JPH0375664B2 - - Google Patents
Info
- Publication number
- JPH0375664B2 JPH0375664B2 JP57217737A JP21773782A JPH0375664B2 JP H0375664 B2 JPH0375664 B2 JP H0375664B2 JP 57217737 A JP57217737 A JP 57217737A JP 21773782 A JP21773782 A JP 21773782A JP H0375664 B2 JPH0375664 B2 JP H0375664B2
- Authority
- JP
- Japan
- Prior art keywords
- fibers
- antibacterial
- compound
- polyamide
- compounds
- 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 - Lifetime
Links
- 239000000835 fiber Substances 0.000 claims description 42
- 230000000844 anti-bacterial effect Effects 0.000 claims description 40
- -1 polypropylene Polymers 0.000 claims description 29
- 229920002647 polyamide Polymers 0.000 claims description 25
- 239000004952 Polyamide Substances 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- 239000004753 textile Substances 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 6
- 229920003986 novolac Polymers 0.000 claims description 6
- 229940044654 phenolsulfonic acid Drugs 0.000 claims description 6
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 5
- 239000001263 FEMA 3042 Substances 0.000 claims description 5
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 5
- 229920002258 tannic acid Polymers 0.000 claims description 5
- 229940033123 tannic acid Drugs 0.000 claims description 5
- 235000015523 tannic acid Nutrition 0.000 claims description 5
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical group OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 claims description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 claims description 3
- NCDBYAPSWOPDRN-UHFFFAOYSA-N 2-[dichloro(fluoro)methyl]sulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)F)C(=O)C2=C1 NCDBYAPSWOPDRN-UHFFFAOYSA-N 0.000 claims description 3
- HFOCAQPWSXBFFN-UHFFFAOYSA-N 2-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=CC=C1C=O HFOCAQPWSXBFFN-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229920002972 Acrylic fiber Polymers 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims description 3
- 229920000297 Rayon Polymers 0.000 claims description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 3
- 239000013522 chelant Substances 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- CSOLXXUDCWOBSG-UHFFFAOYSA-N methyl n-(6-octylsulfonyl-1h-benzimidazol-2-yl)carbamate Chemical compound CCCCCCCCS(=O)(=O)C1=CC=C2N=C(NC(=O)OC)NC2=C1 CSOLXXUDCWOBSG-UHFFFAOYSA-N 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 239000002964 rayon Substances 0.000 claims description 3
- 229920003987 resole Polymers 0.000 claims description 3
- 229920001864 tannin Polymers 0.000 claims description 3
- 235000018553 tannin Nutrition 0.000 claims description 3
- 239000001648 tannin Substances 0.000 claims description 3
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims description 3
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 235000009120 camo Nutrition 0.000 claims description 2
- 235000005607 chanvre indien Nutrition 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011487 hemp Substances 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 19
- 230000000843 anti-fungal effect Effects 0.000 description 13
- 238000004043 dyeing Methods 0.000 description 9
