JP2000328357A - Production of heat-resistant polyamide-based fiber - Google Patents
Production of heat-resistant polyamide-based fiberInfo
- Publication number
- JP2000328357A JP2000328357A JP11140594A JP14059499A JP2000328357A JP 2000328357 A JP2000328357 A JP 2000328357A JP 11140594 A JP11140594 A JP 11140594A JP 14059499 A JP14059499 A JP 14059499A JP 2000328357 A JP2000328357 A JP 2000328357A
- Authority
- JP
- Japan
- Prior art keywords
- polyamide
- antioxidant
- heat
- dyeability
- fibers
- 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
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術】本発明は耐熱性に優れ、染色品の
品位を向上することができるポリアミド系繊維の製造方
法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a polyamide fiber which has excellent heat resistance and can improve the quality of a dyed product.
【０００２】[0002]
【従来の技術】ポリアミド系繊維は種々の優れた特性を
有するので、織編物等の布帛として広く利用されてい
る。ポリアミド系繊維製品では染色加工前に布帛形態を
安定化するために、１３０〜２１０℃の温度で３０秒〜
３分間の乾熱処理が行われている。しかし、この熱処理
によって染色斑および染色筋が発生する問題が生じ易
い。つまり、熱処理バラツキにより染色性が低下した
り、染色斑や染色筋が発生する。2. Description of the Related Art Polyamide fibers have various excellent properties and are therefore widely used as woven or knitted fabrics. In the case of polyamide-based fiber products, in order to stabilize the fabric form before dyeing, the temperature is 130 to 210 ° C for 30 seconds.
Dry heat treatment is performed for 3 minutes. However, this heat treatment tends to cause a problem that stained spots and stained streaks are generated. That is, the stainability is reduced due to the variation in the heat treatment, and stained spots and stained streaks are generated.
【０００３】これは、ポリアミド系繊維製品の布帛形態
安定化の為の熱処理により、ポリアミド系繊維のアミノ
末端基が減少して、酸性染料が染着されにくくなる為と
思われる。つまり、Ties Karstensらの報文Makromol.C
hem.No.191(1990)に掲載されているように、ポリアミド
分子中のアミノ末端基が高温加熱によって減少すること
やポリマー主鎖中のアミド結合が切断されアルデヒドお
よびケトンカルボニル基が生成し、これがアミノ基と反
応し黄色の色原体を形成することが知られている。前記
の熱によるアミノ末端基の減少および熱黄変はともにア
ミノ末端基が消費され、酸性染料の染着座席の減少を生
じ、結果として染色性が低下する。This is presumably because the heat treatment for stabilizing the fabric form of the polyamide fiber product reduces the amino terminal groups of the polyamide fiber and makes it difficult for the acid dye to be dyed. In other words, the report Makromol.C of Ties Karstens et al.
As described in hem. No. 191 (1990), the amino terminal group in the polyamide molecule is reduced by heating at a high temperature, the amide bond in the polymer main chain is cleaved, and aldehyde and ketone carbonyl groups are generated, It is known that this reacts with an amino group to form a yellow chromogen. Both the heat-induced reduction of the amino terminal groups and the heat yellowing consume the amino terminal groups, resulting in a reduction in the number of dyeing sites for the acid dyes and consequently the dyeability is reduced.
