JPS6220312B2 - - Google Patents

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Publication number
JPS6220312B2
JPS6220312B2 JP54057910A JP5791079A JPS6220312B2 JP S6220312 B2 JPS6220312 B2 JP S6220312B2 JP 54057910 A JP54057910 A JP 54057910A JP 5791079 A JP5791079 A JP 5791079A JP S6220312 B2 JPS6220312 B2 JP S6220312B2
Authority
JP
Japan
Prior art keywords
dyed
fastness
dyes
polymer
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
JP54057910A
Other languages
Japanese (ja)
Other versions
JPS55152879A (en
Inventor
Toshio Ueda
Yoshinori Sato
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nitto Boseki Co Ltd
Original Assignee
Nitto Boseki Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nitto Boseki Co Ltd filed Critical Nitto Boseki Co Ltd
Priority to JP5791079A priority Critical patent/JPS55152879A/en
Publication of JPS55152879A publication Critical patent/JPS55152879A/en
Publication of JPS6220312B2 publication Critical patent/JPS6220312B2/ja
Granted legal-status Critical Current

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Description

【発明の詳細な説明】[Detailed description of the invention]

本発明はセルロース系繊維またはこれと他の繊
維からなる繊維材料を反応性染料または建染染料
を用いて染色した染色物の染色堅牢度を向上させ
る方法に関する。 反応性染料はその色彩の鮮明さと湿潤堅牢度の
優秀なることにより使用量は近年いちじるしい伸
びをみせている。しかしながら、反応性染料によ
る染色物の染色堅牢度に関しては2つの問題があ
る。 一つは耐酸加水分解性である。反応性染料は染
色の際、繊維と共有結合を生成し強固に結合する
が、染色されてからの経時中に酸等の影響によ
り、この結合が加水分解を受けて切断され、その
結果、湿潤による染料の脱落、他の衣類の汚染と
なつて現れる。 この問題に対する対策として、染色後、染色物
を特定のポリアミンの希薄水溶液によつて処理す
ることが行われており、かなりの効果が発揮され
ている。 二番目は耐塩素堅牢度の問題である。これは染
色物の洗濯のとき用いる水道水中に含まれる塩素
の作用により、染料が酸化されて染色物が退色な
いしは変色する現象である。現在までに開発され
ている前記ポリアミンによつて処理すると、前記
経時変化防止の目的を達成することはできても、
かえつて染料が水道水中の塩素の作用を受けやす
くなり変退色をむしろ助長することになる場合が
多い。このためこれに対する対策が求められてい
る。 また建染染料による染色物の染色堅牢度に関し
ても、他の堅牢度に関しては比較的問題はない
が、反応性染料の場合におけると同様、耐塩素堅
牢度が低く水道水によつて容易に変退色を生じ
る。 このような現状にかんがみ、本発明者は、反応
性染料の場合には耐酸加水分解性、耐洗濯性、耐
水性、耐汗性等の諸堅牢度を維持しながら耐塩素
堅牢度を向上させること、建染染料の場合には耐
塩素堅牢度を向上させることを目的として種々研
究を行なつて来た。 その結果、一般式 NH2−(CH2CH2NH)−oH (式中、nは1〜5である) で表されるポリエチレンポリアミン()とエピ
ハロヒドリン()の縮合によつて生成する、
()と()の仕込モル比が0.5〜2のポリマー
が上記目的を達成できる性能を有することを見出
し、それにより本発明を完成させるに至つた。 すなわち、本発明は反応性染料又は建染染料を
用いて染色した染色物の染色堅牢度を向上させる
に際し、上記ポリマーを用いて染色物を処理する
ことを特徴とする、染色物の染色堅牢度向上法に
関する。 本発明のポリマーを用いて処理された染色物の
耐酸加水分解性は秀れており、かつポリマーの電
荷密度が高いため、従来の処理剤に比べて約1/2
量で効果を生じるという利点を有する。 さらに耐塩素堅牢度に関してはきわめて良好な
性能を有し、本発明の方法により処理することに
よつて塩素による変退色がほとんど認められない
程度に改善できる。これは従来のポリアミンが塩
素による変退色をむしろ助長することと著しい対
照をなすものである。 また、水に対する堅牢度、洗濯に対する堅牢
度、汗に対する堅牢度に関しても良好な性能を有
する。 ただ、本発明のポリマーによる処理の場合、処
理による変色が例外的にレバフイツクスネービー
ブルーE−RA等の2、3の染料で見られること
があるが、このような場合には、処理液のPHを4
以下に保持すればこれを防止することができる。 本発明に使用されるポリマーの製造方法は下記
参考例において具体的に示すが、前述のポリエチ
レンポリアミンとエピハロヒドリンの混合物を水
または有機溶媒中で30〜100℃の範囲で加熱すれ
ば得られる。 これ等ポリマーは、水に容易に溶け、しかもPH
1〜14のすべての領域で水溶液として安定であ
る。 本発明に係るポリマーを用いて染色物を処理す
る方法としては、特に限定がなく、従来公知の方
法を適宜使用できる。例えば、該ポリマーを濃度
0.1g/〜2g/の水溶液中に、処理すべき
染色物を所定時間浸漬した後、水洗して乾燥させ
ればよい。浴比は通常1:10〜20であり、処理温
度は通常室温〜80℃であり、また処理時間は通常
5〜20分である。 本発明をより一層明らかにするため、以下に本
発明で用いるポリマーの合成例を参考例として示
めし、次いで実施例を示めす。 参考例 1 撹拌装置、還流冷却器、滴下ロートおよび温度
計を備えた反応容器中にエチレンジアミン361g
と水392gを入れ、撹拌して均一に溶解させた
後、加熱して温度を50℃まで上昇させる。この混
合物に滴下ロートからエピクロルヒドリン555g
を2時間で滴下した。滴下終了30分後、温度を80
℃に上げ、撹拌下で3時間反応させる。反応液の
粘度は次第に上昇し、縮合が進むのがわかる。反
応終了後、反応液10gをとり、500mlのアセトン
中に注ぐと白色沈澱を生じた。沈澱をガラスフイ
ルターを用いて過し、60℃で24時間減圧下乾燥
して6.8gの白色固体ポリマーを得た。収率は97
%であつた。 参考例 2 参考例1と同様の方法で、エチレンジアミン60
g、エピクロルヒドリン139gを水200g中で反応
させた。反応終了後、反応液10gをとり参考例1
と同様の処理をして4.8gの白色固体ポリマーを
得た。収率は98%であつた。 参考例 3〜6 参考例1におけるエチレンジアミンの代りにジ
エチレントリアミン、トリエチレンテトラミン、
テトラエチレンペンタミン、ペンタエチレンヘキ
サミンを夫々用いて、参考例1と同様の方法で、
エピクロルヒドリンと水中で反応させて白色固体
ポリマーを得た。結果を第1表に示す。
The present invention relates to a method for improving the color fastness of a dyed product obtained by dyeing cellulose fibers or fiber materials made of cellulose fibers and other fibers using reactive dyes or vat dyes. Reactive dyes have shown remarkable growth in usage in recent years due to their excellent color clarity and wet fastness. However, there are two problems regarding the color fastness of dyeings made with reactive dyes. One is acid hydrolysis resistance. During dyeing, reactive dyes form covalent bonds with fibers and form strong bonds; however, over time after dyeing, these bonds undergo hydrolysis and break due to the influence of acids, etc., resulting in moisture loss. This causes the dye to fall off and contaminate other clothing. As a countermeasure to this problem, the dyed product is treated with a dilute aqueous solution of a specific polyamine after dyeing, and this method has been shown to be quite effective. The second problem is the fastness to chlorine. This is a phenomenon in which dyes are oxidized by the action of chlorine contained in the tap water used when washing dyed products, causing fading or discoloration of dyed products. Although treatment with the polyamines developed to date can achieve the purpose of preventing aging,
