amount of reactive dyes used has steadily increased in recent years due to their vivid hues and good wet fastness. However, this reactive dye has the disadvantage of poor chlorine fastness. That is,
Cotton fiber products dyed with reactive dyes often fade or change color due to the dye being oxidized by the action of trace amounts of active chlorine in tap water. In order to eliminate this drawback, conventional methods include treating textile products with resins and substances that have an antioxidant effect (Japanese Patent Application Laid-Open Nos. 50-53693, 50-58373, 50-58374 and 50-58395); A method of treating fibers with a polymer made by condensing polyethylene polyamine and epihalohydrin (Japanese Patent Application Laid-Open No. 152879, 1983, 55-
152880 and 55-152881) have been proposed,
Although the former has a long-lasting effect, it requires high-temperature treatment and is unfavorable from an energy-saving perspective, while the latter is disadvantageous in that the long-lasting effect itself is weak. In order to solve the above-mentioned problems, the present inventors focused on various antioxidants and conducted research, and found that at least the following two points are necessary to improve chlorine fastness. I found out. The redox potential of the compound for enhancing chlorine fastness is lower than the potential of the reactive dye, and the rate at which the compound is oxidized is faster than that of the reactive dye. The amount of adsorption of the compound to fibers is large;
In addition, it should not easily fall off from the fibers during the soaping process, etc. As a compound that satisfies the conditions, resorcinol,
There are polyhydric phenols such as hydroquinone, gallic acid, pyrogallol, pentad tannin, cod tannin, and gallic tannin, but these do not satisfy the condition. In order to obtain such conditions, an attempt was made to bond the fibers and the above-mentioned polyhydric phenols using a cationic compound. Cationic compounds include higher alkylamines,
Examples include polymers with epihalohydrin and higher alkylamides. However, some of these compounds have a higher redox potential than the reactive dyes, and it has been found that these compounds are undesirable because they cancel out the properties of tannins and the like that satisfy the conditions. Based on the above knowledge, the present inventors conducted further research and completed the present invention. The present invention is characterized in that: (1) alkylpropylene diamine represented by R-NHCH ₂ CH ₂ CH ₂ NH ₂ (wherein R is a higher alkyl group) and hydrolyzable tannin at a weight ratio of 1:0.3;
(2) A chlorine fastness enhancer for cotton textile products dyed with a reactive dye, characterized in that it is mixed with R-
Treated with a composition obtained by mixing an alkylpropylene diamine represented by NHCH ₂ CH ₂ CH ₂ NH ₂ (wherein R is a higher alkyl group) and a hydrolyzable tannin at a weight ratio of 1:0.3 to 9, A method for improving the chlorine fastness of the textile product, which comprises subsequently treating it with a metal salt (so-called two-bath treatment). Regarding. The cotton fiber products of the present invention refer to yarns, knitted fabrics, non-woven fabrics, etc., or blends, blends, mixed knits, and woven fabrics of cotton fibers and other fibers. The present inventors attempted to treat textile products with a composition obtained by mixing higher alkyl amines and the like with tannins having the above-mentioned properties.
As a result, it has been found that a composition obtained by mixing the alkylpropylene diamine of the present invention and a hydrolyzable tannin is optimal for improving chlorine fastness. Examples of the alkylpropylene diamine represented by R-NHCH ₂ CH ₂ CH ₂ NH ₂ (wherein R is a higher alkyl group) include beef tallow alkylpropylene diamine, coconut alkylpropylene diamine, soybean alkylpropylene diamine, laurylpropylene diamine, and stearyl. Examples include propylene diamine and oleylpropylene diamine, and it is not always necessary to use a single compound with the same R. This compound has the function of binding hydrolyzable tannins to dyed materials. Hydrolyzable tannins include fivefold tannin, cod tannin, gallic tannin, and the like, which have the effect of preventing the reactive dye itself from being oxidized by being oxidized before the reactive dye. Note that resorcinol, hydroquinone, etc. have the same effect as hydrolyzed tannins, but due to the alkylpropylene diamines, they are hardly able to bind to the dyed material and do not lead to enhancement of chlorine fastness. The method for mixing alkylpropylene diamine and hydrolyzable tannin is usually to dissolve the alkylpropylene diamine in acidic water to create an aqueous solution of the alkylpropylene diamine salt, and then dissolve the hydrolyzable tannin in water to form an aqueous tannin solution.