【０００４】かかる熱酸化劣化によるポリアミド系繊維
のアミノ末端基の減少や黄変を防ぐ方法として、通常の
ヒンダードフェノール系もしくは、ヒンダードアミン
系、セミカルバジド系化合物等の酸化防止剤を、重合時
もしくは染色加工段階（特に高温乾熱処理前）で添加す
る方法が知られているが、これらの方法であればアミノ
末端基の減少を抑え、黄変を防ぎ、結果として染色性向
上に有効であるが、前者の重合時添加方法では、原糸自
身が着色したり、最終製品で残存する酸化防止剤に起因
する各種黄変トラブル、例えば、ＮＯｘガス、プロパン
燃焼ガス等のガス黄変や光、熱での酸化防止剤自身の黄
変が問題となる場合があり、後者の染色加工段階で添加
する方法では、後加工工程が増えて効率的生産には不向
きである等の問題があった。As a method for preventing the reduction or yellowing of the amino terminal group of the polyamide fiber due to the thermal oxidation deterioration, a conventional antioxidant such as a hindered phenol-based, hindered amine-based or semicarbazide-based compound is used during polymerization or dyeing. Methods of adding at the processing stage (especially before high-temperature dry heat treatment) are known, but these methods are effective in suppressing the decrease in amino terminal groups, preventing yellowing, and as a result, improving dyeability. In the former addition method at the time of polymerization, the yarn itself is colored or various yellowing troubles caused by the antioxidant remaining in the final product, for example, gas yellowing such as NOx gas, propane combustion gas, light, heat, etc. The yellowing of the antioxidant itself may be a problem, and the latter method of adding at the dyeing stage has a problem that the number of post-processing steps increases and is not suitable for efficient production. Was Tsu.
【０００５】また、熱黄変を防ぐ方法として、熱処理温
度を下げたり、処理時間を短くする方法があるが、これ
らの方法は染色性向上には有効であるが、ポリアミド系
繊維製品の染色時の端部の丸まりやロープマークと呼ば
れる皺ができる等、布帛形態の安定性が悪くなり、染色
性と布帛形態安定性両方を満足するものはいまだ得られ
ていない。As a method for preventing thermal yellowing, there are methods of lowering the heat treatment temperature and shortening the treatment time. These methods are effective for improving the dyeing property, but they are not effective for dyeing polyamide fiber products. , The stability of the fabric form is deteriorated, such as rounding of the ends and wrinkles called rope marks, and there is still no product that satisfies both the dyeability and the fabric form stability.
【０００６】[0006]
【発明が解決しようとする課題】本発明は、耐熱性に優
れ、また均染性に優れたポリアミド系繊維を効率的に製
造する方法を提供することを目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for efficiently producing a polyamide fiber having excellent heat resistance and excellent levelness.
【０００７】[0007]
【課題を解決するための手段】本発明は、ポリアミド繊
維を溶融紡糸後、ポリマーが固化した以降で未延伸糸に
紡糸油剤を付与して捲き取る以前に、酸化防止剤を付与
することを特徴とする耐熱性ポリアミド系繊維の製造方
法である。また、酸化防止剤が下記化合物のうちの１種
以上である耐熱性ポリアミド系繊維の製造方法である。 １）ヒンダードアミン系化合物 ２）ヒンダードフェノール系化合物 ３）セミカルバジド系化合物According to the present invention, an antioxidant is added after melt-spinning a polyamide fiber and before applying a spinning oil to an undrawn yarn after the polymer is solidified and winding it up. Is a method for producing a heat-resistant polyamide fiber. Further, the present invention relates to a method for producing a heat-resistant polyamide fiber in which the antioxidant is at least one of the following compounds. 1) Hindered amine compounds 2) Hindered phenol compounds 3) Semicarbazide compounds
【０００８】[0008]
【発明の実施の形態】以下に、本発明を詳細に説明す
る。本発明におけるポリアミド系繊維とは、ナイロン−
６、ナイロン−６，６、ナイロン−４，６およびポリア
ミド／ポリエステル複合繊維等の合成繊維であり、好ま
しくはナイロン−６を用いることができる。また、紡糸
方法としては、通常の溶融方式が適用される。また、ポ
リアミドポリマーは、通常添加される添加剤、例えば艶
消剤、安定剤、制電剤等を含んでいてもよい。繊維の断
面形状および繊度は用途に応じて適宜選択される。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The polyamide fiber in the present invention is nylon-
Synthetic fibers such as 6, nylon-6,6, nylon-4,6 and polyamide / polyester composite fiber, and nylon-6 can be preferably used. As a spinning method, an ordinary melting method is applied. Further, the polyamide polymer may contain additives usually added, for example, a matting agent, a stabilizer, an antistatic agent and the like. The cross-sectional shape and fineness of the fiber are appropriately selected depending on the application.
