JPS633075B2 - - Google Patents
Info
- Publication number
- JPS633075B2 JPS633075B2 JP10427984A JP10427984A JPS633075B2 JP S633075 B2 JPS633075 B2 JP S633075B2 JP 10427984 A JP10427984 A JP 10427984A JP 10427984 A JP10427984 A JP 10427984A JP S633075 B2 JPS633075 B2 JP S633075B2
- Authority
- JP
- Japan
- Prior art keywords
- silk
- methylol
- acid
- resistance
- carboxylic acid
- 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
- 239000000835 fiber Substances 0.000 claims description 14
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 claims description 7
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 6
- -1 methylol groups Chemical group 0.000 claims description 6
- 238000006482 condensation reaction Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000003672 processing method Methods 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 230000037303 wrinkles Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002932 luster Substances 0.000 description 3
- AWOUERYHOVSIAI-UHFFFAOYSA-N 2-(hydroxyamino)propanoic acid Chemical compound ONC(C)C(O)=O AWOUERYHOVSIAI-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229960002449 glycine Drugs 0.000 description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- YQGDEPYYFWUPGO-VKHMYHEASA-N (3s)-4-azaniumyl-3-hydroxybutanoate Chemical compound [NH3+]C[C@@H](O)CC([O-])=O YQGDEPYYFWUPGO-VKHMYHEASA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229960002298 aminohydroxybutyric acid Drugs 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 230000001153 anti-wrinkle effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
〔産業上の利用分野〕
本発明は絹の改質加工法、特に絹繊維に防しわ
性、防縮性、嵩高性等を付与して品質を向上させ
るための改質加工法に関する。
〔従来の技術〕
絹のこの種の改質加工法として、スチレン、メ
チルメタクリレート、(メタ)アクリルアミド等
のビニルモノマーを用いて絹糸にグラウト重合す
ることにより、増量すると共に、絹糸に防しわ
性、ヒートセツト性等を付与することが知られて
いる。
〔発明が解決しようとする問題点〕
ビニルモノマーを用いたものは防しわ性、ヒー
トセツト性等が不充分ではあるが付与される反
面、絹本来の長所である吸湿性、染色性、防電
性、風合いなどが損われるといつた問題を有して
いた。
〔問題点を解決するための手段〕
本発明は上記実情に鑑み、絹本来の風合い、光
沢、染色性、親水性等の長所を損うことなく、絹
繊維に防しわ性、防縮性、イージーケア性、嵩高
性、耐摩耗性等を付与して品質を向上する絹の改
質加工法を提供するものであり、
その特徴とするところは、
一般式
(式中、Rは水素、メチル、カルボン酸又はア
ルコール基である)
で表わされるアミノアルカンカルボン酸をメチロ
ール基の縮合反応触媒として、N―メチロールア
クリルアミド又はN―メチロールメタクリルアミ
ドにより絹繊維に化学加工を施すことにある。そ
の場合、アミノアルカンカルボン酸としてアミノ
酢酸(R=H),アミノプロピオン酸(R=
CH3),アミノコハク酸(R=CH2COOH)アミ
ノグルタル酸(CH2CH2COOH),ヒドロキシア
ミノプロピオン酸(CH2OH),アミノヒドロキ
シ酪酸(CH3CHOH)等がある。
〔作用〕
N―メチロールアクリルアミド又はN―メチロ
ールメタクリルアミド(100〜300g/l)に上記
縮合反応触媒10〜50g/lを加えた水溶液に絹糸
布を浸漬すると共に、70〜100%に脱液し、次い
で80℃以下で予備乾燥した後ほぼ125℃以下、100
℃以上の温度で2〜7分キユアリングを行うもの
で、N―メチロールアクリルアミド又はN―メチ
ロールメタクリルアミドのメチロール基を絹繊維
分子に化学結合して防しわ性、防縮性、嵩高性等
を付与すると共に、アミノアルカンカルボン酸を
メチロール基の縮合反応触媒として用いることに
より絹本来の風合い、染色性、親水性等を害さな
い上、ほぼ125℃以下で反応するため光沢の悪化、
黄変などを生じる虞れもない。
また、上記加工法において、さらにMgCl2を少
量添加することにより、キユアリング時間をさら
に短縮しても同様の効果が得られる。
また、公知のラジカル重合触媒を加えてビニル
基の反応を生じさせることにより、湿潤時のしわ
回復性とイージケア性の向上が得られる。また、
N―メチロールモノマーに未メチロール同族体を
併用することにより、繊維内充填効果が強調され
嵩高性の増加が得られる。
〔実施例 1〕
精練済みの平羽二重(12匁付)40gを次の組成
の処理浴に1分間浸漬し、2本ロールマングルで
脱液率95%に絞液した。
N―メチロールメタクリルアミド 200g
アミノコハク酸 20g
水 1000g
次に70℃で3分間予備乾燥し、さらに120℃で
5分間熱風キユアを行つた。その後キユア試料を
2g/l石鹸液にて70℃15分間リーピングし、水
洗、乾燥した(重量増加率15.8%)。
かくして得られた絹織物は、乾湿両防しわ性が
すぐれており、防縮性も高く、イージーケア性も
