JPS5986632A - Antibacterial treatment - Google Patents

Antibacterial treatment

Info

Publication number
JPS5986632A
JPS5986632A JP19702982A JP19702982A JPS5986632A JP S5986632 A JPS5986632 A JP S5986632A JP 19702982 A JP19702982 A JP 19702982A JP 19702982 A JP19702982 A JP 19702982A JP S5986632 A JPS5986632 A JP S5986632A
Authority
JP
Japan
Prior art keywords
treatment
durability
treatment solution
organosilicone
antibacterial
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.)
Granted
Application number
JP19702982A
Other languages
Japanese (ja)
Other versions
JPH0230340B2 (en
Inventor
Kazuo Yasuda
一男 安田
Yasushi Funabashi
船橋 恭
Akie Chiyoda
千代田 昭惠
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.)
Toyobo Co Ltd
Original Assignee
Toyobo 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 Toyobo Co Ltd filed Critical Toyobo Co Ltd
Priority to JP19702982A priority Critical patent/JPS5986632A/en
Publication of JPS5986632A publication Critical patent/JPS5986632A/en
Publication of JPH0230340B2 publication Critical patent/JPH0230340B2/ja
Granted legal-status Critical Current

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  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

PURPOSE:To obtain a processed product having an antibcaterial activity of excellent durability without any problem of toxicity and any risk of discoloration, by adding a salt to a treatment solution and treating a polymer molding with the treatment solution containing an organosilane having a quat. ammonium salt group. CONSTITUTION:In the treatment of a polymer molding (e.g., fiber, synthetic paper or film of cellulose, polyamide, or the like) with an organosilicone having a quat. ammonium salt group [e.g., a compound of the formula (n=16-20)], organic and/or inorganic salts (e.g., Na2SO4, MgCl2 or propanolamine hydrochloride) are added to the treatment solution. It is possible to obtain efficiently a processed product having an antibacterial activity excellent in durability without detriment to whiteness and hand.

Description

【発明の詳細な説明】 本発明は甚分子成形品の抗菌処理方法に関するものであ
り、更に詳しくは第4級アンモニウム塩基を有するオル
ガノシリコーン加工の改良に関す1− る。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for antibacterial treatment of molecular molded articles, and more particularly to improvements in the processing of organosilicone with quaternary ammonium bases.

大体中には各種のカビ、細菌等の微生物が生息し、fa
fe品や人体に対しても有害作用を与えている。たとえ
ば衣料品、寝装品けもちろんのことインチリヤ製品、エ
フステリヤ製品等に至る広飾囲のIi!、維製品にも人
間の汁や飲食品等が付着し、これらの中の成分が栄養源
となってカビや細菌が@譬される。これらの微生物や微
生物から排出される排出物によって変色したり、繊維自
身が脆化したり、また悪臭発生の原因を生じる等衛生的
な問題も大きい。特に靴下、肌着、カジュアルウエア沖
や寝装用のシーツ、カバー類、航空気、船舶、車輌等の
内装材などにおいては繊維に付着した細菌類の生長、w
殖ならびにその拡散が人体の健康にとっても有害である
ことはもちろんである。
Generally, microorganisms such as various molds and bacteria live inside, and fa
It also has harmful effects on FE products and the human body. For example, we have a wide range of decorations ranging from clothing and bedding to Inchiriya products, Efsteriya products, etc. Human juices, food and beverages, etc. adhere to textile products, and the ingredients in these serve as a source of nutrients for mold and bacteria. These microorganisms and the waste discharged from them cause discoloration, embrittlement of the fibers themselves, and the generation of bad odors, which poses serious hygienic problems. In particular, the growth of bacteria attached to the fibers of socks, underwear, casual wear, bed sheets, covers, interior materials for aviation, ships, vehicles, etc.
It goes without saying that its growth and spread are harmful to human health.

従来、このような間舶を解決するために有機銅化合物、
有機銅化合物、ハロゲン化フェノール系化合物で処理す
る方法、第4級アンモニウム地基含有カチオン界面活性
剤で処理する方法、第4級アンモニウム塩基を有するビ
ニル系ポリマーで処[1する方法等が知られている。
Conventionally, organic copper compounds,
Methods of treatment with organocopper compounds, halogenated phenolic compounds, treatment with cationic surfactants containing a quaternary ammonium group, treatment with vinyl polymers having a quaternary ammonium group, etc. are known. There is.