- 230000001877 deodorizing effect Effects 0.000 description 6
- 238000007598 dipping method Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229940121375 antifungal agent Drugs 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 4
- 235000019645 odor Nutrition 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- YWJUZWOHLHBWQY-UHFFFAOYSA-N decanedioic acid;hexane-1,6-diamine Chemical compound NCCCCCCN.OC(=O)CCCCCCCCC(O)=O YWJUZWOHLHBWQY-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
本発明は、抗菌性を有するポリアミド系繊維製
品、特に耐久性のある防菌防黴力を有せる衛生的
なポリアミド系繊維製品の製造法に関する。
ポリアミド系繊維製品はスポーツウエア、ソツ
クス、パンテイストツキング等の各種衣料、寝装
製品、インテリア製品などに使用されている。
我々の生活空間にはさまざまな黴、細菌、バク
テリアが存在しており、高温多湿の環境下ではそ
れらの繁殖が特に活発になり、繊維の変質・変
色、劣化等の現象を起こしたり、水虫に侵された
り、腐敗、発酵現象を起こしたり、不快な臭気を
発生したりしていた。従つて、より清潔で、悪臭
を漂よわす事なく、快適で安全なポリアミド系繊
維製品の開発が望まれていた。
従来から防菌防黴加工法としては、繊維に有機
錫、有機水銀化合物を適用する方法が使用されて
いたが、最近これらの化合物の毒性が問題視さ
れ、ほとんど大部分が使用中止になつている。最
近では特に安全性の高い防菌防黴剤として第４級
アンモニウム塩が注目されており、特にセルロー
ス系繊維に対し反応性を持つたシリコーン系第４
級アンモニウム塩が洗濯耐久性のある加工剤とし
て注目されている。
しかしながら、シリコーン系第４級アンモニウ
ム塩の場合にはセルロース系繊維に対してのみ反
応性を持ち耐久性のある防菌防黴効果を示すが、
ポリアミド系繊維については一時的な防菌防黴効
果しか得られていない。また、他の安全性の高い
防菌防黴加工剤についてもポリウレタン系繊維含
有製品に対してはある程度の耐久性のある防菌効
果のあることがいわれているがポリアミド系繊維
に対し耐久性のある防菌防黴効果のある加工法は
未だ開発されていない。
従つて、本発明の目的は、耐久性のある防菌防
黴力を有するポリアミド系繊維製品の製造法を提
供するにある。
本発明に係る抗菌性を有するポリアミド系繊維
製品の製造法は、ポリアミド系繊維100％から成
る繊維製品又はポリアミド系繊維にアクリル系繊
維、ポリエステル系繊維、ポリビニール系繊維、
ポリプロピレン系繊維、ポリエチレン系繊維、キ
ユプラ、レーヨン、アセテート等の再生セルロー
ス系繊維あるいは綿、ウール、絹、麻等の天然繊
維から選ばれた少なくとも一種の繊維が混用され
た繊維製品に抗菌加工剤を付与すると同時もしく
は付与した後にアニオン系フエノール化合物を付
与するポリアミド系繊維製品の製造法であつて、
前記抗菌加工剤が５−クロロ−２−（２，４−
ジクロロフエノキシ）フエノール、Ｎ−（フルオ
ロジクロロメチルチオ）−フタルイミド、Ｎ−ジ
メチル−N′−フエニル−（N′−フルオロジクロロ
メチルチオ）−スルフアミド、１，６−ジ−（４−
クロロフエニルジクアジニド）ヘキサン、２−
（４−チアゾリル）ベンズイミダゾール、２−メ
トキシカルボニルアミノ−ベンズイミダゾール、
２−（チオシアナートメチルチオ）ベンゾチアゾ
ール、ジヨードメチル−Ｐ−トリルスルホン、Ｎ
−トリクロルメチルチオ−４−シクロヘキセン−
１，２ジカルボキシイミド、２−メトキシカルボ
ニルアミノ−５−オクチルスルフオニルベンズイ
ミダゾールの中から選ばれた少なくとも一種の化
合物であり、前記アニオン系フエノール化合物
が、タンニン、タンニン酸、タンニン酸・吐酒
石、フエノールスルホン酸ホルムアルデヒド樹
脂、ノボラツク型樹脂のスルホン化合物、ノボラ
ツク型樹脂のメタンスルホン酸、レゾール型樹脂
のメタンスルホン酸、ベンジル化フエノールスル
ホン酸、チオフエノール系化合物、ジ・ヒドロオ
キシ、ジ・フエニルスルホン系化合物、リガント
化合物及びこれらの金属キレート化合物の中から
選ばれた少なくとも一種の化合物であることを特
徴とする。
なおここでいう繊維製品とは糸、織物、編物
（ソツクス等の成形品を含む）等を含むものとす
る。
本発明で用いるポリアミド系繊維としては、主
鎖中にアミド結合をもつ重合体であればよく特に
限定されないが、例えばナイロン６、ナイロン６
６、ナイロン６・１０、ナイロン４、ナイロン８
等のポリアミド繊維ならびにウール、絹等が挙げ
られる。これらのポリアミド系繊維は、それら単
独からなる糸、織物、編物などの形態の繊維製品
として用いることができるし、あるいは、アクリ
ル、ポリエステル等の合成繊維、キユラプ、レー
ヨン、アセテート等の再生セルロース繊維あるい
は綿等の天然繊維等との交撚、交編、交織、混紡
等により混用された形態の繊維製品として用いる
こともできる。
本発明に使用される抗菌加工剤としては自然界
に生息する微生物である細菌類やカビ類に対し抗
微生物効果があり細菌類やカビ類の繁殖を防ぎ、
腐敗、発酵現象による悪臭を阻止し、更に衣類の
脆化変色、伝染性疾患を抑制し、人体に対し安全
性の高い加工剤が使用される。そのような抗菌剤
の用具例としては、５−クロロ−２−（２，４−
ジクロロフエノキシ）フエノール、Ｎ−（フルオ
ロジクロロメチルチオ）−フタルイミド、Ｎ−ジ
メチル−N′−フエニル−（N′−フルオロジクロロ
メチルチオ）−スルフアミド、１，６−ジ−（４−
クロロフエニルジクアジニド）ヘキサン、２−
（４−チアゾリル）ベンズイミダゾール、２−メ
トキシカルボニルアミノ−ベンズイミダゾール、
２−（チオシアナートメチルチオ）ベンゾチアゾ
ール、ジヨードメチル−Ｐ−トリルスルホン、Ｎ
−トリクロルメチルチオ−４−シクロヘキセン−
１，２ジカルボキシイミド、２−メトキシカルボ
ニルアミノ−５−オクチルスルフオニルベンズイ
ミダゾール等が挙げられる。
本発明で使用されるアニオン系フエノール化合
物としては、タンニン、タンニン酸、タンニン
酸・吐酒石、フエノールスルホン酸ホルムアルデ
ヒド樹脂、ノボラツク型樹脂のスルホン化物、ノ
ボラツク型樹脂のメタンスルホン酸、レゾール型
樹脂のメタンスルホン酸、ベンジル化フエノール
スルホン酸、チオフエノール系化合物、ジ・ヒド
ロオキシ、ジ・フエニルスルホン系化合物、リガ
ント化合物及びこれらの金属キレート化合物等が
挙げられる。
本発明において、抗菌加工剤は有機溶剤溶液、
エマルジヨン液または水分散液の形態で適用でき
るが、特に、有機溶剤を含まず、界面活性剤で水
中に分散させた形態で使用するのが有利である。
抗菌加工剤のポリアミド系繊維製品に対する使
用量は、抗菌加工剤の抗菌力およびポリアミド系
繊維製品が使用される用途およびポリアミド系繊
維の混用比率により適宜調整すれば良いが、一般
的にはポリアミド系繊維に対し0.01〜10％owfの
範囲である。
