JPS6249392B2 - - Google Patents
Info
- Publication number
- JPS6249392B2 JPS6249392B2 JP14163281A JP14163281A JPS6249392B2 JP S6249392 B2 JPS6249392 B2 JP S6249392B2 JP 14163281 A JP14163281 A JP 14163281A JP 14163281 A JP14163281 A JP 14163281A JP S6249392 B2 JPS6249392 B2 JP S6249392B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- oil
- treated
- oil repellency
- formula
- 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
Links
- 239000004952 Polyamide Substances 0.000 claims description 11
- 229920002647 polyamide Polymers 0.000 claims description 11
- -1 phenol compound Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229920002994 synthetic fiber Polymers 0.000 claims description 7
- 239000012209 synthetic fiber Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005871 repellent Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000835 fiber Substances 0.000 description 7
- 235000013351 cheese Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical class CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- VJRSWIKVCUMTFK-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)F.FC(F)=C(F)C(F)(F)F.FC(F)=C(F)C(F)(F)F VJRSWIKVCUMTFK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229920006121 Polyxylylene adipamide Polymers 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229940116335 lauramide Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 229920006123 polyhexamethylene isophthalamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
本発明はポリアミド合成繊維に耐久性の優れた
撥水撥油加工を施す方法に関するものである。
ポリアミド合成繊維は強度、耐摩耗性、染色性
に優れた特長を持つているが、撥水性や撥油性に
乏しく、雨傘、レインコート、スノウウエア、作
業衣、カーペツトなど水や油の付着を嫌う用途に
は、撥水撥油加工をする必要があつた。しかし従
来用いられている加工剤は布帛表面に付着してい
るので、摩擦、揉み、洗濯などを繰り返すうちに
加工剤が脱落する欠点がある。
本発明者は繊維表面に撥水撥油性を持たせ、し
かも化学的に強固に結合して洗濯や摩擦などに耐
える加工法を検討し本発明に到つた。
即ち、本発明はポリアミド合成繊維を多価フエ
ノール化合物で処理した後、フエノール基との反
応性を有するパーフルオロ基含有化合物で処理し
て繊維表面に耐久性ある撥水撥油性を付与せしめ
る加工法である。
本発明で用いるポリアミドは、例えばポリ−ε
−カプラミド、ポリ−ω−ノナミド、ポリ−ω−
ラウリンアミドの如きω−アミノ酸又はω−ラク
タムからのポリアミド、ポリヘキサメチレンアジ
パミド、ポリヘキサメチレンセバカミド、ポリヘ
キサメチレンイソフタラミド、ポリキシリレンア
ジパミドの如きジアミンとジカルボン酸から得ら
れるポリアミド、これらの構成成分の共重合体、
これら各種重合体のポリマーブレンド体等を指
す。
これらポリアミドには必要に応じてつや消し
剤、熱安定剤、紫外線吸引剤、帯電防止剤、蛍光
増白剤、末端封鎖剤などが含まれていても良い。
本発明ではポリアミド合成繊維を先ず多価フエ
ノール化合物で処理する。本発明で用いる多価フ
エノール化合物は、フエノール基を2個以上持つ
た化合物であり、いわゆるフイツクス剤と呼ばれ
る化合物が好適である。例えば次に示すような化
合物が例示される。
The present invention relates to a method of applying a highly durable water- and oil-repellent finish to polyamide synthetic fibers. Polyamide synthetic fibers have excellent strength, abrasion resistance, and dyeability, but they are poor in water and oil repellency, and do not like the adhesion of water or oil to things such as umbrellas, raincoats, snowwear, work clothes, and carpets. For its intended use, it needed to be treated to be water and oil repellent. However, since the conventionally used finishing agents adhere to the surface of the fabric, there is a drawback that the finishing agents fall off during repeated rubbing, kneading, washing, etc. The present inventor has studied a processing method that imparts water and oil repellency to the surface of fibers, while chemically bonding them strongly to withstand washing, friction, etc., and has arrived at the present invention. That is, the present invention provides a processing method in which polyamide synthetic fibers are treated with a polyvalent phenol compound and then treated with a perfluoro group-containing compound that is reactive with phenol groups to impart durable water and oil repellency to the fiber surface. It is. The polyamide used in the present invention is, for example, poly-ε
-capramide, poly-ω-nonamide, poly-ω-
Polyamides from ω-amino acids or ω-lactams such as lauramide, diamines and dicarboxylic acids such as polyhexamethylene adipamide, polyhexamethylene sebacamide, polyhexamethylene isophthalamide, polyxylylene adipamide. polyamides, copolymers of these components,
It refers to polymer blends of these various polymers. These polyamides may contain a matting agent, a heat stabilizer, an ultraviolet absorbing agent, an antistatic agent, a fluorescent whitening agent, a terminal blocking agent, etc., as required. In the present invention, polyamide synthetic fibers are first treated with a polyphenol compound. The polyhydric phenol compound used in the present invention is a compound having two or more phenol groups, and compounds called so-called fixing agents are suitable. For example, the following compounds are exemplified.