しかしながら、これら公知の方法によるときは人体に対
する毒性の問題、処理廃液の公害問題、耐久性の欠如、
処理による変色の間顧等を有することから満足すべき方
法は知られていないのが実情である。特にル性等の問題
が少いことから第4級アンモニウム塩基lを不するカチ
オン性ポリマーが汀目されている(たとえば特公昭56
−45485号公報)。しかしながら、これら加工剤も
耐久性、風合に難点があるばかりでなく、白皮も低下し
易い欠点を有している。
However, when using these known methods, there are problems of toxicity to the human body, pollution problems of treated waste liquid, lack of durability,
The reality is that no satisfactory method is known, since it involves problems such as discoloration due to processing. In particular, cationic polymers that do not contain quaternary ammonium bases are attracting attention because they have fewer problems such as lubricity (for example, Japanese Patent Publication No. 56
-45485). However, these finishing agents not only have shortcomings in durability and texture, but also have the disadvantage of easily deteriorating white skin.

本発明者等はかかる欠点のない、しかも耐久性のすぐれ
た抗菌性を有する加工品を効率よく得る方法につき鋭意
研究の結果、本発明の処理方法に到達した。すなわち、
本発明は高分子成形品を、第4級アンモニウム塩基を有
するオルガノシリコーンで処理するに際し、処理液中に
有機および/または無機の塩類を添加することを特徴と
する。
The inventors of the present invention have conducted intensive research into a method for efficiently obtaining processed products that are free from such drawbacks and have excellent durability and antibacterial properties, and as a result, they have arrived at the treatment method of the present invention. That is,
The present invention is characterized by adding organic and/or inorganic salts to the treatment solution when treating a polymer molded article with an organosilicone having a quaternary ammonium base.

本発明の方法によるときは第4級アンモニウム塩基の存
在によるすぐれた抗菌性が付与されると共に、抗菌性の
耐久性が改善されること、処坤効れること等の特徴を有
している。ことに処J31剤のイ各 付着または反応効率のIい疎水性高分子に対しても親和
力の増加により高い反応効率が得られることは大きな利
点であり、この神の処理剤の用途を大巾に拡大すること
にもなる。
When the method of the present invention is used, excellent antibacterial properties are imparted due to the presence of the quaternary ammonium base, and the antibacterial durability is improved and the treatment is effective. In particular, it is a great advantage of the treatment agent J31 that high reaction efficiency can be obtained due to increased affinity for hydrophobic polymers that have low adhesion or reaction efficiency, and this is a major advantage of the treatment agent. It will also be expanded to.

本発明において用いられる第4級アンモニウム塩基を有
するオルガノシリコーンとしては、第3級窒素含有基、
たとえばジアルキルff、換アミノアルキル基を有する
シルキサン単位をもつジオルガノポリシロキサンを4級
化した構造のオルガノシリコーン、一般式 %式%( R:アルコキシ基、ハロゲン原子、アシル基、1個はヒ
ドロキシル基であってもよい。
The organosilicone having a quaternary ammonium base used in the present invention includes a tertiary nitrogen-containing group,
For example, an organosilicone having a structure obtained by quaternizing a diorganopolysiloxane having a silxane unit having a dialkyl ff or a converted aminoalkyl group, the general formula % formula % (R: alkoxy group, halogen atom, acyl group, one hydroxyl group) It may be.

R′:置換基を有していてもよい炭素原子数が20以下
の2価の炭化水素基または酬索原子、窒素原子を含有す
る炭素原子数が20以下の2価の炭化水素基であっても
よい。
R': A divalent hydrocarbon group having 20 or less carbon atoms which may have a substituent, or a divalent hydrocarbon group having 20 or less carbon atoms containing a chain atom or a nitrogen atom. It's okay.