本発明において抗菌加工剤と併用するアニオン
性フエノール化合物の使用量はポリアミド系繊維
に対し１〜20％owf、好ましくは３〜10％owfの
範囲である。アニオン系フエノール化合物が１％
owf以下の場合には耐久性のある防菌防黴効果が
達成されず、また、20％owf以上では防菌防黴性
の耐久性は良好であるが風合が硬くなり好ましく
ない。
前記抗菌加工剤とアニオン系フエノール化合物
をポリアミド系繊維製品に同時に付与する方法と
しては、抗菌加工剤とアニオン系フエノール化合
物を液中で混合して同浴とし、この浴を用いて染
色前、染色時または染色後に繊維製品を浸漬処理
する方法あるいは混合液を繊維製品にパデイング
する方法または混合液を繊維製品にスプレーする
方法があげられる。また、抗菌加工剤を付与した
後にアニオン系フエノール化合物を付与する方法
としては、予め抗菌加工剤を染色時に付与して
後、浸漬法またはパデイング法もしくはスプレー
法にてアニオン系フエノール化合物を付与する方
法。または、染色した後に抗菌加工剤を浸漬法ま
たはパデイング法もしくはスプレー法で付与し、
その後でアニオン系フエノール化合物を浸漬法ま
たはパデイング法もしくはスプレー法で付与する
方法があげられる。抗菌加工剤とアニオン系フエ
ノール化合物を付与する方法は特にこれらの方法
に限定されることはないが、染色加工工程を含め
なるべく少い処理工程数を以つて抗菌加工剤をポ
リアミド系繊維製品に効率よく付与でき且つ性能
のバラツキを小さくできるという点からみれば、
染色時もしくは染色後に抗菌加工剤とアニオン系
フエノール化合物を同時に浸漬法により付与する
方法が好ましい。付与する温度としては20〜120
℃の範囲が通常使用できるが、40〜100℃の温度
であれば抗菌性のバラツキが小さく耐久性が良好
であるので好ましい。また、浸漬液のPHはPH７以
下であることが好ましい。PH値が７より大である
と染色物の色相が変化することがあるからであ
る。
本発明方法に従つて、浸漬、パデイング、また
はスプレーするのに用いる処理液中には樹脂加工
剤、柔軟剤、静電防止剤、撥水剤等を添加するこ
とができる。
以下、本発明を実施例について更に詳細に説明
する。
実施例 １
70d／24fのナイロン６６（旭化成工業(株)製）の
100％ジヤージーをスミノールミーリングレツド
RS3％owf、PH３で100℃で60分染色した。
この試料を４等分し、その第１の区分は、抗菌
加工剤として５−クロロ−２−（２，４−ジクロ
ロフエノキシ）フエノールの水分散液２％owfを
使用し、アニオン系フエノール化合物としてハイ
フイツクスGM（大日本製薬(株)製）５％owfを使
用し、浴比７：30、温度90℃で30分間撹拌しなが
ら処理した。比較列として、第２の区分は、アニ
オン系フエノール化合物の代りにカチオン系芳香
族化合物であるタンナロンＡ５％owf（川道製薬
(株)製）を用い同様に処理した。第３の区分は上記
抗菌加工剤のみを用い同様に処理した。第４の区
分は未加工処理品である。これらの防黴性能結果
を第１表に示す。
評価方法
洗濯方法
家庭用洗濯機を用いニユービーズ（花王石鹸(株)
製）２ｇ／、温度40℃、浴比１：40で５分間洗
濯し、その後脱液、脱水後、オーバーフローさせ
ながら10分間水洗する。これを洗濯１回とする。
防黴性能
JIS−2911にしたがつて試験を行なつた。試験
法はツアペツクドツクス寒天培地を水50ｇ／で
溶解し、PH＝5.5にし、殺菌処理した後、90mmφ
の滅菌シヤーレに入れて固化させる。この倍地の
上に、それぞれ試験試料を中心に置き、生理食塩
水に懸濁させたアスペルギルス・ニゲル
（ATCC6275）を噴霧器にて吹き付け、恒温恒湿
槽に入れ、温度30℃湿度90％で３日間培養させ黴
の発生状態を観察する。
◎試料に黴の発育はなく、試料の周囲に阻止帯を
形成している。
○試料の上に黴の発育がみられない。
×試料の上に黴の発育がみられる（試料面積の1/
２以下）。
××試料の上面1/2〜全面に黴の発育がみられる。
The present invention relates to a method for producing polyamide fiber products having antibacterial properties, particularly hygienic polyamide fiber products having durable antibacterial and antifungal properties. Polyamide fiber products are used in various clothing such as sportswear, socks, and pantyhose, bedding products, and interior products. Various molds, germs, and bacteria exist in our living spaces, and their reproduction becomes particularly active in hot and humid environments, causing phenomena such as deterioration, discoloration, and deterioration of fibers, as well as athlete's foot. They were contaminated, rotted, fermented, and emitted unpleasant odors. Therefore, it has been desired to develop polyamide fiber products that are cleaner, do not emit bad odors, are comfortable and safe. The conventional antibacterial and antifungal processing method has been to apply organic tin and organic mercury compounds to fibers, but recently the toxicity of these compounds has become a problem, and the use of most of them has been discontinued. There is. Recently, quaternary ammonium salts have been attracting attention as particularly safe antibacterial and fungicidal agents.
Grade ammonium salts are attracting attention as a finishing agent that is durable against washing. However, in the case of silicone-based quaternary ammonium salts, they are reactive only to cellulose-based fibers and exhibit durable antibacterial and antifungal effects.
