JP4624542B2 - Dyeing method for wholly aromatic polyamide fiber - Google Patents

Description

【００１２】
【発明の実施の形態】
本発明におけるアラミド繊維とは、アミド結合が芳香族に直結した全芳香族ポリアミドを主たる構成成分とするもので、例えば下記モノマーを組み合わせて重縮合することにより得られるポリマーを言う。
（１）芳香族多価アミンと芳香族多価カルボン酸ハライド
（２）芳香族多価アミンと芳香族多価カルボン酸エステル
（３）芳香族多価アミンと芳香族多価カルボン酸
（４）芳香族多価イソシアネートと芳香族多価カルボン酸
【００１３】
具体的には、メタフェニンレンジアミンとイソフタル酸クロライドとを低温溶液重合或いは、界面重合して得たポリメタフェニレンイソフタルアミドを主成分とするメタ−メタ結合のアラミド繊維（例えば、帝人(株)製コーネックスなど）が好ましく例示され、中でも、特開平８−８１８２７号公報に開示された、メタ系アラミド繊維にアルキルベンゼンスルホン酸オニウム塩が含有されてなる易染性メタ系アラミド繊維を用いれば、本発明の効果がより顕著に発現するので好適である。
【００１４】
かかるアルキルベンゼンスルホン酸オニウム塩としては、ドデシルベンゼンスルホン酸テトラブチルホスホニウム塩の他、下記式に示すドデシルベンゼンスルホン酸トリブチルベンジルアンモニウム塩等を好ましいものとして挙げることができる。
【００１５】
【化３】

【００１６】
つまり、前述のように、アルキルベンゼンスルホン酸オニウム塩を含有するメタ系アラミド繊維は、防炎性が阻害されるという問題が発生するため、通常、下記式で示されるハロゲン化燐酸エステル系難燃剤等の難燃剤を同時に含有させる。
【００１７】
【化４】

【００１８】
ここで、ハロゲン化燐酸エステル中のＲは炭素数２〜６、好ましくは炭素数２〜３のハロゲン化アルキル基を表すが、ハロゲン原子は塩素又は臭素を示し、ハロゲン化アルキル基中のハロゲンの置換数は１でも２以上であってもよい。中でも、２−クロロエチル基、２−クロロプロピル基が、抗菌性、難燃性及び洗濯耐久性をより高レベルにする効果が期待出来るので好ましい。Ｘは直接結合又は炭素数１〜４のアルキレン基を表す。また、ｎは０〜１０の整数であり、なかでも特に２〜４の範囲の整数が好ましい。
【００１９】
ところが、上記のような難燃剤は、染色時に染液中にブリードアウトし易く、せっかく難燃剤を含有させても染色後は脱落してしまうので、充分な難燃性を付与することができなかった。
【００２０】
本発明者らは、この難燃剤のブリードアウト現象について鋭意検討した結果、上記のような難燃剤を含むアラミド繊維を染色する際、下記式で表される燐系化合物を染色助剤として染液中に存在させるとき、難燃剤のブリードアウトが抑制されて、染色後のアラミド繊維に充分な難燃性を付与できることを究明した。
【００２１】
【化５】