R#:低級アルキル基、′RI′=炭素原子数が1〜2
0のアルキル基、アルケニル基、環状脂肪族炭化水素基
、芳香族基、アルアルキル基またはアルカリル基である
R#: lower alkyl group, 'RI' = number of carbon atoms is 1 to 2
0 alkyl group, alkenyl group, cycloaliphatic hydrocarbon group, aromatic group, aralkyl group or alkaryl group.

ni1〜3の正の整数、Xiアニオン、たとえば塩素原
子1、臭素原子等である。)で示されるオルガノシリコ
ーンが例示される。更に後者の好ま(但し、n:16〜
20) が例示される。該化合物は繊維上に耐水性皮膜を形成し
たり、特に後者の化合物では高分子成形品中に存在する
活性水素と反応して第4級アンモニウムカチオンが導入
され、各種カビや細菌に対してすぐれた制菌、殺菌効果
を有している。
A positive integer of ni1 to 3, a Xi anion, such as chlorine atom 1, bromine atom, etc. ) is exemplified. Furthermore, the latter is preferred (however, n: 16~
20) is exemplified. These compounds form a water-resistant film on fibers, and the latter compound in particular reacts with active hydrogen present in polymer molded products to introduce quaternary ammonium cations, making them highly effective against various molds and bacteria. It has antibacterial and bactericidal effects.

−例を挙げればクロカビ、アオカビ、コウジカビ、ケト
ミウム、クモノスカビdようなカビ類、大腸菌、黄色ブ
ドウ球菌、コリネバクテリウム菌、ダラム陰性棹状菌、
バチルス九、桿菌属、球菌属等の多くの細菌に対して制
菌、殺菌効果を示す。
- For example, molds such as black mold, blue mold, Aspergillus mold, chaetomium, spider mold d, Escherichia coli, Staphylococcus aureus, Corynebacterium, Durum negative rods,
It exhibits bactericidal and bactericidal effects against many bacteria such as Bacillus 9, Bacillus, and Coccus.

本発明の対象となる高分子成形品としては、たとえばセ
ルロース、蛋白系のような天然高分子、セルロースアセ
テートのような半合成高分子、ポリエステル、ポリアミ
ド、ポリビニルアルコール、ポリウレタン、ボリクラー
ル、ポリオレフィンのような合成高分子等からなる繊維
、合成2紙、フィルム、発゛泡体、その他の成形品およ
びそれらの接合品が挙げられる。特に繊維に適用して効
果的である。繊維とはバラ毛、糸条、スライバー、編織
物、不織布、敷物、テープ、縫製品等を包含するもので
ある。高分子峨紋と無iiH,絣維等の複合または混合
品であってもよい。
Examples of polymer molded articles to which the present invention applies include natural polymers such as cellulose and protein, semi-synthetic polymers such as cellulose acetate, polyesters, polyamides, polyvinyl alcohols, polyurethanes, polyclars, and polyolefins. Examples include fibers made of synthetic polymers, synthetic papers, films, foams, other molded products, and bonded products thereof. It is particularly effective when applied to fibers. Fibers include loose wool, threads, slivers, knitted fabrics, nonwoven fabrics, rugs, tapes, sewn products, and the like. It may be a composite or mixed product of polymer embossing, non-IIH, Kasuri fiber, etc.

繊維は単一素材のみならず、各種繊維の複合素材、混用
素材等任意でよい。
The fibers may be made of not only a single material but also composite materials of various fibers, mixed materials, etc.

本発明で用いるオルガノシリコーン、ことに上記一般式
で示されるオルガノシリコーンは浸漬法、スプレー法、
パッド法等の任意の方法により高分子成形品に付与され
、被処理成形品中のヒドロキロース、銅安レーヨン等の
セルロース系繊維のような活性基の多いときけ反応性も
高く、反応度80%以上の反応も比較的容易に得られる
が、活性基や膨潤性の少ない他の繊維等では反応度は5
0%以下となる。
The organosilicon used in the present invention, especially the organosilicon represented by the above general formula, can be prepared by dipping, spraying,
It is applied to a polymer molded article by any method such as the pad method, and when the treated molded article has many active groups such as cellulose fibers such as hydroxylose and copper ammonium rayon, the chemical reactivity is high, and the reactivity is 80. Although it is relatively easy to obtain a reaction of 5% or more, the degree of reaction is 5% for other fibers with active groups and less swelling property.
It becomes 0% or less.