For polyamide fibers, only temporary antibacterial and antifungal effects have been obtained. In addition, other highly safe antibacterial and antifungal finishing agents are said to have a certain degree of durable antibacterial effect on products containing polyurethane fibers, but they are said to have a durable antibacterial effect on products containing polyamide fibers. A processing method that has a certain antibacterial and antifungal effect has not yet been developed. Therefore, an object of the present invention is to provide a method for producing polyamide fiber products having durable antibacterial and antifungal properties. The method for producing a polyamide fiber product having antibacterial properties according to the present invention includes a fiber product made of 100% polyamide fiber, or a polyamide fiber containing acrylic fiber, polyester fiber, polyvinyl fiber, etc.
Applying antibacterial finishing agents to textile products that are mixed with at least one type of fiber selected from polypropylene fibers, polyethylene fibers, regenerated cellulose fibers such as Kyupra, rayon, acetate, or natural fibers such as cotton, wool, silk, and hemp. A method for producing a polyamide textile product in which an anionic phenol compound is applied at the same time as or after the application, the antibacterial finishing agent being 5-chloro-2-(2,4-
dichlorophenoxy)phenol, N-(fluorodichloromethylthio)-phthalimide, N-dimethyl-N'-phenyl-(N'-fluorodichloromethylthio)-sulfamide, 1,6-di-(4-
Chlorophenyl diquazinide) hexane, 2-
(4-thiazolyl)benzimidazole, 2-methoxycarbonylamino-benzimidazole,
2-(thiocyanatomethylthio)benzothiazole, diiodomethyl-P-tolylsulfone, N
-Trichloromethylthio-4-cyclohexene-
At least one compound selected from 1,2 dicarboximide, 2-methoxycarbonylamino-5-octylsulfonylbenzimidazole, and the anionic phenol compound is tannin, tannic acid, tannic acid, Tartar, phenolsulfonic acid formaldehyde resin, sulfone compounds of novolac type resin, methanesulfonic acid of novolac type resin, methanesulfonic acid of resol type resin, benzylated phenolsulfonic acid, thiophenol compounds, di-hydroxy, di-fluor It is characterized by being at least one compound selected from enylsulfone compounds, ligand compounds, and metal chelate compounds thereof. Note that the textile products mentioned here include yarn, woven fabrics, knitted fabrics (including molded products such as socks), etc. The polyamide fiber used in the present invention is not particularly limited as long as it is a polymer having an amide bond in the main chain, but for example, nylon 6, nylon 6
6, Nylon 6/10, Nylon 4, Nylon 8
Examples include polyamide fibers such as wool, silk, etc. These polyamide fibers can be used alone as fiber products in the form of yarn, woven fabrics, knitted fabrics, etc., or synthetic fibers such as acrylic and polyester, regenerated cellulose fibers such as Kyurap, rayon, acetate, etc. It can also be used as a mixed fiber product by twisting, knitting, weaving, blending, etc. with natural fibers such as cotton. The antibacterial finishing agent used in the present invention has an antimicrobial effect on bacteria and molds, which are microorganisms that live in the natural world, and prevents the growth of bacteria and molds.