【０００９】本発明における紡糸油剤とは、合成繊維を
製造する際に通常使用されるもであり、鉱物油系、特殊
アニオン系、特殊ノニオン系、特殊カチオン系を用いる
ことができ、用途に応じて適宜選択される。[0009] The spinning oil agent in the present invention is commonly used in the production of synthetic fibers. Mineral oils, special anions, special nonions, and special cations can be used. Selected as appropriate.
【００１０】本発明における酸化防止剤とは、下記に示
されるものの中から１種以上が使用される。 １）ヒンダードアミン系化合物 ２）ヒンダードフェノール系化合物 ３）セミカルバジド系化合物[0010] As the antioxidant in the present invention, one or more of the following are used. 1) Hindered amine compounds 2) Hindered phenol compounds 3) Semicarbazide compounds
【００１１】ヒンダードアミン系化合物としては、特に
限定されるものではないが、例えばコハク酸ジメチル−
1-(2-ヒドロキシエチル)-4-ヒドロキシ-2,2,6,6-テトラ
メチルピペリジン重縮合物やポリ[[6-(1,1,3,3-テトラ
メチルブチル)アミノ-1,3,5-トリアジン-2,4-ジイル]
[(2,2,6,6,-テトラメチル-4-ピペリジル)イミノ]ヘキサ
メチレン[(2,2,6,6,-テトラメチル-4-ピペリジル)イミ
ノ]]やN,N'-ビス(3-アミノプロピル)エチレンジアミン
・2,4-ビス[N-ブチル-N-(1,2,2,6,6-ペンタメチル-4ピ
ペリジル)アミノ]-6-クロロ-1,3,5-トリアジン縮合物な
どがあげられる。The hindered amine compound is not particularly limited, but for example, dimethyl succinate-
1- (2-hydroxyethyl) -4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate or poly [[6- (1,1,3,3-tetramethylbutyl) amino-1, 3,5-triazine-2,4-diyl]
[(2,2,6,6-, tetramethyl-4-piperidyl) imino] hexamethylene [(2,2,6,6, -tetramethyl-4-piperidyl) imino]] and N, N'-bis (3-Aminopropyl) ethylenediamine-2,4-bis [N-butyl-N- (1,2,2,6,6-pentamethyl-4piperidyl) amino] -6-chloro-1,3,5-triazine And condensates.
【００１２】ヒンダードフェノール系化合物としては、
特に限定されるものではないが、例えばトリエチレング
リコール-ビス[3-(3-t-ブチル-5-メチル-4-ヒドロキシ
フェニル)プロピオネート]やペンタエリスリチル-テト
ラキス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プ
ロピオネート]やN,N'-ヘキサメチレンビス(3,5-ジ-t-ブ
チル-4-ヒドロキシ-ヒドロシンナマミド)や3,5-ジ-t-ブ
チル-4-ヒドロキシ-ベンジルフォスフォネート-ジエチ
ルエステルなどがあげられる。The hindered phenol compounds include:
Although not particularly limited, for example, triethylene glycol-bis [3- (3-t-butyl-5-methyl-4-hydroxyphenyl) propionate] and pentaerythrityl-tetrakis [3- (3,5- Di-t-butyl-4-hydroxyphenyl) propionate], N, N'-hexamethylenebis (3,5-di-t-butyl-4-hydroxy-hydrocinnamamide) and 3,5-di-t -Butyl-4-hydroxy-benzylphosphonate-diethyl ester.
【００１３】セミカルバジド系化合物としては、特に限
定されるものではないが、例えば下記一般式（１）： (CH3)2NNHCONH-(CH2)m-NHCONHN(CH3)2 （１） ［式中ｍは１〜１１の整数である］で示され、この中で
好ましいものとしてｍ＝６の化合物等があげられる。The semicarbazide compound is not particularly limited. For example, the following general formula (1): (CH 3 ) 2 NNHCONH- (CH 2 ) m-NHCONHN (CH 3 ) 2 (1) Wherein m is an integer of 1 to 11], and preferred examples thereof include compounds in which m = 6.
【００１４】かかる酸化防止剤の付与量は該繊維に対し
て、０．００１〜５重量％の範囲の中から選択される。
付与量がこの範囲内であれば、原糸着色もなく、また、
経済的に耐熱性の良好なものが得られる。The amount of the antioxidant to be applied is selected from the range of 0.001 to 5% by weight based on the weight of the fiber.