反応度が低いと処理剤の利用効率が低いばかりか耐久性
不足、薬品コスト上昇、廃水の問題等を生じることにも
なる。
If the degree of reactivity is low, not only will the efficiency of using the treatment agent be low, but it will also lead to insufficient durability, increased chemical costs, and problems with waste water.

本発明の方法によるときは、処理液中に塩類を1、(加
することにより処理剤が高分子成形品に効果的に吸着さ
れ、処理剤の吸着効率が改善されることから浴比、の大
きい稀薄溶液での浸漬処理でも利用効率がすぐれること
、反応性も改善され耐久性が改良されること等の利点を
生じる。
When using the method of the present invention, the treatment agent is effectively adsorbed to the polymer molded article by adding 1.0% of salt to the treatment solution, and the adsorption efficiency of the treatment agent is improved. Even immersion treatment with a large dilute solution brings about advantages such as excellent utilization efficiency, improved reactivity, and improved durability.

また耐久性の改良はパッド・ドライ法、パッド・スチー
ム法等においても達成される。
Improvements in durability can also be achieved by pad dry methods, pad steam methods, and the like.

本発明において用いられる有機および無機の複動゛]と
しては、水溶性であれば特に制限されるものではないが
、特に1〜3価のカチオンのハロゲン化物、硫酸玲、硝
酸塩、リン酸、炭酸塩、酢酸塩、酒石酸塩等が挙げられ
、具体的には塩化す) IJウム、硫酸ナトリウム、炭
酸ナトリウム、酢酸ナトリウム、塩化マグネシウム、塩
化バリウム、硝酸マグネシウム、硝酸亜鉛、硫酸アルミ
ニウム、塩化アンモニウム、第2リン酸アンモニウム、
酢酸アンモニウム、Wj石mアンモニウム、プロパツー
ルアミン塩酸塩等が例示される。
The organic and inorganic double-acting compounds used in the present invention are not particularly limited as long as they are water-soluble, but in particular mono- to trivalent cation halides, sulfuric acid, nitrates, phosphoric acid, carbonic acid, etc. salt, acetate, tartrate, etc. (specifically chloride), sodium sulfate, sodium carbonate, sodium acetate, magnesium chloride, barium chloride, magnesium nitrate, zinc nitrate, aluminum sulfate, ammonium chloride, ammonium diphosphate,
Examples include ammonium acetate, Wjite ammonium, propatoolamine hydrochloride, and the like.

本発明の処理方法を更に詳しく He明すると、オルガ
ノシリコーンと塩類および所望により他処坤剤、助剤等
を含む水性液中で浸漬処理するのが好ましいが、該処理
液を含浸又は付与した後、乾燥または蒸熱処理する方法
等であってもよい。浸漬処理における処理温度は通常常
温〜80℃で充分であり、好ましくは40〜70℃であ
る。
To describe the treatment method of the present invention in more detail, it is preferable to immerse the organosilicone in an aqueous solution containing salts and optionally other additives, auxiliary agents, etc., after impregnating or applying the treatment solution. , drying, steaming treatment, etc. may also be used. The treatment temperature in the dipping treatment is usually room temperature to 80°C, preferably 40 to 70°C.

処理後は通常脱液後、乾燥、仕上げセットするのが好ま
しい。
After treatment, it is usually preferable to remove liquid, dry, and finish setting.

オルガノシリコーンの付与量は成形品重量に対し、通常
0.1〜3%であり、好ましくは0.5〜lである。ま
た塩類の使用歓は処理方法にもよるが成形品重量に対し
3〜30%程度が好ましい。
The amount of organosilicone applied is usually 0.1 to 3%, preferably 0.5 to 1, based on the weight of the molded product. The amount of salt to be used depends on the processing method, but it is preferably about 3 to 30% based on the weight of the molded product.

以下、実施例により本発明を説明する。The present invention will be explained below with reference to Examples.

実施例 L 染色されたポリエステルニットを液流染色機を使用し、
浴比l:15の水中で回転させながら下記式で示される
オルガノシリコン第4級アンモニウム塩1.0%owf
を添加し、均一に混合してからS熱水芒硝5%owfを
添加後、15分間で65℃に昇温し、その温度で20分
間処理した。
Example L The dyed polyester knit was dyed using a jet dyeing machine,
Organosilicon quaternary ammonium salt 1.0% owf represented by the following formula while rotating in water with a bath ratio of 1:15
was added and mixed uniformly, and then S hot water 5% OWF was added, the temperature was raised to 65° C. over 15 minutes, and the mixture was treated at that temperature for 20 minutes.