A processing agent that is highly safe for the human body is used, as it prevents bad odors caused by putrefaction and fermentation phenomena, and also suppresses brittleness and discoloration of clothing and infectious diseases. Examples of such antimicrobial agents include 5-chloro-2-(2,4-
dichlorophenoxy)phenol, N-(fluorodichloromethylthio)-phthalimide, N-dimethyl-N'-phenyl-(N'-fluorodichloromethylthio)-sulfamide, 1,6-di-(4-
Chlorophenyl diquazinide) hexane, 2-
(4-thiazolyl)benzimidazole, 2-methoxycarbonylamino-benzimidazole,
2-(thiocyanatomethylthio)benzothiazole, diiodomethyl-P-tolylsulfone, N
-Trichloromethylthio-4-cyclohexene-
Examples include 1,2 dicarboximide and 2-methoxycarbonylamino-5-octylsulfonylbenzimidazole. The anionic phenol compounds used in the present invention include tannin, tannic acid, tannic acid/tartarite, phenolsulfonic acid formaldehyde resin, sulfonated products of novolac type resin, methanesulfonic acid of novolac type resin, and resol type resin. Examples include methanesulfonic acid, benzylated phenolsulfonic acid, thiophenol compounds, dihydroxy, diphenylsulfone compounds, ligand compounds, and metal chelate compounds thereof. In the present invention, the antibacterial finishing agent is an organic solvent solution,
It can be applied in the form of an emulsion or an aqueous dispersion, but it is particularly advantageous to use it in the form of an organic solvent-free dispersion in water with a surfactant. The amount of antibacterial finishing agent used for polyamide fiber products may be adjusted appropriately depending on the antibacterial effect of the antibacterial finishing agent, the purpose for which the polyamide fiber product is used, and the mixing ratio of polyamide fibers. It ranges from 0.01 to 10% owf based on the fiber. In the present invention, the amount of the anionic phenol compound used in combination with the antibacterial finishing agent is in the range of 1 to 20% owf, preferably 3 to 10% owf, based on the polyamide fiber. 1% anionic phenolic compound
If the owf is less than 20% owf, a durable antibacterial and antifungal effect cannot be achieved, and if the owf is more than 20% owf, the durability of the antibacterial and antifungal property is good, but the texture becomes hard, which is undesirable. As a method for simultaneously applying the antibacterial finishing agent and the anionic phenol compound to polyamide textile products, the antibacterial finishing agent and the anionic phenol compound are mixed in a liquid to form the same bath, and this bath is used to perform the dyeing process before dyeing. Examples include a method of dipping the textile product during or after dyeing, a method of padding the textile product with a mixed solution, or a method of spraying the mixed solution onto the textile product. In addition, as a method for applying an anionic phenol compound after applying an antibacterial finishing agent, a method is to apply an antibacterial finishing agent in advance during dyeing, and then apply an anionic phenol compound by dipping, padding, or spraying. . Alternatively, after dyeing, an antibacterial finishing agent is applied by dipping, padding or spraying,
After that, an anionic phenol compound may be applied by dipping, padding, or spraying. The method of applying the antibacterial finishing agent and anionic phenol compound is not particularly limited to these methods, but it is possible to efficiently apply the antibacterial finishing agent to polyamide fiber products by using as few processing steps as possible, including the dyeing process. From the point of view that it can be applied well and that variations in performance can be reduced,
A method in which an antibacterial finishing agent and an anionic phenol compound are simultaneously applied during or after dyeing by a dipping method is preferred. The temperature to apply is 20 to 120
A temperature range of 40°C to 100°C can usually be used, but a temperature of 40 to 100°C is preferable because it provides less variation in antibacterial properties and good durability. Moreover, it is preferable that the pH of the immersion liquid is PH7 or less. This is because if the PH value is greater than 7, the hue of the dyed material may change. According to the method of the present invention, resin processing agents, softeners, antistatic agents, water repellents, etc. can be added to the treatment liquid used for dipping, padding, or spraying. Hereinafter, the present invention will be explained in more detail with reference to Examples. Example 1 70d/24f nylon 66 (manufactured by Asahi Kasei Industries, Ltd.)