【００２２】
中でも、Ｒの炭素原子数が４である場合に本発明の効果が顕著に発現し、具体的にはトリイソブチルホスファートを最も好ましいものとして挙げることが出来る。
【００２３】
即ち、易染剤であるアルキルベンゼンスルホン酸オニウム塩と、ハロゲン化燐酸エステル系難燃剤等の難燃剤とを含有するメタ系アラミド繊維を染色するに際し、上記の燐系化合物を染色助剤として染液中に存在させれば、難燃剤の脱落が防止され、従来は両立が不可能であった、染色性と難燃性という相反する性質が共に良好なメタ系アラミド繊維が得られるのである。
【００２４】
この際、燐系化合物をイソプロパノール中に分散させた状態で使用すると、本発明の効果がさらに顕著になる上、染色時の消泡効果も奏される。
【００２５】
この理由の詳細は不明であるが、イソプロパノールが繊維間空隙への浸透剤として寄与すると共に、消泡効果も併せ持つためであると思われる。
【００２６】
上記燐系化合物の染色助剤としての使用量は、０．１〜１ｍｌ／ｌの範囲が好ましく、０．２〜０．５ｍｌ／ｌの範囲が特に好ましい。該使用量が０．１ｍｌ／ｌ未満では、本発明の効果が充分に奏されない場合があり、一方、該使用量が１ｍｌ／ｌを超えると、染色機（通常は液流染色機）が缶体汚染される場合がある。
【００２７】
また、染色温度は、１１０℃以上１５０℃以下が好ましく１２０℃以上がより好ましい。染色温度が１１０℃未満の場合は、アラミド繊維の染色性が不十分になる場合がある。染色温度は高いほど染色性（染着性）が高まるものの、染料の分解や、アラミド繊維と他の素材を複合している場合には他の素材の劣化の問題が発生することもあるので、必ずしも高温にすればするほど良いわけではなく、高々１４０℃程度であることが好ましい。
【００２８】
上記アラミド繊維を染色するに際しては、繊維の状態で染色しても構わないし、該繊維を紡績糸条、長繊維糸条、ロープ、織編物或いは不織布などの繊維構造体に成形した後、染色しても構わない。
【００２９】
また、繊維構造体に成形する際には、アラミド繊維と他の繊維とを混紡、混繊、交織編或いは混綿することもできる。
【００３０】
アラミド繊維に混合する他の繊維素材には特に限定はないが、アラミド繊維の防炎性（難燃性）を生かす上では難燃レーヨン、難燃加工綿、難燃ポリエステル、難燃ビニロンなどの難燃素材が好ましい。
【００３１】
更に、上記アラミド繊維には、本発明の目的を損なわない範囲内で紫外線吸収剤、安定剤、酸化防止剤、帯電防止剤、蛍光増白剤、触媒、着色剤、無機微粒子などを添加しても良い。
【００３２】
上記アラミド繊維を染色する際に使用する染料は、カチオン染料が好ましい。ここで、カチオン染料とは水に可溶性で、塩基性を示す基を有する水溶性染料をいい、アクリル繊維、天然繊維或いはカチオン可染型ポリエステル繊維等の染色に多く用いられているもので、具体的にはジ及びトリアクリルメタン系、キノンイミン（アジン、オキサジン、チアジン）系、キサンテン系、メチン系（ポリメチン、アザメチン）、複素環アゾ系（チアゾールアゾ、トリアゾールアゾ、ベンゾチアゾールアゾ）、アントラキノン系などのカチオン染料がある。また、最近では塩基性基を封鎖することにより水分散型にしたカチオン染料もあるが、両者とも用いることが出来る。
【００３３】
【実施例】
以下、実施例により本発明を更に詳細に説明する。尚、実施例中に記載の被染色物の評価は下記の方法に従って行った。
【００３４】
（１）染色性
マクベス カラーアイ(Macbeth COLOR-EYE)モデルＣＥ−３１００を用いて測定を行い、明度指数Ｌ＊で表現した。明度指数Ｌ＊は、ＪＩＳ Ｚ ８７０１（２度視野ＸＹＺ系による色の表示方法）又はＪＩＳ Ｚ ８７２８（１０度視野ＸＹＺ系による色の表示方法）に規定する三刺激値のＹを用いて、次式より求められるものである。
【００３５】
【数１】

