JPH0348603A - Antimicrobial and deodorizing material - Google Patents
Antimicrobial and deodorizing materialInfo
- Publication number
- JPH0348603A JPH0348603A JP1183005A JP18300589A JPH0348603A JP H0348603 A JPH0348603 A JP H0348603A JP 1183005 A JP1183005 A JP 1183005A JP 18300589 A JP18300589 A JP 18300589A JP H0348603 A JPH0348603 A JP H0348603A
- Authority
- JP
- Japan
- Prior art keywords
- antibacterial
- deodorizing
- agent
- halogen
- fiber
- 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.)
- Pending
Links
- 230000001877 deodorizing effect Effects 0.000 title claims abstract description 63
- 239000000463 material Substances 0.000 title claims abstract description 31
- 230000000845 anti-microbial effect Effects 0.000 title abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 150000001482 benzyl phenyl ethers Chemical class 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 70
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 32
- 239000000835 fiber Substances 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 12
- 238000005406 washing Methods 0.000 abstract description 8
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- 239000004033 plastic Substances 0.000 abstract description 4
- 229920003023 plastic Polymers 0.000 abstract description 4
- 239000006185 dispersion Substances 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 239000012209 synthetic fiber Substances 0.000 abstract description 3
- 229920002994 synthetic fiber Polymers 0.000 abstract description 3
- 238000007598 dipping method Methods 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 239000000123 paper Substances 0.000 abstract description 2
- 231100000614 poison Toxicity 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000003440 toxic substance Substances 0.000 abstract description 2
- 239000004599 antimicrobial Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000006866 deterioration Effects 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 238000004898 kneading Methods 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- -1 4-carboxyethyl phenyl Chemical group 0.000 description 12
- 239000002781 deodorant agent Substances 0.000 description 12
- 239000003242 anti bacterial agent Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 5
- 150000002013 dioxins Chemical class 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NWYHVMDKERUNLM-UHFFFAOYSA-N 2,4-dichloro-1-[(2,4-dichlorophenyl)methoxymethyl]benzene Chemical compound ClC1=CC(Cl)=CC=C1COCC1=CC=C(Cl)C=C1Cl NWYHVMDKERUNLM-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- IPELERXCTPOVQF-UHFFFAOYSA-N 1-chloro-4-[(4-chloro-3-methylphenoxy)methoxy]-2-methylbenzene Chemical compound C1=C(Cl)C(C)=CC(OCOC=2C=C(C)C(Cl)=CC=2)=C1 IPELERXCTPOVQF-UHFFFAOYSA-N 0.000 description 2
- COVKSLBAQCJQMS-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenoxy)methoxy]benzene Chemical compound C1=CC(Cl)=CC=C1OCOC1=CC=C(Cl)C=C1 COVKSLBAQCJQMS-UHFFFAOYSA-N 0.000 description 2
- RTZMZAQZRVUVIZ-UHFFFAOYSA-N 2,4-dichloro-1-[(2,4-dichlorophenoxy)methoxy]benzene Chemical compound ClC1=CC(Cl)=CC=C1OCOC1=CC=C(Cl)C=C1Cl RTZMZAQZRVUVIZ-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- DCFGSSAHQAVEBW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)octadecan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH2+]CCC[Si](OC)(OC)OC DCFGSSAHQAVEBW-UHFFFAOYSA-N 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000006286 dichlorobenzyl group Chemical group 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Abstract
Description
この発明は、繊維などの基材に抗菌防臭効果が付与され
た抗菌防臭材料に関する。The present invention relates to an antibacterial and deodorizing material in which a base material such as fiber is imparted with an antibacterial and deodorizing effect.
近年、細菌類、カビ類等の増殖による悪臭、繊維の変色
や脆化等を防いだり、人体に対する皮膚病などの病原菌
を防いだりするため、繊維等の基材に抗菌防臭加工を施
した抗菌防臭材料を用いるようになってきている。特に
、防臭効果に重点が置かれ、衣類や靴下などの防臭加工
をはじめ、高齢化社会への移行による寝たきり老人の衛
生問題等を解消するためにも、抗菌防臭材料が注目され
ている。In recent years, antibacterial and deodorizing treatments have been applied to base materials such as fibers to prevent bad odors, discoloration and embrittlement of fibers caused by the growth of bacteria and mold, and to prevent pathogens such as skin diseases to the human body. Deodorant materials are increasingly being used. In particular, emphasis has been placed on deodorizing effects, and antibacterial and deodorizing materials are attracting attention not only for deodorizing clothing and socks, but also for solving hygiene problems for bedridden elderly due to the transition to an aging society.