次いで遠心脱水後、乾燥し160’0でヒートセットを
行って抗菌処理を行った。なお、比較例として芒硝を添
加しない試料も作成した。これらの反応度はブpムフェ
ノールブルー呈色反応で残浴比色により測定した。
Next, after centrifugal dehydration, it was dried and heat set at 160'0 to perform antibacterial treatment. In addition, as a comparative example, a sample to which mirabilite was not added was also prepared. The degree of reactivity was measured by residual bath colorimetry using bpmphenol blue color reaction.

抗菌性は、Tl5−Z・2911−19’76のカビ抵
抗性試験法でテストした。
Antibacterial properties were tested using the mold resistance test method Tl5-Z.2911-19'76.

その結果芒硝を添加して抗菌処理した本発明は反応度が
90%となり、未添加の比較例の31%に比較して3倍
もの反応度向上が認められた。
As a result, the reactivity of the present invention treated with antibacterial treatment by adding Glauber's salt was 90%, which was 3 times higher than the 31% of the comparative example without the addition of Glauber's salt.

又、抗菌テストにおいても両者には明らかな差があり、
本発明の効果が顕著に詔められた。
Also, there is a clear difference between the two in antibacterial tests.
The effects of the present invention were clearly praised.

また、耐久性においても本発明による処理布が著しくす
ぐれていた。
Furthermore, the treated fabric according to the present invention was also significantly superior in durability.

実施例 2 染色されたナイロンパンティストッキングをパドル染色
枦を使用し、浴比1:30の水中で実施例りと同一のオ
ルガノシリコン第4級アンモニウム塩0.8%owfを
添加し、40℃に昇温してから硫安6%owfを添加し
、り1続き60℃に昇温させ、その温度で30分間処理
した。次いで遠心脱水後、足型に入れて115℃×5′
のスチームセットを行った。
Example 2 Dyed nylon pantyhose were dyed using a paddle dyeing machine, and 0.8% OWF of the same organosilicon quaternary ammonium salt as in Example was added in water at a bath ratio of 1:30, and heated to 40°C. After raising the temperature, 6% OWF of ammonium sulfate was added, and the temperature was then raised to 60° C., and the mixture was treated at that temperature for 30 minutes. Then, after centrifugal dehydration, it was placed in a foot mold at 115℃ x 5'
I did a steam set.

なお比較用として硫安未添加試料も作成した。For comparison, a sample without ammonium sulfate was also prepared.

実F6例1と同じように反応度と抗菌性をテストした結
果、オルガノシリコン第4級アンモニウム塩の反応度は
硫安添加したものが未添加に比較して2.5倍の85%
となった。又抗菌性も両者間に明らかな差が認められた
As a result of testing the reactivity and antibacterial properties in the same manner as in Example 1 of Actual F6, the reactivity of the organosilicon quaternary ammonium salt was 85% with the addition of ammonium sulfate, 2.5 times that of the unadded one.
It became. There was also a clear difference in antibacterial properties between the two.

実施例 染色されたポリエステル/綿(50150) 混紡フラ
イスニットをウィンス染色機で浴比1=20ノ水中に実
施例りと同一のオルガノシリコン第4級アンモニウム塩
1.5%owf 、食塩20%owfを添加し20分で
65℃に昇温し、その温度で45分間処理し、5分間水
洗し遠心脱水後、乾燥して抗菌処理を行った。なお比較
用として食塩未添加試料も作成した。反応度は処理布に
反応させたオルガノシリコン第4級アンモニウム塩の付
着状態をブロムフェノールブルーの呈色で観察した。
Example Dyeed polyester/cotton (50150) blended milled knit was dyed in a wince dyeing machine with a bath ratio of 1=20 and the same organosilicon quaternary ammonium salt as in Example 1.5% OWF and common salt 20% OWF. was added, the temperature was raised to 65° C. in 20 minutes, treated at that temperature for 45 minutes, washed with water for 5 minutes, centrifugally dehydrated, dried, and subjected to antibacterial treatment. For comparison, a sample to which no salt was added was also prepared. The degree of reactivity was determined by observing the state of adhesion of the organosilicon quaternary ammonium salt reacted to the treated fabric by observing the coloration of bromophenol blue.