【００３６】
明度指数Ｌ＊は数値が小さいほど濃染化されていることを示す。
【００３７】
（２）防炎性（難燃性）
ＪＩＳ Ｋ ７２０１に準拠し、ＬＯＩ(限界酸素指数)で表した。ＬＯＩ≧２７の場合、防炎性（難燃性）に優れていると言われている。
【００３８】
（３）繊維中の難燃剤含有量
(株)リガク製蛍光Ｘ線分析装置を用い、濃度既知の縮合型ハロゲン化燐酸エステルの標準サンプルから検量線を作成して、繊維中の燐原子の濃度を求めた。この燐原子が総て縮合型ハロゲン化燐酸エステルに由来するものとして、難燃剤の含有量を換算計算して求めた。また、次式により難燃剤保持率を算出し、ブリードアウト抑制効果の指標とした。
【００３９】
【数２】

【００４０】
［実施例１］
ＩＶ１．３５ｄｌ／ｇのポリ−ｍ−フェニレンイソフタルアミド３０ｇをＮ−メチル−２−ピロリドン１１０ｇに溶解し、さらに３．６ｇのドデシルベンゼンスルフォン酸トリブチルベンジルアンモニウム塩と１．０ｇのトリス（βクロロプロピル）ホスフェートとを混合溶解し、減圧脱泡して紡糸ドープとした。
【００４１】
このドープを８５℃に加温し、口径０．０７ミリ、孔数２００の紡糸口金から凝固浴中に湿式紡糸した。凝固浴の組成は、塩化カルシウムが４０重量％、ＮＭＰが５重量％、水が５５重量％であり、凝固浴の温度は８５℃であった。
【００４２】
この凝固浴中に紡出糸条を約１０ｃｍ走行させ６．２ｍ／分の速度で引き出した。該糸条を水洗し、９５℃の温水で３．５倍に延伸して１２０℃ロールで乾燥した後、２８０℃の熱板上で１．１倍に延伸して、４４４ｄｔｅｘ／２００フィラメントの延伸糸を得た。全延伸倍率は３．５倍であった。該延伸糸から常法により紡績糸を得、次いで該紡績糸を製織して平織物（密度：経４２本／ｉｎ、緯４６本／ｉｎ）を得た。
【００４３】
得られた織物を１ｇ／ｌのスコアロール＃４００（花王製）で、８０℃で２０分間精練し、水洗・乾燥後、１９０℃で１分間プレ・セットした。次いで、下記染浴で常温から２℃／分の速度で昇温し、１３５℃で６０分間染色した。
・染料 C.I.Basic Blue 54(Kayacryl Blue GSL-ED(日本化薬製) ４ %owf
・硝酸Ｎａ ２５ g/l
・酢酸 ０．５ ｃｃ／ｌ
・染色助剤 （トリイソブチルホスファート） ０．５ ｃｃ／ｌ
・浴比 １：３０
【００４４】
染色後、染色布帛を取り出し、次いで、染色された試料を下記洗浄浴で８０℃×２０分間還元洗浄した。
・ＮａＯＨ １ｇ／ｌ
・ハイドロサルファイト １ｇ／ｌ
・アミラジンＤ （第一工業製薬製、非イオン活性剤） １ｇ／ｌ
還元洗浄後、十分水洗して乾燥、ファイナル・セット（１８０℃×１分間）した。結果を表１に示す。
【００４５】
［実施例２］
実施例１において、染色助剤であるトリイソブチルホスファートをイソプロパノール中に分散させた状態で使用した以外は、実施例１と同様に実施した。結果を表１に示す。
【００４６】
［比較例１］
実施例１において、染色助剤であるトリイソブチルホスファートを使用しなかった以外は、実施例１と同様に実施した。結果を表１に示す。
【００４７】
［比較例２］
実施例１において、トリイソブチルホスファートに代えてシリコン系の染色助剤（消泡剤）を使用した以外は実施例１と同様に実施した。結果を表１に示す。
【００４８】
【表１】