In many cases, the dye becomes more susceptible to the action of chlorine in tap water, which actually promotes discoloration and fading. Therefore, countermeasures against this problem are required. Regarding the color fastness of dyed products using vat dyes, there is relatively no problem with other fastness properties, but as with reactive dyes, chlorine fastness is low and easily altered by tap water. Causes discoloration. In view of this current situation, the present inventor has developed a method for improving the chlorine fastness of reactive dyes while maintaining various fastness properties such as acid hydrolysis resistance, washing resistance, water resistance, and sweat resistance. In particular, in the case of vat dyes, various studies have been conducted with the aim of improving their chlorine fastness. As a result, it is produced by the condensation of polyethylene polyamine () represented by the general formula NH2- ( CH2CH2NH ) -oH (wherein n is 1 to 5 ) and epihalohydrin ().
It has been found that a polymer having a molar ratio of () to () of 0.5 to 2 has the ability to achieve the above object, and has thereby completed the present invention. That is, the present invention relates to improving the color fastness of a dyed product dyed using a reactive dye or a vat dye, which is characterized by treating the dyed product using the above-mentioned polymer. Regarding improvement methods. The acid hydrolysis resistance of dyed products treated with the polymer of the present invention is excellent, and because the polymer has a high charge density, it is about 1/2 that of conventional processing agents.
It has the advantage of being effective in small amounts. Furthermore, it has extremely good performance in terms of chlorine fastness, and by treatment according to the method of the present invention, it can be improved to such an extent that discoloration and fading due to chlorine is hardly observed. This is in sharp contrast to conventional polyamines, which actually promote discoloration and fading due to chlorine. It also has good performance in terms of fastness to water, fastness to washing, and fastness to sweat. However, in the case of treatment with the polymer of the present invention, discoloration due to treatment may be observed exceptionally with a few dyes such as Leverfix Navy Blue E-RA, but in such cases, the treatment solution PH of 4
This can be prevented by maintaining the following. The method for producing the polymer used in the present invention will be specifically shown in the following reference examples, and it can be obtained by heating the above-mentioned mixture of polyethylene polyamine and epihalohydrin in water or an organic solvent at a temperature in the range of 30 to 100°C. These polymers are easily soluble in water and have a pH of
It is stable as an aqueous solution in all regions of 1 to 14. There are no particular limitations on the method for treating dyed articles using the polymer according to the present invention, and conventionally known methods can be used as appropriate. For example, if the polymer is
The dyed article to be treated may be immersed in an aqueous solution of 0.1 to 2 g for a predetermined period of time, then washed with water and dried. The bath ratio is usually 1:10 to 20, the treatment temperature is usually room temperature to 80°C, and the treatment time is usually 5 to 20 minutes. In order to further clarify the present invention, synthesis examples of polymers used in the present invention are shown below as reference examples, and then examples are shown. Reference Example 1 361 g of ethylenediamine was placed in a reaction vessel equipped with a stirrer, reflux condenser, dropping funnel, and thermometer.
Add 392g of water and stir to dissolve uniformly, then heat to raise the temperature to 50℃. Add 555 g of epichlorohydrin from the dropping funnel to this mixture.
was added dropwise over 2 hours. 30 minutes after finishing dropping, lower the temperature to 80
℃ and react for 3 hours under stirring. It can be seen that the viscosity of the reaction solution gradually increases, and condensation progresses. After the reaction was completed, 10 g of the reaction solution was taken and poured into 500 ml of acetone to produce a white precipitate. The precipitate was filtered through a glass filter and dried under reduced pressure at 60° C. for 24 hours to obtain 6.8 g of a white solid polymer. Yield is 97
It was %. Reference Example 2 In the same manner as Reference Example 1, ethylenediamine 60
g, 139 g of epichlorohydrin was reacted in 200 g of water. After the reaction is complete, take 10g of the reaction solution and use it as reference example 1.
The same treatment as above was carried out to obtain 4.8 g of a white solid polymer. The yield was 98%. Reference Examples 3 to 6 In place of ethylenediamine in Reference Example 1, diethylenetriamine, triethylenetetramine,
In the same manner as in Reference Example 1 using tetraethylenepentamine and pentaethylenehexamine, respectively,
A white solid polymer was obtained by reaction with epichlorohydrin in water. The results are shown in Table 1.