100% Jersey Sminol Milling Red
Staining was carried out at 100°C for 60 minutes with RS3%owf and PH3. This sample was divided into four equal parts, and the first division was divided into 2% OWF, an aqueous dispersion of 5-chloro-2-(2,4-dichlorophenoxy)phenol, as an antibacterial finishing agent, and anionic phenol. Hi-Fix GM (manufactured by Dainippon Pharmaceutical Co., Ltd.) 5% owf was used as a compound, and the treatment was carried out at a bath ratio of 7:30 and a temperature of 90° C. for 30 minutes with stirring. As a comparison column, the second category is a cationic aromatic compound instead of an anionic phenolic compound, Tannaron A 5% owf (Kawamichi Pharmaceutical Co., Ltd.).
(manufactured by Co., Ltd.) and treated in the same manner. The third section was treated in the same manner using only the above antibacterial finishing agent. The fourth category is unprocessed products. These antifungal performance results are shown in Table 1. Evaluation method Washing method Newbeads (Kao Soap Co., Ltd.) using a household washing machine
Washed at 40°C for 5 minutes at a bath ratio of 1:40, then deliquified and dehydrated, then washed with water for 10 minutes with overflow. This is considered one wash. Anti-mildew performance Tests were conducted in accordance with JIS-2911. The test method is to dissolve agar medium in 50g of water, adjust the pH to 5.5, sterilize it, and then add 90mmφ
Place in a sterilized crock pot to solidify. Place each test sample in the center on top of this medium, spray Aspergillus niger (ATCC6275) suspended in physiological saline with a sprayer, place it in a constant temperature and humidity chamber, and keep it at a temperature of 30°C and a humidity of 90% for 30 minutes. Incubate for several days and observe the state of mold development. ◎There is no mold growth on the sample, and an inhibition zone is formed around the sample. ○No mold growth is observed on the sample. ×Mold growth is observed on the sample (1/1/2 of the sample area)
2 or less). ××Mold growth is observed on the top 1/2 to the entire surface of the sample.
【表】
第１表から明らかな様に本発明法によるポリア
ミド繊維編物は、耐久性良好な防黴性能が得られ
た。一方、本発明法以外の方法では、初期の防黴
性能はよいが、洗濯１回することにより未加工品
と同様に全く防美性能が消失してしまうものしか
得られない。
実施例 ２
ナイロン６６、ウール、アクリル繊維（混率
40：40：20）から成るソツクス30足（1800ｇ）を
染色と同時に抗菌加工処理した。すなわち、カヤ
ノールミーリングブルーGW（日本化薬(株)製）３
％owf、PH３、浴比１：20の染色浴を調製し、こ
れに抗菌剤として実施例２で使用した２−（４−
チアゾリル）ベンズイミダゾールの水分散液90c.c.
を加えた。この浴を用いて100℃の温度で60分間
染色槽中で撹拌しながら染色と同様に抗菌剤の付
与を行なつた。染色後、脱液し、試料を３等分
し、(A)第１の区分はデマフイツクスＳ（明成化学
(株)製）５％owf液1.8、(B)第２の区分はハイフ
イツクスSL（大日本製薬(株)製）５％owf液1.8、
また(C)第３の区分はアニオン系フエノール化合物
を加えない比較対照液1.8で、それぞれ80℃の
温度で30分間撹拌しながら処理した。これらの防
菌剤性能及び防臭性能結果を第２表に示す。
評価方法
実施例１と同じ洗濯方法および防黴性能の測定
方法を用いた。
防菌性能
ハートインフユージヨン寒天培地を40ｇ／の
水で溶解し、120℃で滅菌処理した後、90mmφの
滅菌シヤーレに入れ固化させる。この培地の上
に、黄色ブドウ状球菌（スタヒロコツカス・アウ
レウスAATCC−6538P）を植種し、その上に試
料を置き37℃の温度で24時間培養を行なつた。
判定は防黴性同様に行なつた。
防臭性能
試験試料夫々に均一に人体から発生した汗を吸
収させて昼夜室温にて放置後密封容器の中に入
れ、20人の判定者が汗の臭いをかいだ。汗の不快
な臭いがしないと答えた人数により防臭性能を判
定した。多少バラツキがあつたが、14名以上が防
臭効果ありと答えたものを−とし、14名未満で10
名以上の場合を±とし、10名未満の場合を＋で表
示した。
着用テスト
20人の着用者が片足に未加工品、片足に(A)加工
品、または片足に未加工品、片足に(B)加工品、ま
たは片足に未加工品、片足に(C)加工品を１日８時
間宛着用して試験を行つた。試験結果の評価は、
未加工品に対し著じるしく防臭効果が有りと答え
た人のパーセントで示した。[Table] As is clear from Table 1, the polyamide fiber knitted fabric produced by the method of the present invention had good durability and anti-mildew performance. On the other hand, with methods other than the method of the present invention, the initial anti-mildew performance is good, but after one washing, the anti-beautifying performance completely disappears, just like the unprocessed product. Example 2 Nylon 66, wool, acrylic fiber (mixing ratio
30 pairs (1800 g) of socks consisting of 40:40:20) were dyed and treated with antibacterial treatment. That is, Kayanol Milling Blue GW (manufactured by Nippon Kayaku Co., Ltd.) 3
%owf, pH 3, bath ratio 1:20, and added 2-(4-
Aqueous dispersion of benzimidazole (thiazolyl) 90c.c.