【００４９】
【発明の効果】
本発明によれば、難燃剤の染色液中へのブリードアウトが抑制され、染色性と難燃性という相反する性質が共に良好なアラミド繊維、就中メタ系アラミド繊維が得られる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for dyeing a wholly aromatic polyamide fiber containing a flame retardant, and more specifically, when dyeing a wholly aromatic polyamide fiber containing a flame retardant, a phosphorus compound is used in combination as a dyeing aid. Thus, the present invention relates to a method for dyeing wholly aromatic polyamide fibers, which can prevent a reduction in flame retardancy.
[0002]
[Prior art]
The fully aromatic polyamide (hereinafter abbreviated as aramid) fibers include meta-aramid fibers represented by Conex and Nomex, and para-aramid fibers represented by Technora, Kevlar and Twaron.
[0003]
These aramid fibers are heat resistant and flame resistant (flame retardant) due to their rigid molecular structure and high crystallinity compared to the widely used aliphatic polyamide fibers such as nylon 6 and nylon 66. As well as excellent thermal properties such as chemical resistance, strong radiation resistance, and electrical properties. Therefore, it is widely used for industrial materials such as bag filters, interiors such as curtains, and clothing such as protective clothing that requires flame resistance (flame resistance) and heat resistance.
[0004]
In addition, fire retardants have been using non-combustible asbestos fibers and glass fibers for fire extinguishing work. However, in recent years, aramid fibers have been used from the viewpoint of environmental issues and ease of movement. In particular, meta-aramid fibers are preferably used when flame resistance is important.
[0005]
However, the meta-aramid fiber has a drawback that it is difficult to dye in post-processing because the molecular chain is rigid and highly crystalline. To solve this, after pre-treatment with a polar solvent or carrier Although a method for dyeing has been proposed, the method has a problem such as a worsening working environment and has not yet been put into practical use.
[0006]
On the other hand, JP-A-8-81827 discloses a method for improving the dyeability of meta-aramid fibers by adding an alkyl benzene sulfonic acid onium salt.
[0007]
However, when an alkylbenzene sulfonic acid onium salt is included in the meta-aramid fiber, there is a problem that the flame resistance, which is the greatest feature of the meta-aramid fiber, is impaired. Although a flame retardant is contained at the same time, in general, a flame retardant tends to bleed out in a dyeing solution, and thus there has been a problem that a dyed meta-aramid fiber does not exhibit a sufficient flame retardancy imparting effect.
[0008]
[Problems to be solved by the invention]
An object of the present invention is to solve the above-mentioned problems of the prior art and to provide a method for dyeing aramid fibers, especially meta-aramid fibers, which have good conflicting properties such as dyeability and flame retardancy.
[0009]
[Means for Solving the Problems]
As a result of diligent investigations to achieve the above object, the present inventors have found that when dyeing an aramid fiber containing a flame retardant, when using a phosphorus compound having a specific structure as a dyeing assistant, the effect of adding the flame retardant Investigated that can be maximized.
[0010]
Thus, according to the present invention, when dyeing a wholly aromatic polyamide fiber containing a flame retardant, the phosphorous compound represented by the following formula (I) is used in combination as a dyeing assistant, and the dyeing of wholly aromatic polyamide fiber is characterized in that A method is provided.
[0011]
[Chemical 2]

[0012]
DETAILED DESCRIPTION OF THE INVENTION
The aramid fiber in the present invention is mainly composed of a wholly aromatic polyamide in which an amide bond is directly bonded to an aromatic, and refers to a polymer obtained by polycondensation by combining the following monomers, for example.
(1) Aromatic polyvalent amine and aromatic polyvalent carboxylic acid halide (2) Aromatic polyvalent amine and aromatic polyvalent carboxylic acid ester (3) Aromatic polyvalent amine and aromatic polyvalent carboxylic acid (4) Aromatic polyvalent isocyanate and aromatic polycarboxylic acid
Specifically, a meta-meta bond aramid fiber (for example, Teijin Ltd.) mainly composed of polymetaphenylene isophthalamide obtained by low temperature solution polymerization or interfacial polymerization of metaphenylene diamine and isophthalic acid chloride. ) Manufactured by Conex, etc.) is preferred, and among them, if an easily dyeable meta-aramid fiber, which is disclosed in JP-A-8-81827, and contains an alkylbenzene sulfonic acid onium salt in a meta-aramid fiber, is used. This is preferable because the effects of the present invention are more remarkably exhibited.
[0014]
Preferred examples of the alkylbenzenesulfonic acid onium salt include dodecylbenzenesulfonic acid tetrabutylphosphonium salt, dodecylbenzenesulfonic acid tributylbenzylammonium salt represented by the following formula, and the like.
[0015]
[Chemical 3]