【表】 実施例 1 上記参考例1〜6で得られたそれぞれのポリマ
ーの0.5g/水溶液を調製し、次いで下記反応
性染料を用い4%の濃度(対繊維重量)で浸漬法
で染色した染色綿布を浴比1:20、温度50℃で20
分間浸漬処理し、水洗した後、風乾した。用いた
染料は、バイエルAG(以下バイエルと略す)製
のレバフイツクスゴールデンイエローEG、バイ
エル製のレバフイツクスブリリアントレツドE−
4Bおよびバイエル製のレバフイツクスブリリア
ントレツドE−2Bである。 次に、この処理染色綿布の耐酸加水分解性を次
の方法で調べ未処理染色綿布の場合と比較した。
試験片を乳酸の10g/の溶液に浸漬した後、絞
り機を用い絞り率80%に絞り、120℃で4分間乾
燥させる。試験片が乾燥したら、2枚の添付白布
の間にはさんで、粗く縫い合わせ複合試験片を調
製する。その後は、水堅牢度試験方法(JIS−L
−0846)に準じて試験する。 結果を第2表に示す。未処理染色綿布の場合に
はいずれの染料の場合にも添付白布にかなりの汚
染が見られたが、本発明に係るポリマーを用いて
処理した染色布では、添付白布への汚染は全く認
められなかつた。
[Table] Example 1 A 0.5 g/aqueous solution of each of the polymers obtained in Reference Examples 1 to 6 above was prepared, and then dyed by dipping at a concentration of 4% (based on fiber weight) using the following reactive dye. dyed cotton cloth at a bath ratio of 1:20 and a temperature of 50°C.
After soaking for a minute, washing with water, and air drying. The dyes used were Leverfix Golden Yellow EG manufactured by Bayer AG (hereinafter abbreviated as Bayer) and Leverfix Brilliant Red E- manufactured by Bayer.
4B and Bayer's Leverfix Brilliant Red E-2B. Next, the acid hydrolysis resistance of this treated dyed cotton fabric was examined using the following method and compared with that of an untreated dyed cotton fabric.
After immersing the test piece in a solution of 10 g/lactic acid, it is squeezed using a squeezing machine to a squeezing rate of 80%, and dried at 120°C for 4 minutes. Once the test piece is dry, it is sandwiched between two attached white cloths and roughly sewn together to prepare a composite test piece. After that, the water fastness test method (JIS-L
-0846). The results are shown in Table 2. In the case of untreated dyed cotton fabrics, considerable staining of the attached white cloth was observed for all dyes; however, with the dyed fabrics treated using the polymer according to the present invention, no staining of the attached white cloth was observed. Nakatsuta.