It is sufficient to uniformly mix both. The mixing ratio is 0.3< _RTA <, where _RTA is the weight (g) of tannins/weight (g) of alkylpropylene diamine.
9, preferably 0.7 to 2.3. When R _TA ≦0.3, the effectiveness decreases, which is not desirable when strong chlorine fastness is required. In the case of 9≦R _TA , the composition obtained by mixing becomes poorly soluble or insoluble in water when used, and troubles such as scum and the like are generated and it adheres to fibers, so that it cannot be used. Note that the chlorine fastness of textile products can also be improved by a method in which alkylpropylene diamine and hydrolyzable tannin are used separately and treated sequentially. However, this method requires three baths;
The present invention has the advantage that it can be carried out in two baths. Metal salts can form poorly soluble salts with hydrolyzable tannins, and are used for immobilization on fibers. tin,
These include aluminum chloride, aluminum sulfate, ferrous sulfate, ferric sulfate, zinc chloride, and copper sulfate.
Among these, tartarite, antimony sodium tartrate, aluminum chloride, aluminum sulfate, and the like are preferred. If metal salts are not used, hydrolyzed tannins will fall off during the soaping process or repeated washing, reducing the effectiveness, so use is essential for products that require long-lasting chlorine fastness. . When treating cotton textile products using the composition of the present invention, the treatment conditions vary depending on the type of reactive dye, dyeing concentration, etc.
%owf, preferably 0.5-4%owf, bath ratio 1:
Use from 10 to 1:30. The treatment temperature is 5 to 80°C, and the treatment can be carried out at room temperature regardless of summer or winter without heating or cooling the bath. The treatment time is 10 to 30 minutes, and the treatment pH is 2 to 6. Treatment with metal salts reduces the amount of hydrolyzed tannins.
The metal salt is used in an amount of 0.1 to 5 times, preferably 0.25 to 0.5 times, but other conditions are the same as for the treatment with the composition. According to the present invention, it is possible to dramatically improve and maintain chlorine fastness that cannot be obtained with conventional methods, and furthermore, the bath can be treated at room temperature regardless of summer or winter without heating or cooling the bath. This is extremely beneficial for energy saving. In addition, the advantages of fibers dyed with reactive dyes, such as brightness of hue and good wet fastness, are not impaired, and the fastness to acid hydrolysis is improved. Examples are shown below to explain the present invention in more detail. Example 1 60 parts of beef tallow alkylpropylene diamine and 50 parts of acetic acid
On the other hand, 40 parts of cod tannin was stirred and dissolved in 50 parts of water to obtain a solution B, and the solutions A and B were uniformly mixed with stirring to obtain 200 parts of a composition. The composition dissolved clearly in water. Example 2 50 parts of lauryl propylene diamine were stirred and dissolved in 50 parts of acetic acid to obtain liquid A, and 50 parts of pentadol tannin was stirred and dissolved in 50 parts of water to form liquid B, and liquids A and B were uniformly stirred and mixed to form a composition. Obtained 200 copies. The composition dissolved clearly in water. Example 3 40 parts of soybean alkylpropylene diamine and 50 parts of acetic acid
Stir and dissolve in one part to make liquid A, and in the other part gallic tannin 60
1 part was stirred and dissolved in 50 parts of water to obtain liquid B, and liquid A and liquid B were uniformly mixed with stirring to obtain 200 parts of a composition. The composition dissolved clearly in water. Example 4 Cotton gear dyed with the following reactive dye of 4 (OWF) was dyed using the composition obtained in Example 1, treatment amount 2% (OWF), bath ratio 1:50, PH 5, temperature 25
It was soaked at ℃ for 20 minutes. Subsequently, after washing with water, the treated cotton gear was treated with tartar to reduce the treatment amount to 0.3% (owf).