[0016]
That is, as described above, the meta-aramid fiber containing an alkylbenzene sulfonic acid onium salt has a problem in that the flameproofness is hindered. Therefore, usually, a halogenated phosphate ester flame retardant represented by the following formula, etc. These flame retardants are simultaneously contained.
[0017]
[Formula 4]

[0018]
Here, R in the halogenated phosphoric acid ester represents a halogenated alkyl group having 2 to 6 carbon atoms, preferably 2 to 3 carbon atoms, and the halogen atom represents chlorine or bromine. The number of substitutions may be 1 or 2 or more. Among these, a 2-chloroethyl group and a 2-chloropropyl group are preferable because the antibacterial property, flame retardancy, and washing durability can be expected to have a higher level. X represents a direct bond or an alkylene group having 1 to 4 carbon atoms. N is an integer of 0 to 10, and an integer in the range of 2 to 4 is particularly preferable.
[0019]
However, flame retardants such as those mentioned above tend to bleed out in the dyeing solution at the time of dyeing, and even if they contain a flame retardant, they will fall off after dyeing, so that sufficient flame retardancy cannot be imparted. It was.
[0020]
As a result of intensive studies on the bleed-out phenomenon of this flame retardant, the present inventors have used a phosphorus compound represented by the following formula as a dyeing assistant when dyeing an aramid fiber containing the above flame retardant. It has been clarified that when it is present in the inside, the bleed-out of the flame retardant is suppressed and sufficient flame retardancy can be imparted to the aramid fiber after dyeing.
[0021]
[Chemical formula 5]