As long as the applied amount is within this range, there is no coloring of the yarn,
Good heat resistance can be obtained economically.
【００１５】具体的な付与方法としては、紡糸後、ポリ
マーが固化した以降で、未延伸糸を捲き取る以前に、酸
化防止剤を付与し、その後紡糸油剤を付与する。一般に
は該酸化防止剤の水溶液あるいは水分散液を油剤付与装
置で付与する。かかる付与方法に比べて、該酸化防止剤
を紡糸油剤付与後あるいは紡糸油剤に混ぜて付与する
と、後工程での処理により酸化防止剤が脱落する場合が
あり、耐熱性が低下することがある。As a specific application method, an antioxidant is applied after spinning and before the undrawn yarn is wound up after the solidification of the polymer, and thereafter a spinning oil agent is applied. Generally, an aqueous solution or aqueous dispersion of the antioxidant is applied by an oil agent application device. If the antioxidant is applied after the spinning oil agent is applied or mixed with the spinning oil agent, the antioxidant may fall off due to the treatment in the subsequent step, and the heat resistance may be reduced as compared with the method of applying the antioxidant.
【００１６】[0016]
【実施例】以下に、本発明の耐熱性ポリアミド系繊維の
製造方法に関する具体例を詳細に説明するが、本発明は
実施例のみに限定されるものではない。実施例における
評価は次の評価方法によった。EXAMPLES Hereinafter, specific examples relating to the method for producing the heat-resistant polyamide fiber of the present invention will be described in detail, but the present invention is not limited to only the examples. The evaluation in the examples was based on the following evaluation method.
【００１７】(1)耐熱性 後述する実施例、比較例のように乾熱処理まで実施した
サンプルの黄変度を目視判定で３段階評価する。 ○；ほとんど黄変しない。 △；やや黄変する。 ×；かなり黄変する。(1) Heat resistance The degree of yellowing of a sample which has been subjected to dry heat treatment as in Examples and Comparative Examples to be described later is evaluated in three stages by visual judgment. ；: Almost no yellowing. Δ: slightly yellowed. X: considerably yellowed.
【００１８】(2)染色性 後述する実施例、比較例のように乾熱処理まで実施した
サンプルをミーリングタイプ・ブルー系酸性染料（品
名：Kayanol Mill. Turq. Blue 3G 1%owf、日本化薬社
製］）で９８℃×３０分酸性染色した後、染色性を目視
判定する。 ○；均一に染まる。 △；やや淡染部分がある。 ×；多数の淡染部分がある。(2) Dyeing properties Samples which had been subjected to dry heat treatment as in Examples and Comparative Examples described later were milled blue acid dyes (product name: Kayanol Mill. Turq. Blue 3G 1% owf, Nippon Kayaku Co., Ltd.). Manufactured) at 98 ° C. for 30 minutes, and then the dyeability is visually determined. ；: Uniform dyeing. Δ: There is a slightly lightly dyed portion. X: There are many lightly dyed portions.
【００１９】(3)寸法安定性 後述する実施例、比較例のように乾熱処理まで実施した
サンプルに１０ｃｍの印をつけて、９８℃、３０分の沸
水処理後の収縮率から評価する。 ○；ほとんど収縮しない。 △；やや収縮する。 ×；かなり収縮する。(3) Dimensional stability Samples which have been subjected to dry heat treatment as in Examples and Comparative Examples described later are marked with a 10 cm mark, and evaluated from the shrinkage after the treatment with boiling water at 98 ° C. for 30 minutes. ；: Almost no shrinkage. Δ: Shrinks slightly. X; considerably shrinks.