added. Using this bath, an antibacterial agent was applied in the same way as dyeing while stirring in a dyeing tank at a temperature of 100°C for 60 minutes. After staining, the sample was dehydrated and divided into three equal parts.
(manufactured by Dainippon Pharmaceutical Co., Ltd.) 5% owf liquid 1.8, (B) the second category is Hi-Fix SL (manufactured by Dainippon Pharmaceutical Co., Ltd.) 5% owf liquid 1.8,
The third section (C) was a comparative solution 1.8 to which no anionic phenol compound was added, and each sample was treated with stirring at a temperature of 80° C. for 30 minutes. The antibacterial performance and deodorizing performance results are shown in Table 2. Evaluation method The same washing method and method for measuring antifungal performance as in Example 1 were used. Antibacterial performance Heart infusion agar medium is dissolved in 40g/water, sterilized at 120°C, and then placed in a 90mmφ sterile shear dish to solidify. Staphylococcus aureus (Staphylococcus aureus AATCC-6538P) was inoculated onto this medium, and a sample was placed thereon and cultured at a temperature of 37°C for 24 hours. Judgment was made in the same manner as for antifungal properties. Deodorizing performance Each test sample uniformly absorbed sweat generated from the human body, was left at room temperature day and night, and then placed in a sealed container, and 20 judges smelled the sweat. The deodorizing performance was judged based on the number of people who answered that there was no unpleasant odor of sweat. There was some variation, but if 14 or more people answered that it had a deodorizing effect, it was rated -, and if less than 14 people answered it was 10.
If there were more than 10 people, it was marked as ±, and if there were fewer than 10 people, it was shown as +. Wear test: 20 wearers wear one leg unfinished and one leg (A) treated, or one leg unfinished and one leg (B) treated, or one leg unfinished and one leg (C) treated. The test was conducted by wearing the product for 8 hours a day. Evaluation of test results is
It is expressed as the percentage of people who answered that it had a significant deodorizing effect compared to the unprocessed product.
【表】
第２表から明らかな様に本発明法により加工さ
れたソツクスは、防黴・防菌性能の耐久力に優れ
かつ、防臭性能の耐久力も非常に優れていること
が認められ、快適で衛生的なソツクスであること
が判る。[Table] As is clear from Table 2, the socks processed by the method of the present invention are recognized to have excellent durability in terms of anti-fungal and anti-bacterial properties, as well as excellent durability in deodorizing properties, and are comfortable. You can tell that they are hygienic socks.