[0022]
Among them, when the number of carbon atoms in R is 4, the effects of the present invention are remarkably exhibited, and specifically, triisobutyl phosphate can be mentioned as the most preferable one.
[0023]
That is, when dyeing a meta-aramid fiber containing an alkylbenzene sulfonic acid onium salt that is an easy dye and a flame retardant such as a halogenated phosphate ester flame retardant, the above-described phosphorus compound is used as a dyeing assistant as a dyeing solution. If present in the medium, the flame retardant is prevented from falling off, and a meta-aramid fiber having both contradictory properties of dyeability and flame retardance, both of which have been impossible in the past, is obtained.
[0024]
At this time, if the phosphorous compound is used in a state of being dispersed in isopropanol, the effect of the present invention becomes more remarkable, and an antifoaming effect at the time of dyeing is also exhibited.
[0025]
Although the details of this reason are unknown, it is thought that isopropanol contributes as a penetrant to the inter-fiber voids and also has an antifoaming effect.
[0026]
The amount of the phosphorus compound used as a dyeing assistant is preferably in the range of 0.1 to 1 ml / l, particularly preferably in the range of 0.2 to 0.5 ml / l. If the amount used is less than 0.1 ml / l, the effect of the present invention may not be sufficiently achieved. On the other hand, if the amount used exceeds 1 ml / l, the dyeing machine (usually a liquid dyeing machine) can be used. May be contaminated.
[0027]
The dyeing temperature is preferably 110 ° C. or higher and 150 ° C. or lower, and more preferably 120 ° C. or higher. When the dyeing temperature is lower than 110 ° C., the dyeability of the aramid fiber may be insufficient. The higher the dyeing temperature, the higher the dyeability (dyeability). However, if the dye is decomposed or aramid fiber and other materials are combined, other materials may deteriorate. The higher the temperature, the better. It is preferably at most about 140 ° C.
[0028]
When the aramid fiber is dyed, it may be dyed in a fiber state, and the fiber is molded into a fiber structure such as a spun yarn, a long fiber yarn, a rope, a woven or knitted fabric, and then dyed. It doesn't matter.
[0029]
Further, when forming into a fiber structure, aramid fibers and other fibers can be blended, blended, interwoven, or blended.
[0030]
Other fiber materials to be mixed with aramid fiber are not particularly limited. However, flame retardant rayon, flame retardant processed cotton, flame retardant polyester, flame retardant vinylon, etc. Flame retardant materials are preferred.
[0031]
Further, the aramid fiber is added with an ultraviolet absorber, a stabilizer, an antioxidant, an antistatic agent, an optical brightener, a catalyst, a colorant, inorganic fine particles, etc. within a range not impairing the object of the present invention. Also good.
[0032]
The dye used when dyeing the aramid fiber is preferably a cationic dye. Here, the cationic dye is a water-soluble dye having a basic group that is soluble in water, and is often used for dyeing acrylic fiber, natural fiber, or cationic dyeable polyester fiber. Specifically, di- and triacrylmethane, quinoneimine (azine, oxazine, thiazine), xanthene, methine (polymethine, azamethine), heterocyclic azo (thiazoleazo, triazoleazo, benzothiazoleazo), anthraquinone, etc. There is a cationic dye. Recently, there is a cationic dye which is made water-dispersible by blocking a basic group, but both can be used.
[0033]
【Example】
Hereinafter, the present invention will be described in more detail with reference to examples. In addition, evaluation of the to-be-dyed object as described in an Example was performed in accordance with the following method.
[0034]
(1) Dyeability Macbeth Color-eye (Macbeth COLOR-EYE) Model CE-3100 was used for measurement, and the brightness index L * was expressed. The lightness index L * is determined by using Y of the tristimulus value specified in JIS Z 8701 (color display method by 2 degree visual field XYZ system) or JIS Z 8728 (color display method by 10 degree visual field XYZ system). It is obtained from the formula.
[0035]
[Expression 1]

[0036]
The lightness index L * indicates that the smaller the value, the deeper the dyeing.
[0037]
(2) Flame resistance (flame retardant)
Based on JIS K 7201, it was expressed as LOI (Limited Oxygen Index). When LOI ≧ 27, it is said to be excellent in flameproofing (flame retardant).
[0038]
(3) Flame retardant content in fiber
Using a fluorescent X-ray analyzer manufactured by Rigaku Corporation, a calibration curve was prepared from a standard sample of a condensed halogenated phosphate having a known concentration, and the concentration of phosphorus atoms in the fiber was determined. Assuming that all of these phosphorus atoms are derived from the condensed halogenated phosphate ester, the content of the flame retardant was calculated by conversion. Moreover, the flame retardant retention rate was calculated by the following formula and used as an index of the bleed-out suppression effect.
[0039]
[Expression 2]