), soaked for 20 minutes at a bath ratio of 1:50 and a temperature of 25℃,
After washing with water, it was air-dried. The dyes used were Leverfix Navy Blue E-2R, Leverfix Golden Yellow E-G, manufactured by ICI, Mikasion Brilliant Blue RS, manufactured by Nippon Kayaku, and Drimalene Brilliant Red K-4BL, manufactured by Sandoz. Example 5 Cotton gear dyed with a reactive dye was treated analogously to Example 4 using the composition obtained in Example 2. Example 6 Cotton gear dyed with a reactive dye was treated in the same manner as in Example 4, except that the composition obtained in Example 3 was used. Example 7 The composition obtained in Example 1 was treated in the same manner as in Example 4, except that the temperature was changed to 50° C., to treat cotton gear dyed with a reactive dye. EXAMPLE 8 The composition obtained in Example 2 was treated with cotton gear dyed with a reactive dye in the same manner as in Example 4, except that the temperature was 5° C. and the metal salt was changed to aluminum sulfate. In addition, the hue of the cotton giaba treated in Examples 1 to 3 was almost the same as that of the untreated product. Reference Example 1 Cotton Gyaba dyed with the same reactive dye as in Example 4 was treated with tara tannin at a treatment amount of 2% (ow
f.), immersion treatment was carried out for 20 minutes at a bath ratio of 1:50, pH 5, and temperature of 25°C. Subsequently, after washing with water, the treated cotton gear bar was treated with tartar stone at a treatment amount of 0.6% (OWF) and a bath ratio of 1:
50, PH5, temperature 25℃ for 20 minutes, and after washing with water,
Air dried. Reference Example 2 Cotton gear dyed with the same reactive dye as in Example 4 was dyed using beef tallow alkylpropylene diamine, treatment amount 2% (OWF), bath ratio 1:50, PH5,
It was immersed for 20 minutes at a temperature of 25°C, washed with water, and air-dried. Reference Example 3 Cotton gear dyed with the same reactive dye as in Example 4 was dyed using the composition obtained in Example 1, treatment amount 2% (OWF), bath ratio 1:50, PH5, temperature 25 ℃
After soaking in water for 20 minutes, washing with water, and air drying. Example 9 The following color fastness test was conducted on the treated cotton gear bars obtained in Examples 4 to 8 and Reference Examples 1 to 3. Chlorine fastness test (1) A test piece was immersed in a pH8 buffer solution containing 50 ppm of available chlorine at a bath ratio of 1:100, and after stirring at 25°C for 2 hours,
Washed with water and dried. JIS-
10 of L-0801. The results are shown in the table below. Chlorine fastness test (2) A test piece was immersed in a 50°C aqueous solution of 3 g of commercially available oxygen bleach-containing detergent (product name "Kao Poppins") at a bath ratio of 1:100, and stirred at 50°C for 30 minutes. After washing with water six times, the procedure described in chlorine fastness test (1) was carried out. The judgment of the results in this test was also based on JIS-L-0801 10. The results are shown in the table below. Acid hydrolysis fastness test The test piece and attached white cloth (cotton) were immersed in an aqueous solution containing 10 g of lactic acid at a bath ratio of 1:100, stirred at 60°C for 20 minutes, washed with water, and dried. The determination of contamination of the attached white cloth in this test was based on JIS-L-0801 10. The results are shown in the table below. As is clear from the results, the chlorine fastness of the tannin-metal salt treated fabric is not significantly improved compared to the untreated fabric, whereas the chlorine fastness of the fabric treated with the composition of the present invention is markedly improved. Furthermore, the composition-metal salt-treated fabric of the present invention has a long-lasting effect. Furthermore, in the case of alkylpropylene diamine treatment alone, an improvement in fastness to acid hydrolysis is observed, but no significant improvement in fastness to chlorine is observed.

【表】【table】

【table】

Claims

[Claims] 1 Alkylpropylene diamine represented by R-NHCH ₂ CH ₂ CH ₂ NH ₂ (wherein R is a higher alkyl group) and hydrolyzable tannin in a weight ratio of 1:0.3 to 9.
1. A composition used for improving the chlorine fastness of cotton textile products dyed with a reactive dye, which is characterized by being mixed with a reactive dye. 2 Cotton fiber products dyed with reactive dyes are R-
Treated with a composition obtained by mixing an alkylpropylene diamine represented by NHCH ₂ CH ₂ CH ₂ NH ₂ (wherein R is a higher alkyl group) and a hydrolyzable tannin at a weight ratio of 1:0.3 to 9. A method for improving the chlorine fastness of textile products, which comprises treating with a metal salt.