【００２０】実施例１ ナイロン−６レジンを通常の溶融紡糸装置を使用して、
溶融紡糸後、未延伸糸にヒンダードアミン系化合物酸化
防止剤；ポリ[[6-(1,1,3,3-テトラメチルブチル)アミノ
-1,3,5-トリアジン-2,4-ジイル][(2,2,6,6,-テトラメチ
ル-4-ピペリジル)イミノ]ヘキサメチレン[(2,2,6,6,-テ
トラメチル-4-ピペリジル)イミノ]]を繊維に対して０．
３重量％付着するように水に１０％分散させた液を油剤
付与装置で付与し、さらに紡糸油剤（主成分が鉱物油、
特殊アニオン系油剤）を繊維に対して１重量％を付与
し、さらに延伸、熱処理後捲き取った。得られた７０デ
ニール２４フィラメントのポリアミド繊維を経糸および
緯糸に用いて、経糸密度２９７本／インチ、緯糸密度１
１０本／インチのタフタ織物を製織した。この織物を常
法により精練後、１９５℃×３分の乾熱処理を実施し
た。得られた布帛の黄変度、染色性、寸法安定性は表１
のようになり、染色性、寸法安定性ともに良好なもので
あった。Example 1 Nylon-6 resin was prepared using a conventional melt spinning apparatus.
After melt-spinning, hindered amine compound antioxidant; poly [[6- (1,1,3,3-tetramethylbutyl) amino
-1,3,5-triazine-2,4-diyl] [(2,2,6,6, -tetramethyl-4-piperidyl) imino] hexamethylene [(2,2,6,6, -tetramethyl -4-piperidyl) imino]] to the fiber.
A solution dispersed in water at 10% so as to adhere to 3% by weight is applied with an oil agent application device, and further, a spinning oil agent (main component is mineral oil,
A special anionic oil agent) was added at 1% by weight to the fiber, stretched, heat-treated, and then wound up. The obtained 70 denier 24-filament polyamide fiber was used for the warp and the weft, and the warp density was 297 yarns / inch and the weft density was 1
Ten / inch taffeta fabrics were woven. After scouring the woven fabric by a conventional method, a dry heat treatment was performed at 195 ° C. for 3 minutes. Table 1 shows the yellowing degree, dyeability and dimensional stability of the obtained fabric.
And both dyeing properties and dimensional stability were good.
【００２１】実施例２ 酸化防止剤をヒンダードフェノール系化合物；N,N'-ヘ
キサメチレンビス(3,5-ジ-t-ブチル-4-ヒドロキシ-ヒド
ロシンナマミド)を繊維に対して０．３重量％を使用し
た以外は実施例１と同様に糸を製造し、布帛を製織し
た。得られた布帛の黄変度、染色性、寸法安定性は表１
のようになり、染色性、寸法安定性ともに良好なもので
あった。Example 2 An antioxidant is a hindered phenol compound; N, N'-hexamethylenebis (3,5-di-t-butyl-4-hydroxy-hydrocinnamamide) is added to the fiber in an amount of 0%. A yarn was produced in the same manner as in Example 1 except that 0.3% by weight was used, and a fabric was woven. Table 1 shows the yellowing degree, dyeability and dimensional stability of the obtained fabric.
And both dyeing properties and dimensional stability were good.
【００２２】実施例３ 酸化防止剤を下記式で示す化合物（ａ）のセミカルバジ
ド系化合物を繊維に対して０．３ｗｔ％を使用した以外
は実施例１と同様に糸を製造し、布帛を製織した。得ら
れた布帛の黄変度、染色性、寸法安定性は表１のように
なり、染色性、寸法安定性ともに良好なものであった。Example 3 A yarn was produced in the same manner as in Example 1 except that 0.3% by weight of a semicarbazide compound represented by the following formula (a) was used as an antioxidant with respect to the fiber, and a fabric was woven. did. The yellowing degree, dyeability and dimensional stability of the obtained fabric were as shown in Table 1, and both the dyeability and the dimensional stability were good.
【００２３】 (CH3)2NNHCONH-(CH2)6-NHCONHN(CH3)2 （ａ） 比較例１ 酸化防止剤を付与しない以外は実施例１と同様に糸を製
造し、布帛を製織し、精練、熱処理を行った。得られた
布帛の黄変度、染色性、寸法安定性は表１のようにな
り、寸法安定性は良好であったが、染色性は品位に欠け
るものであった。(CH 3 ) 2 NNHCONH- (CH 2 ) 6 -NHCONHN (CH 3 ) 2 (a) Comparative Example 1 A yarn was produced in the same manner as in Example 1 except that an antioxidant was not added, and a fabric was woven. Then, scouring and heat treatment were performed. The yellowing degree, dyeability and dimensional stability of the obtained fabric were as shown in Table 1, and the dimensional stability was good, but the dyeability was poor in quality.