[0040]
[Example 1]
30 g of 1.35 dl / g poly-m-phenylene isophthalamide was dissolved in 110 g of N-methyl-2-pyrrolidone, and 3.6 g of tributylbenzylammonium dodecylbenzenesulfonate and 1.0 g of tris (β-chloropropyl) were added. ) Phosphate was mixed and dissolved, and defoamed under reduced pressure to obtain a spinning dope.
[0041]
This dope was heated to 85 ° C. and wet-spun into a coagulation bath from a spinneret having a diameter of 0.07 mm and a hole number of 200. The composition of the coagulation bath was 40% by weight of calcium chloride, 5% by weight of NMP and 55% by weight of water, and the temperature of the coagulation bath was 85 ° C.
[0042]
In this coagulation bath, the spun yarn was run about 10 cm and pulled out at a speed of 6.2 m / min. The yarn is washed with water, stretched 3.5 times with warm water at 95 ° C., dried with a roll at 120 ° C., stretched 1.1 times on a hot plate at 280 ° C., and stretched at 444 dtex / 200 filament. I got a thread. The total draw ratio was 3.5 times. A spun yarn was obtained from the drawn yarn by a conventional method, and then the spun yarn was woven to obtain a plain fabric (density: warp 42 / in, weft 46 / in).
[0043]
The obtained woven fabric was scoured at 80 ° C. for 20 minutes with 1 g / l score roll # 400 (manufactured by Kao), washed and dried, and then pre-set at 190 ° C. for 1 minute. Next, the temperature was increased from room temperature at a rate of 2 ° C./minute in the following dye bath, and dyeing was performed at 135 ° C. for 60 minutes.
・ Dye CIBasic Blue 54 (Kayacryl Blue GSL-ED (Nippon Kayaku) 4% owf
・ Na nitrate 25 g / l
・ Acetic acid 0.5 cc / l
・ Dyeing assistant (triisobutyl phosphate) 0.5 cc / l
・ Bath ratio 1:30
[0044]
After dyeing, the dyed fabric was taken out, and then the dyed sample was reduced and washed in the following washing bath at 80 ° C. for 20 minutes.
・ NaOH 1g / l
・ Hydrosulfite 1g / l
Amylazine D (Daiichi Kogyo Seiyaku, nonionic active agent) 1 g / l
After the reduction cleaning, it was washed thoroughly with water, dried and final set (180 ° C. × 1 minute). The results are shown in Table 1.
[0045]
[Example 2]
In Example 1, it carried out similarly to Example 1 except having used the triisobutyl phosphate which is a dyeing assistant in the state disperse | distributed in isopropanol. The results are shown in Table 1.
[0046]
[Comparative Example 1]
In Example 1, it carried out like Example 1 except not having used triisobutyl phosphate which is a dyeing assistant. The results are shown in Table 1.
[0047]
[Comparative Example 2]
In Example 1, it carried out similarly to Example 1 except having replaced with the triisobutyl phosphate and using the silicon-type dyeing assistant (antifoamer). The results are shown in Table 1.
[0048]
[Table 1]

[0049]
【The invention's effect】
According to the present invention, the bleed-out of the flame retardant into the dyeing liquid is suppressed, and an aramid fiber, especially a meta-aramid fiber, which has good conflicting properties of dyeability and flame retardancy can be obtained.

Claims (7)

A dyeing method for a wholly aromatic polyamide fiber, which comprises using a phosphorus compound represented by the following formula (I) as a dyeing auxiliary when dyeing a wholly aromatic polyamide fiber containing a flame retardant.

The method for dyeing wholly aromatic polyamide fibers according to claim 1, wherein the phosphorus compound is dispersed in isopropanol. The method for dyeing a wholly aromatic polyamide fiber according to claim 1 or 2, wherein the wholly aromatic polyamide fiber is a wholly aromatic polyamide fiber containing an alkylbenzenesulfonic acid onium salt. The method for dyeing wholly aromatic polyamide fibers according to claim 1, 2 or 3, wherein the flame retardant is a phosphate ester and / or a condensed phosphate ester flame retardant. The method for dyeing a wholly aromatic polyamide fiber according to any one of claims 1 to 4, wherein the wholly aromatic polyamide fiber is a meta-aromatic polyamide fiber. The dyeing | staining temperature is 110 degreeC or more, The dyeing | staining method of the fully aromatic polyamide fiber of any one of Claims 1-5. The method for dyeing wholly aromatic polyamide fibers according to any one of claims 1 to 6, wherein the dye used for dyeing is a cationic dye.