向上した。また絹本来の長所である嵩高な手触り
を呈し、光沢、白度は変らなかつた。
主な性能の試験結果を表1に示す。
[Industrial Field of Application] The present invention relates to a method for modifying silk, particularly for improving the quality of silk fibers by imparting wrinkle resistance, shrink resistance, bulkiness, etc. to silk fibers. [Prior Art] This type of modification processing method for silk involves grouting polymerization of silk threads with vinyl monomers such as styrene, methyl methacrylate, (meth)acrylamide, etc., thereby increasing the weight of the silk threads and imparting wrinkle resistance and wrinkle resistance to the silk threads. It is known to impart heat-setting properties and the like. [Problems to be solved by the invention] Products using vinyl monomers have insufficient wrinkle resistance, heat setting properties, etc., but on the other hand, they do not have the inherent advantages of silk, such as hygroscopicity, dyeability, and electrical resistance. However, there were problems such as loss of texture. [Means for Solving the Problems] In view of the above-mentioned circumstances, the present invention provides wrinkle-proofing properties, shrink-proofing properties, and easy-to-use silk fibers without impairing the inherent advantages of silk, such as texture, luster, dyeability, and hydrophilicity. It provides a silk modification processing method that improves quality by imparting care properties, bulkiness, abrasion resistance, etc., and its characteristics are as follows: (In the formula, R is hydrogen, methyl, carboxylic acid, or alcohol group) Chemically processed into silk fiber with N-methylol acrylamide or N-methylol methacrylamide using an aminoalkane carboxylic acid represented by the following as a catalyst for the condensation reaction of methylol groups. The goal is to do the following. In that case, the aminoalkane carboxylic acids include aminoacetic acid (R=H), aminopropionic acid (R=
CH 3 ), aminosuccinic acid (R=CH 2 COOH), aminoglutaric acid (CH 2 CH 2 COOH), hydroxyaminopropionic acid (CH 2 OH), and aminohydroxybutyric acid (CH 3 CHOH). [Operation] A silk cloth is immersed in an aqueous solution of N-methylol acrylamide or N-methylol methacrylamide (100 to 300 g/l) and 10 to 50 g/l of the above condensation reaction catalyst, and the liquid is dehydrated to 70 to 100%. , then after pre-drying at below 80℃, approximately below 125℃, 100
Curing is performed for 2 to 7 minutes at a temperature of ℃ or above, and the methylol group of N-methylol acrylamide or N-methylol methacrylamide is chemically bonded to silk fiber molecules to impart wrinkle resistance, shrink resistance, bulkiness, etc. In addition, by using aminoalkanecarboxylic acid as a catalyst for the condensation reaction of methylol groups, it does not impair silk's original texture, dyeability, hydrophilicity, etc., and since the reaction occurs at approximately 125°C or lower, it does not cause deterioration of gloss or