【式】【formula】
【式】【formula】
【式】〔nは2〜4
の整数〕
これらの化合物はたとえばPH2〜6の水溶液と
して、0.1〜10%(owf)の濃度で繊維に付与され
る。
ポリアミド合成繊維を多価フエノールで処理し
た後、フエノール基との反応性を有するパーフル
オロ基含有化合物で処理する。フエノール基との
反応性を有する化合物としては例えば次に示すよ
うなものがあげられる。[Formula] [n is an integer of 2 to 4] These compounds are applied to the fibers at a concentration of 0.1 to 10% (owf), for example, as an aqueous solution with a pH of 2 to 6. After the polyamide synthetic fiber is treated with polyhydric phenol, it is treated with a perfluoro group-containing compound that is reactive with phenol groups. Examples of compounds having reactivity with phenol groups include the following.
【式】【formula】
【式】【formula】
次表に示す組成の液滴(直径5ミリメートル)
を試料上に3ケ置き、そのうち2ケ以上が10秒間
試料を濡らさずに液滴の状態を維持したか否かを
観察し、最上級のランクで撥水性を表す。
Droplets with the composition shown in the table below (5 mm in diameter)
Place three droplets on the sample and observe whether two or more of them maintain the state of droplets without wetting the sample for 10 seconds, and the highest rank indicates water repellency.
次表に示す組成の液滴(直径5ミリメートル)
を試料上に3ケ置き、そのうち2ケが3分間試料
を濡らさずに液滴の状態を維持したか否かを観察
し、最上級のランク点で撥油性を表わす。
Droplets with the composition shown in the table below (5 mm in diameter)
Three samples were placed on the sample, and two of them were observed to see if they remained in the form of droplets without wetting the sample for 3 minutes, and the highest rank indicates oil repellency.
カーペツトあるいは布帛の上を2万人が通行し
た後におけるカーペツトあるいは布帛の撥水性、
撥油性を評価したもの。
実施例 1
ポリεカプロラクタム繊維ブライト1000デニー
ル68フイラメントの捲縮加工染色糸2Kgをチーズ
染色機に入れ、多価フエノールスルホン酸誘導体
(商品名ナイロフイツクスTH、日本染化工業
(株))200gと水25lの溶液を注入して80℃で10分間
循環させた。続いて水を注入して水洗いを行なつ
た後一旦乾燥した。
次にN,N′−ジメチルホルムアミド25lに、ト
リエチルアミン500gとヘキサフルオロプロペン
3量体500gを混合した反応液を染色機に注入し
乾燥チーズに対し常温で1時間循環処理をした。
反応終了後、液を抜き、酢酸酸性水溶液で繊維を
洗い、続いて水洗いの後、チーズを乾燥した。
このように処理した糸条でループパイルカーペ
ツトを作り、撥水撥油性を評価したところ表1に
示すように優れた耐久性を示した。
比較例 1
実施例1と同一の繊維を用い、撥水撥油加工を
することなく、通常の方法でループパイルカーペ
ツトを作つた。このカーペツトに市販のフツ素系
防汚加工剤(アサヒガード730、明成化学工業
(株))を0.8owfスプレー塗布し、130℃で5分間熱
処理をした。
この製品の撥水撥油性は、通行テスト前では実
施例1の製品と同程度の性能を示したが通行テス
ト後は著しく性能が低下した。
評価結果を表1に示す
比較例 2
比較例1と同一の繊維で同一のカーペツトを作
り、防汚加工を全く施さずに評価した。
通行テスト前の製品で撥水撥油性は全く認めら
れなかつた。
評価結果を表1に示す。
Water repellency of carpet or fabric after 20,000 people pass over it;
Evaluation of oil repellency. Example 1 2 kg of crimped dyed yarn of polyε-caprolactam fiber bright 1000 denier 68 filament was put into a cheese dyeing machine, and a polyvalent phenolsulfonic acid derivative (trade name: Niro Fixx TH, manufactured by Nippon Someka Kogyo Co., Ltd.) was put into a cheese dyeing machine.