【表】 実施例 2 上記参考例1〜6で得られたそれぞれのポリマ
ーの0.5g/の水溶液を調製し、次いで、下記
反応性染料を用い4%濃度(対繊維重量)で、浸
漬法又はプリント法で染色した染色綿布をポリマ
ー水溶液に浴比1:20、温度50℃で20分間浸漬処
理し水洗した後風乾した。用いた染料はバイエル
製のレバフイツクスゴールデンイエローG、チバ
ガイギー社(以下シバと略す)製のシバクロンネ
イビーブルーTRBE(以上は浸漬法で染色)、チ
バ製のシバクロンブリリアントブルー3R−P、
チバ製のシバクロンブリリアントブルーBR−P
(以上はプリント法で染色)である。 次に、この処理染色綿布の耐塩素堅牢度を次の
方法で調べ未処理染色布の場合と比較した。有効
塩素として50p.p.m.を含むPH8.0±0.2の緩衝液に
試験片を浸漬し(浴比1:100)、25℃で4時間
JIS L 0821の洗濯試験機にかける。その後流水
中で10分間洗い脱水し乾燥した。その結果を第3
表に示す。未処理染色綿布の場合にはいずれも著
しい退色を示したのに対し、参考例で示したポリ
マーで処理した染色綿布には変退色がみられず良
好な耐塩素堅牢度を有することが解る。
[Table] Example 2 A 0.5 g/aqueous solution of each of the polymers obtained in Reference Examples 1 to 6 above was prepared, and then the following reactive dye was used at a concentration of 4% (based on the weight of the fiber) using a dipping method or A dyed cotton fabric dyed by the printing method was immersed in an aqueous polymer solution at a bath ratio of 1:20 at a temperature of 50°C for 20 minutes, washed with water, and then air-dried. The dyes used were Leva Fix Golden Yellow G manufactured by Bayer, Cibacron Navy Blue TRBE (dyed by dipping method) manufactured by Ciba Geigy (hereinafter referred to as Ciba), Cibacron Brilliant Blue 3R-P manufactured by Ciba,
Ciba Cibacron Brilliant Blue BR-P
(The above is dyed using the printing method). Next, the chlorine fastness of this treated dyed cotton fabric was examined using the following method and compared with that of an untreated dyed fabric. The test piece was immersed in a buffer solution with a pH of 8.0 ± 0.2 containing 50 p.pm as available chlorine (bath ratio 1:100) and heated at 25°C for 4 hours.
Run it on a JIS L 0821 washing test machine. Thereafter, it was washed under running water for 10 minutes, dehydrated, and dried. The result is the third
Shown in the table. In contrast to the untreated dyed cotton fabrics that all showed significant discoloration, the dyed cotton fabrics treated with the polymer shown in the reference examples showed no discoloration and fading, indicating that they had good chlorine fastness.