【００２４】比較例２ 酸化防止剤を付与しない以外は実施例１と同様に糸を製
造し、布帛を製織した。この織物を常法により精練後、
１８０℃×１分の熱処理を実施した。得られた布帛の黄
変度、染色性、寸法安定性は表１のようになり、染色性
は良好であったが、寸法安定性は品位に欠けるものであ
った。Comparative Example 2 A yarn was produced and a fabric was woven in the same manner as in Example 1 except that no antioxidant was added. After scouring this woven fabric by the usual method,
Heat treatment was performed at 180 ° C. for 1 minute. The yellowing degree, dyeability and dimensional stability of the obtained fabric were as shown in Table 1. The dyeability was good, but the dimensional stability was poor in quality.
【００２５】比較例３ 酸化防止剤の付与を紡糸油剤付与後に行った以外は実施
例１と同様に糸を製造し、布帛を製織し、精練、熱処理
を行った。得られた布帛の黄変度、染色性、寸法安定性
は表１のようになり、寸法安定性は良好であったが、染
色性はやや品位に欠けるものであった。Comparative Example 3 A yarn was produced in the same manner as in Example 1 except that the application of the antioxidant was carried out after the application of the spinning oil, the fabric was woven, scoured and heat-treated. The yellowing degree, dyeability and dimensional stability of the obtained fabric were as shown in Table 1, and the dimensional stability was good, but the dyeability was somewhat lacking in quality.
【００２６】[0026]
【表１】 [Table 1]
【００２７】[0027]
【発明の効果】本発明により、耐熱性に優れ、また均染
性に優れたポリアミド系繊維を効率的に製造することが
できる。According to the present invention, polyamide fibers having excellent heat resistance and excellent levelness can be efficiently produced.
───────────────────────────────────────────────────── フロントページの続き Ｆターム(参考） 4L033 AA08 AB01 AC01 AC05 AC15 BA07 BA57 BA58 BA78 BA79 4L035 BB31 BB59 EE01 EE20 FF10 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4L033 AA08 AB01 AC01 AC05 AC15 BA07 BA57 BA58 BA78 BA79 4L035 BB31 BB59 EE01 EE20 FF10
Claims (2)
ーが固化した以降で、未延伸糸に紡糸油剤を付与して捲
き取る以前に、酸化防止剤を付与することを特徴とする
耐熱性ポリアミド系繊維の製造方法。An antioxidant is added to the unstretched yarn after applying the spinning oil to the undrawn yarn after the polyamide has been melt-spun and the polymer has been solidified. Fiber manufacturing method.
上である請求項１記載の耐熱性ポリアミド系繊維の製造
方法。 １）ヒンダードアミン系化合物 ２）ヒンダードフェノール系化合物 ３）セミカルバジド系化合物2. The method according to claim 1, wherein the antioxidant is at least one of the following compounds. 1) Hindered amine compounds 2) Hindered phenol compounds 3) Semicarbazide compounds
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11140594A JP2000328357A (en) | 1999-05-20 | 1999-05-20 | Production of heat-resistant polyamide-based fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11140594A JP2000328357A (en) | 1999-05-20 | 1999-05-20 | Production of heat-resistant polyamide-based fiber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000328357A true JP2000328357A (en) | 2000-11-28 |
Family
ID=15272335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11140594A Pending JP2000328357A (en) | 1999-05-20 | 1999-05-20 | Production of heat-resistant polyamide-based fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2000328357A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003038183A1 (en) * | 2001-10-31 | 2003-05-08 | Kanebo, Limited | Method of dyeing woven fabric comprising polyamide fiber |
-
1999
- 1999-05-20 JP JP11140594A patent/JP2000328357A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003038183A1 (en) * | 2001-10-31 | 2003-05-08 | Kanebo, Limited | Method of dyeing woven fabric comprising polyamide fiber |
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