その結果、食塩未添加抗菌処理布けほとんど綿の方にの
み加工剤が付着しているのに対し、食塩添加卯1理布は
ポリエステルと綿の両方に加工剤が均一に付着している
ことが観察できた。
As a result, the processing agent was found to be attached only to the cotton in most of the antibacterial treated fabrics without the addition of salt, whereas the processing agent was uniformly attached to both the polyester and cotton in the salt-added fabric. could be observed.

特許出願人  東洋紡績株式会社  11− 266−Patent applicant: Toyobo Co., Ltd. 11- 266-

Claims (1)

【特許請求の範囲】 L5分子成形品を、第4級アンモニウム塩基を有するオ
ルガノシリコーンで処理するに際し、処理液中に有機お
よび/または無機の塩類を添加することを特徴とする抗
菌処理方法。 z  第49アンモニウム塩基を有するオルガノシリコ
ーンが式 %式%) で示される化合物である特許請求の範囲第1項記軍、・
の抗菌処理方法。
[Scope of Claims] An antibacterial treatment method characterized by adding organic and/or inorganic salts to the treatment solution when treating an L5 molecule molded article with an organosilicone having a quaternary ammonium base. z The organosilicone having the 49th ammonium base is a compound represented by the formula %).
antibacterial treatment method.
JP19702982A 1982-11-09 1982-11-09 Antibacterial treatment Granted JPS5986632A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP19702982A JPS5986632A (en) 1982-11-09 1982-11-09 Antibacterial treatment

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP19702982A JPS5986632A (en) 1982-11-09 1982-11-09 Antibacterial treatment

Publications (2)

Publication Number Publication Date
JPS5986632A true JPS5986632A (en) 1984-05-18
JPH0230340B2 JPH0230340B2 (en) 1990-07-05

Family

ID=16367556

Family Applications (1)

Application Number Title Priority Date Filing Date
JP19702982A Granted JPS5986632A (en) 1982-11-09 1982-11-09 Antibacterial treatment

Country Status (1)

Country Link
JP (1) JPS5986632A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62282077A (en) * 1986-05-29 1987-12-07 東レ株式会社 Antibacterial electret fiber sheet
WO1994013748A1 (en) * 1992-12-04 1994-06-23 Warner-Lambert Company Durable antimicrobial surface treatment of plastic materials
KR20020042919A (en) * 2000-12-01 2002-06-08 박재준 A Manufacturing Method of Water Coating-remedy for Infraed-rayes, Antibiosis and Perfume
DE10141599B4 (en) * 2000-08-31 2004-08-05 Arteva Technologies S.A.R.L. Permanent, antimicrobial coating for plastic fibers and corresponding coating process
CN100344823C (en) * 2005-05-18 2007-10-24 东华大学 Textile grafted by quaternary ammonium group and grafting method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4844181A (en) * 1971-10-04 1973-06-25
US3958059A (en) * 1973-10-01 1976-05-18 The Procter & Gamble Company Fabric treatment composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4844181A (en) * 1971-10-04 1973-06-25
US3958059A (en) * 1973-10-01 1976-05-18 The Procter & Gamble Company Fabric treatment composition

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62282077A (en) * 1986-05-29 1987-12-07 東レ株式会社 Antibacterial electret fiber sheet
WO1994013748A1 (en) * 1992-12-04 1994-06-23 Warner-Lambert Company Durable antimicrobial surface treatment of plastic materials
DE10141599B4 (en) * 2000-08-31 2004-08-05 Arteva Technologies S.A.R.L. Permanent, antimicrobial coating for plastic fibers and corresponding coating process
KR20020042919A (en) * 2000-12-01 2002-06-08 박재준 A Manufacturing Method of Water Coating-remedy for Infraed-rayes, Antibiosis and Perfume
CN100344823C (en) * 2005-05-18 2007-10-24 东华大学 Textile grafted by quaternary ammonium group and grafting method thereof

Also Published As

Publication number Publication date
JPH0230340B2 (en) 1990-07-05

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