There is no risk of yellowing or the like. Further, in the above processing method, the same effect can be obtained even if the curing time is further shortened by further adding a small amount of MgCl 2 . Furthermore, by adding a known radical polymerization catalyst to cause a reaction of vinyl groups, improvements in wrinkle recovery properties and easy care properties when wet can be obtained. Also,
By using a non-methylol homolog in combination with the N-methylol monomer, the effect of filling the fibers can be emphasized and bulkiness can be increased. [Example 1] 40 g of refined flat feather doublet (with 12 momme) was immersed for 1 minute in a treatment bath having the following composition, and squeezed with a two-roll mangle to a liquid removal rate of 95%. N-methylolmethacrylamide 200g aminosuccinic acid 20g water 1000g Next, preliminary drying was performed at 70°C for 3 minutes, and hot air curing was further performed at 120°C for 5 minutes. Thereafter, the Cure sample was reaped in a 2 g/l soap solution at 70°C for 15 minutes, washed with water, and dried (weight increase rate: 15.8%). The thus obtained silk fabric had excellent dry and wet wrinkle resistance, high shrink resistance, and improved easy care properties. It also exhibited a bulky texture, which is an inherent advantage of silk, and its luster and whiteness remained unchanged. Table 1 shows the main performance test results.
精練済絹羽二重(10匁付)に次の処理浴を飽充
し、次いで90%に絞液し、70℃で3分間予備乾燥
した後、110℃で5分間キユアリングした。
N―メチロールアクリルアミド 150g
メタクリルアミド 50g
アミノ酢酸 15g
塩化マグネシウム 5g
過硫酸カリ 2g
水 1000g
本加工絹試料は表2のデータにみるように乾湿
防しわ性、イージーケア性、耐摩耗性、形態安定
性、嵩高性等の向上効果が顕著に認められ、しか
も絹本来の長所である吸湿性、通気性、剛軟度等
はほとんど損われず、絹繊維の品質向上が可能に
なつた。
Refined silk habutae (with 10 momme) was filled with the following treatment bath, then squeezed to 90%, pre-dried at 70°C for 3 minutes, and then cured at 110°C for 5 minutes. N-methylol acrylamide 150g Methacrylamide 50g Aminoacetic acid 15g Magnesium chloride 5g Potassium persulfate 2g Water 1000g As shown in the data in Table 2, this processed silk sample has excellent wrinkle resistance, easy care, abrasion resistance, and shape stability. The effect of improving bulkiness, etc. was significantly recognized, and the inherent advantages of silk, such as hygroscopicity, air permeability, bending resistance, etc., were hardly impaired, making it possible to improve the quality of silk fibers.
【表】
〔実施例 3〕
16匁付富士絹に次の処理浴を飽充(80%絞液)
し、80℃で3分間予備乾燥した後110℃で5分間
キユアした。
N―メチロールメタクリルアミド 200g
メタクリルアミド 100g
ヒドロキシアミノプロピオン酸 20g
塩化マグネシウム 10g
過硫酸アンモニウム 4g
水 1000g
絹紡糸使いの富士絹は本来非常に収縮しやすい
等の形態安定性に乏しい欠点があるが、この加工
によつてこるような欠点が解消されるが、加工率
は長繊維織物の場合よりも高くすることが必要で
ある。表3に試験結果を示す。[Table] [Example 3] 16 momme Fuji silk is filled with the following treatment bath (80% squeezed liquid)
After pre-drying at 80°C for 3 minutes, it was cured at 110°C for 5 minutes. N-Methylolmethacrylamide 200g Methacrylamide 100g Hydroxyaminopropionic acid 20g Magnesium chloride 10g Ammonium persulfate 4g Water 1000g Fuji silk, which is made using silk spinning, has the disadvantage of poor morphological stability such as being extremely susceptible to shrinkage, but this processing However, the processing rate must be higher than in the case of long-fiber woven fabrics. Table 3 shows the test results.