【表】【table】

【表】 実施例 3 上記参考例1〜6で得られたそれぞれのポリマ
ーの0.5g/の水溶液を調製し、次いで、下記
建染染料を用い、2%濃度(対繊維重量)で染色
した染色綿布を、この溶液に浴比1:20、温度50
℃で20分間浸漬処理し、水洗した後、風乾した。
用いた染料は三井東圧化学株式会社(以下三井と
略す)製のミケスレンブリリアントブルーR、三
井製のミケスレンブリリアントブルー4G、三井
製のミケスレンブルー3G、三井製のミケスレン
ブルーRSNである。 次に、この処理染色綿布の塩素堅牢度を実施例
2で用いたのと同様の方法で試験し、その結果を
未処理染色布の場合と比較した。その結果を第4
表に示す。未処理染色綿布の場合には、いずれの
染料においても著しい変色を伴つた退色を示した
が、参考例で示したポリマーで処理した染色綿布
では変退色が見られず、建染染料の場合にも良好
な耐塩素堅牢度を有することが解る。
[Table] Example 3 A 0.5 g/aqueous solution of each of the polymers obtained in Reference Examples 1 to 6 above was prepared, and then dyed at a concentration of 2% (based on fiber weight) using the following vat dyes. Add cotton cloth to this solution at a bath ratio of 1:20 and a temperature of 50.
After soaking at ℃ for 20 minutes, washing with water, and air drying.
The dyes used were Mikethrene Brilliant Blue R manufactured by Mitsui Toatsu Chemical Co., Ltd. (hereinafter referred to as Mitsui), Mikethrene Brilliant Blue 4G manufactured by Mitsui, Mikethrene Blue 3G manufactured by Mitsui, and Mikethrene Blue RSN manufactured by Mitsui. . The treated dyed cotton fabric was then tested for chlorine fastness using a method similar to that used in Example 2, and the results were compared to the untreated dyed fabric. The result is the fourth
Shown in the table. In the case of untreated dyed cotton fabrics, all dyes exhibited discoloration accompanied by significant discoloration, but in the case of dyed cotton fabrics treated with the polymer shown in the reference example, no discoloration or fading was observed, and in the case of vat dyes. It can be seen that it also has good chlorine fastness.

【表】【table】

Claims (1)

【特許請求の範囲】 1 一般式 NH2−(CH2CH2NH)o−H (式中、nは1〜5である) で表されるポリエチレンポリアミン()1モル
に対し、エピハロヒドリン()0.5〜2モルの
縮合によつて生じるポリマーを用いて、セルロー
ス系繊維またはこれと他の繊維からなる繊維材料
を反応性染料または建染染料を用いて染色した染
色物を処理することを特徴とする染色物の染色堅
牢度向上法。
[Claims] 1. Epihalohydrin () per mole of polyethylene polyamine () represented by the general formula NH 2 -(CH 2 CH 2 NH) o -H (in the formula, n is 1 to 5). It is characterized by treating dyed products obtained by dyeing cellulose fibers or fiber materials consisting of cellulose fibers and other fibers with reactive dyes or vat dyes using 0.5 to 2 moles of a polymer produced by condensation. A method for improving the color fastness of dyed products.
JP5791079A 1979-05-11 1979-05-11 Enhancement of dye fastness Granted JPS55152879A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP5791079A JPS55152879A (en) 1979-05-11 1979-05-11 Enhancement of dye fastness

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP5791079A JPS55152879A (en) 1979-05-11 1979-05-11 Enhancement of dye fastness

Publications (2)

Publication Number Publication Date
JPS55152879A JPS55152879A (en) 1980-11-28
JPS6220312B2 true JPS6220312B2 (en) 1987-05-06

Family

ID=13069137

Family Applications (1)

Application Number Title Priority Date Filing Date
JP5791079A Granted JPS55152879A (en) 1979-05-11 1979-05-11 Enhancement of dye fastness

Country Status (1)

Country Link
JP (1) JPS55152879A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58115183A (en) * 1981-12-29 1983-07-08 大日本製薬株式会社 Chlorine fastness enhancing agent and method of dyed cotton fiber product
JPS57193583A (en) * 1981-05-14 1982-11-27 Sandoz Ag Improvement of dyeing fastness
CH673195B5 (en) * 1981-05-14 1990-08-31 Sandoz Ag
US4531946A (en) * 1983-03-09 1985-07-30 Diamond Shamrock Chemicals Company Aftertreatment of dyed cellulosic materials
DE3329029A1 (en) * 1983-08-11 1985-02-28 Cassella Ag, 6000 Frankfurt METHOD FOR PRODUCING COLORINGS WITH REACTIVE DYES
JPS60134080A (en) * 1983-12-16 1985-07-17 一方社油脂工業株式会社 Improvement in dyeability of fiber material, cationic fiber reactive product and its producton
JPS6134292A (en) * 1984-07-20 1986-02-18 株式会社日本触媒 Treatment of dyed article
DE3607963A1 (en) * 1986-03-11 1987-09-17 Bayer Ag CONDENSATION PRODUCTS AND METHOD FOR TREATING DYED POLYAMIDES
DE3709766A1 (en) * 1987-03-25 1988-10-06 Hoechst Ag METHOD FOR ALKALI-FREE DYEING WITH REACTIVE DYES

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