A solution of 200 g of Co., Ltd. and 25 liters of water was injected and circulated at 80°C for 10 minutes. Subsequently, water was injected to wash it, and then it was once dried. Next, a reaction mixture of 25 liters of N,N'-dimethylformamide, 500 g of triethylamine, and 500 g of hexafluoropropene trimer was poured into the dyeing machine, and the dried cheese was circulated at room temperature for 1 hour.
After the reaction was completed, the liquid was drained, the fibers were washed with an acetic acid aqueous solution, and then washed with water, and then the cheese was dried. A loop pile carpet was made from the yarn treated in this way and evaluated for water and oil repellency, and as shown in Table 1, it showed excellent durability. Comparative Example 1 Using the same fibers as in Example 1, a loop pile carpet was made in a conventional manner without water- and oil-repellent treatment. Commercially available fluorine-based antifouling agents (Asahi Guard 730, Meisei Chemical Industry Co., Ltd.)
Co., Ltd.) was sprayed at 0.8 owf and heat treated at 130°C for 5 minutes. The water and oil repellency of this product showed performance comparable to that of the product of Example 1 before the traffic test, but the performance deteriorated significantly after the traffic test. The evaluation results are shown in Table 1. Comparative Example 2 The same carpet as in Comparative Example 1 was made from the same fibers and evaluated without any antifouling treatment. No water or oil repellency was observed in the product before the road test. The evaluation results are shown in Table 1.
Claims (1)
で処理した後、フエノール基との反応性を有する
パーフルオロ基含有化合物で処理することを特徴
とするポリアミド合成繊維の撥水撥油加工方法。1. A method for water- and oil-repellent processing of polyamide synthetic fibers, which comprises treating polyamide synthetic fibers with a polyvalent phenol compound and then treating them with a perfluoro group-containing compound that is reactive with phenol groups.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14163281A JPS5846176A (en) | 1981-09-10 | 1981-09-10 | Water and oil repellent process of polyamide synthetic fiber |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14163281A JPS5846176A (en) | 1981-09-10 | 1981-09-10 | Water and oil repellent process of polyamide synthetic fiber |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5846176A JPS5846176A (en) | 1983-03-17 |
JPS6249392B2 true JPS6249392B2 (en) | 1987-10-19 |
Family
ID=15296548
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14163281A Granted JPS5846176A (en) | 1981-09-10 | 1981-09-10 | Water and oil repellent process of polyamide synthetic fiber |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5846176A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0211558A3 (en) * | 1985-07-26 | 1987-05-27 | Biodyne Chemicals, Inc. | Process for digesting lignocellulosic material |
JPH01306674A (en) * | 1988-06-03 | 1989-12-11 | Neos Co Ltd | Fluorine-containing phenolic fiber |
US5010387A (en) * | 1988-11-21 | 1991-04-23 | Honeywell Inc. | Solder bonding material |
-
1981
- 1981-09-10 JP JP14163281A patent/JPS5846176A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5846176A (en) | 1983-03-17 |
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