本発明は上記のとおり、
一般式
(式中、Rは水素、メチル、カルボン酸又はア
ルコール基である)
で表わされるアミノアルカンカルボン酸をメチロ
ール基の縮合反応触媒として、N―メチロールア
クリルアミド又はN―メチロールメタクリルアミ
ドにより絹繊維に化学加工を施すことにあるた
め、増量による嵩高性を得ることではなく(増量
率は10〜20%程度)、絹繊維内部に飽充されたモ
ノマー化合物のメチロール基がその後の低温キユ
アリングによつて絹分子に化学結合することによ
り従来得られなかつた程顕著な防しわ、防縮、イ
ージーケア性等が絹繊維に付与せられ、しかも高
温キユアの場合に生じる不都合がなく低温キユア
触媒の効力によつて絹の光沢は損われず、着色黄
変の副作用も起らないという効果がある。またN
―メチロールモノマーに未メチロール同族体を併
用するときは、繊維内充填効果が強調され、嵩高
性を増すこともできる。またビニル基の一部を重
合反応することによつて湿潤時のしわ回復性とイ
ージーケア性を向上できる等その効果は大きい。
As described above, the present invention has the general formula (In the formula, R is hydrogen, methyl, carboxylic acid, or alcohol group) Chemically processed into silk fiber with N-methylol acrylamide or N-methylol methacrylamide using an aminoalkane carboxylic acid represented by the following as a catalyst for the condensation reaction of methylol groups. The aim is not to obtain bulkiness by increasing the weight (the increase rate is about 10 to 20%), but rather the methylol groups of the monomer compound filled inside the silk fibers form silk molecules through the subsequent low-temperature curing. By chemically bonding to silk fibers, silk fibers are given remarkable anti-wrinkle, anti-shrinkage, easy-care properties, etc. that were previously unobtainable, and are free from the disadvantages that occur when curing at high temperatures. The effect is that the luster of the product is not impaired and the side effect of coloring and yellowing does not occur. Also N
- When a methylol monomer is used in combination with a non-methylol analogue, the effect of filling in the fibers is emphasized and bulkiness can also be increased. In addition, by polymerizing a portion of the vinyl group, it has great effects, such as improved wrinkle recovery properties and easy care properties when wet.
Claims (1)
ルコール基である) で表わされるアミノアルカンカルボン酸をメチロ
ール基の縮合反応触媒として、N―メチロールア
クリルアミド又はN―メチロールメタクリルアミ
ドにより絹繊維に化学加工を施すことを特徴とす
る絹の改質加工法。[Claims] 1. General formula (In the formula, R is hydrogen, methyl, carboxylic acid, or alcohol group) Chemically processed into silk fiber with N-methylol acrylamide or N-methylol methacrylamide using an aminoalkane carboxylic acid represented by the following as a catalyst for the condensation reaction of methylol groups. A silk modification processing method characterized by applying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10427984A JPS60246867A (en) | 1984-05-22 | 1984-05-22 | Modification processing of silk |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10427984A JPS60246867A (en) | 1984-05-22 | 1984-05-22 | Modification processing of silk |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60246867A JPS60246867A (en) | 1985-12-06 |
| JPS633075B2 true JPS633075B2 (en) | 1988-01-21 |
Family
ID=14376482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10427984A Granted JPS60246867A (en) | 1984-05-22 | 1984-05-22 | Modification processing of silk |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60246867A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2665656B2 (en) * | 1994-12-13 | 1997-10-22 | 鹿児島県 | Method for improving quality of dyed silk fabric |
-
1984
- 1984-05-22 JP JP10427984A patent/JPS60246867A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60246867A (en) | 1985-12-06 |
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