Claims (1)
はポリアミド系繊維にアクリル系繊維、ポリエス
テル系繊維、ポリビニール系繊維、ポリプロピレ
ン系繊維、ポリエチレン系繊維、キユプラ、レー
ヨン、アセテート等の再生セルロース系繊維ある
いは綿、ウール、絹、麻等の天然繊維から選ばれ
た少なくとも一種の繊維が混用された繊維製品に
抗菌加工剤を付与すると同時もしくは付与した後
にアニオン系フエノール化合物を付与するポリア
ミド系繊維製品の製造法であつて、 前記抗菌加工剤が５−クロロ−２−（２，４−
ジクロロフエノキシ）フエノール、Ｎ−（フルオ
ロジクロロメチルチオ）−フタルイミド、Ｎ−ジ
メチル−N′、−フエニル−（N′−フルオロジクロ
ロメチルチオ）−スルフアミド、１，６−ジ−（４
−クロロフエニルジクアジニド）ヘキサン、２−
（４−チアゾリル）ベンズイミダゾール、２−メ
トキシカルボニルアミノ−ベンズイミダゾール、
２−（チオシアナートメチルチオ）ベンゾチアゾ
ール、ジヨードメチル−Ｐ−トリルスルホン、Ｎ
−トリクロルメチルチオ−４−シクロヘキセン−
１，２ジカルボキシイミド、２−メトキシカルボ
ニルアミノ−５−オクチルスルフオニルベンズイ
ミダゾールの中から選ばれた少なくとも一種の化
合物であり、 前記アニオン系フエノール化合物が、タンニ
ン、タンニン酸・吐酒石、フエノールスルホン酸
ホルムアルデヒド樹脂、ノボラツク型樹脂のスル
ホン化合物、ノボラツク型樹脂のメタンスルホン
酸、レゾール型樹脂のメタンスルホン酸、ベンジ
ル化フエノールスルホン酸、チオフエノール系化
合物、ジ・ヒドロオキシ、ジ・フエニルスルホン
系化合物、リガント化合物及びこれらの金属キレ
ート化合物の中から選ばれた少なくとも一種の化
合物であることを特徴とする抗菌性を有するポリ
アミド系繊維製品の製造法。[Claims] 1. Textile products made of 100% polyamide fibers or recycled polyamide fibers with acrylic fibers, polyester fibers, polyvinyl fibers, polypropylene fibers, polyethylene fibers, Kyupra, rayon, acetate, etc. A polyamide-based product in which an anionic phenol compound is applied at the same time or after applying an antibacterial finishing agent to a textile product that is a mixture of cellulose fibers or at least one type of fiber selected from natural fibers such as cotton, wool, silk, and hemp. A method for producing textile products, wherein the antibacterial finishing agent is 5-chloro-2-(2,4-
dichlorophenoxy)phenol, N-(fluorodichloromethylthio)-phthalimide, N-dimethyl-N', -phenyl-(N'-fluorodichloromethylthio)-sulfamide, 1,6-di-(4
-chlorophenyl diquazinide)hexane, 2-
(4-thiazolyl)benzimidazole, 2-methoxycarbonylamino-benzimidazole,
2-(thiocyanatomethylthio)benzothiazole, diiodomethyl-P-tolylsulfone, N
-Trichloromethylthio-4-cyclohexene-
at least one compound selected from 1,2 dicarboximide, 2-methoxycarbonylamino-5-octylsulfonylbenzimidazole, and the anionic phenol compound is tannin, tannic acid/tartarite, Phenolsulfonic acid formaldehyde resin, sulfone compound of novolac type resin, methanesulfonic acid of novolac type resin, methanesulfonic acid of resol type resin, benzylated phenolsulfonic acid, thiophenol compound, di-hydroxy, di-phenylsulfone type 1. A method for producing a polyamide fiber product having antibacterial properties, characterized in that the antimicrobial agent is at least one compound selected from compounds, ligand compounds, and metal chelate compounds thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21773782A JPS59112070A (en) | 1982-12-14 | 1982-12-14 | Production of polyamide fiber having anti-bacterial property |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21773782A JPS59112070A (en) | 1982-12-14 | 1982-12-14 | Production of polyamide fiber having anti-bacterial property |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59112070A JPS59112070A (en) | 1984-06-28 |
| JPH0375664B2 true JPH0375664B2 (en) | 1991-12-02 |
Family
ID=16708957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21773782A Granted JPS59112070A (en) | 1982-12-14 | 1982-12-14 | Production of polyamide fiber having anti-bacterial property |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59112070A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59163474A (en) * | 1983-03-04 | 1984-09-14 | 旭化成株式会社 | Production of anti-bacterial polyamide fiber |
| JPH0311080U (en) * | 1989-06-14 | 1991-02-01 | ||
| US6939554B2 (en) * | 2002-02-05 | 2005-09-06 | Michigan Biotechnology Institute | Antimicrobial polymer |
| CN103015164B (en) * | 2012-12-12 | 2015-10-28 | 嵊州雅戈尔毛纺织有限公司 | A kind of preparation method of antibacterial and deodorizing fabric |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5524188A (en) * | 1978-08-08 | 1980-02-21 | Ciba Geigy Ag | Novel halogenated phenolester*antibacterial containing it and its application |
| JPS563056A (en) * | 1979-06-20 | 1981-01-13 | Okamoto Co Ltd | Sanitary good and its preparation |
-
1982
- 1982-12-14 JP JP21773782A patent/JPS59112070A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5524188A (en) * | 1978-08-08 | 1980-02-21 | Ciba Geigy Ag | Novel halogenated phenolester*antibacterial containing it and its application |
| JPS563056A (en) * | 1979-06-20 | 1981-01-13 | Okamoto Co Ltd | Sanitary good and its preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59112070A (en) | 1984-06-28 |
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