ところで、従来の抗菌防臭材料としては、２．４４°−
トリクロロ−２”−ヒドロキシジフェニルエーテルやオ
クタデシル（３−トリメトキシシリルプロピル）アンモ
ニウムクロライドなどの抗菌防臭薬剤が繊維等の基材に
定着されて形成されていたが、２．４．４− トリクロ
ロ−２゛−ヒドロキシジフェニルエーテルは、焼却時に
ダイオキシンが発生ずることが公表され、使用中止とな
った。一方、オクタデシル（３−トリメトキシシリルプ
ロピル）アンモニウムクロライドは、加工時に１２０°
Ｃ以上になると分解し、染色布が変色をおこすと言う問
題がある。
しかも、カチオン性を有しているため、螢光染料などの
アニオン化物とのブロッキングが起こり、抗菌防臭効果
が阻害されると言う傾向があり、家庭洗剤中の螢光染料
によって耐洗濯性が阻害されると言う問題もある。
この発明は、このような事情に鑑みて、焼却時にダイオ
キシン等の有毒物質の発生がなくて安全性が高く、耐洗
濯性に優れ、堅牢度の低下も少なく、かつ、染料等の変
色もない抗菌防臭材料を提供することを目的としている
。By the way, as a conventional antibacterial and deodorizing material, 2.44°-
Antibacterial and deodorizing agents such as trichloro-2''-hydroxydiphenyl ether and octadecyl (3-trimethoxysilylpropyl) ammonium chloride were fixed to base materials such as fibers, but 2.4.4-trichloro-2'' -Hydroxydiphenyl ether was discontinued after it was announced that dioxins were generated when incinerated.On the other hand, octadecyl (3-trimethoxysilylpropyl) ammonium chloride
When the temperature exceeds C, there is a problem that it decomposes and causes discoloration of the dyed cloth. Moreover, because it has cationic properties, it tends to block with anionized substances such as fluorescent dyes, inhibiting its antibacterial and deodorizing effect, and the fluorescent dyes in household detergents inhibit washing resistance. There is also the issue of being exposed. In view of these circumstances, this invention is highly safe as it does not generate toxic substances such as dioxins when incinerated, has excellent washing resistance, has little loss of fastness, and does not cause discoloration of dyes, etc. The purpose is to provide antibacterial and deodorizing materials.
この発明は、このような目的を達成するために、一般式
一般式
Ｘ＝ハロゲン、Ｙ、 Ｚ−−Ｒ，−ＮＨＲ，−Ｃｏｏ
ｌ？、 −０ＲＮＩＩＣＯＣ）ｌｚ （但し、Ｒ＝水素
またはアルキル基）、Ｍ＝−ＣＨｚ−、−ＣＲ２−、−
Ｃ１１２ＣＩ＋２−（０−ＣＩｌＺＣＨ２）、ｌ−〕で
表すれるハロゲン置換ベンジルフェニルエーテル類、ハ
ロゲン置換ビスフェノキシメタン類、ハロゲン置換ビス
フェノキシジエチルエーテル類からなる群より選ばれた
少なくとも１種の抗菌防臭薬剤が、基材に定着されてな
る抗菌防臭材料を要旨としている。In order to achieve such an object, the present invention provides the general formula X = halogen, Y, Z--R, -NHR, -Coo
l? , -0RNIICOC)lz (however, R = hydrogen or alkyl group), M = -CHz-, -CR2-, -
At least one antibacterial and deodorant agent selected from the group consisting of halogen-substituted benzyl phenyl ethers, halogen-substituted bisphenoxymethanes, and halogen-substituted bisphenoxy diethyl ethers represented by C112CI+2-(0-CIlZCH2), l-] , the gist is an antibacterial and deodorizing material that is fixed to a base material.
上記構成により焼却時等にダイオキシンの発生がなくな
るとともに、螢光染料により抗菌防臭効果が阻害されな
くなる。The above structure eliminates the generation of dioxins during incineration, and also prevents the antibacterial and deodorizing effect from being inhibited by the fluorescent dye.
以下に、この発明を、その実施例を参照しつつ詳しく説
明する。
この発明にかかる抗菌防臭材料に用いられる基材として
は、特に限定されないが、例えば、繊維。
紙、布帛、プラスチック材料等が挙げられる。
また、この発明にかかる抗菌防臭材料に用いられる上記
一般式（Ａ）または（Ｂ）で表される抗菌防臭薬剤とし
ては、例えば、２．４−ジクロロフェニル−Ｃ２’、４
’−ジクロロベンジルコエーテル、４−クロロフェニル
−［２’、４’−ジクロロベンジルコエーテル、２．４
−ジクロロフェニル−［４′−ジクロロヘンシル］エー
テル、３−メチル−４−クロロフェニル−［２’、４’
−ジクロロベンジルコエーテル、２−アセチルアミノ−
４−クロロフェニル−［２’、４’−ジクロロヘンシル
］エーテル、４−カポキシメチルフェニル−［２’、４
’−ジクロロベンジルコエーテル、４−カボキシエチル
フエニルー ［２’、４’−ジクロロベンジルコエーテ
ル、２−カポキシメチルフェニル［２“、４′−ジクロ
ロベンジルコエーテル、２−メトキシフェニル−［２’
、４’−ジクロロベンジルコエーテル、２−ヒドロキシ
フェニル−［２’ 、４’−ジクロロベンジル司エーテ
ル、ビス（２，４−ジクロロフェノキシ）メタン、ビス
（４−クロロフェノキシ）メタン、ビス（３−メチル−
４−クロロフェノキシ）メタン、ビス（４−クロロフェ
ノキシ）ジエチルエーテル、ビス（２，４−ジクロロフ
ェノキシ）ジエチルエーテル、ビス（３−メチル−４−
クロロフェノキシ）ジエチルエーテル等が挙げられる。
これらの抗菌防臭薬剤は、特に限定されないが、たとえ
ば、基材が繊維の場合その仕上げ加工において、上記抗
菌防臭薬剤を溶媒または乳化剤で水に乳化分散させて分
散液を作製し、この分散液をパッディング法・浸漬法・
スプレー法などの公知の方法により繊維に定着させる第
１の方法や、合成繊維材料やプラスチック材料に直接内
部に練り込む第２の方法等により基材に定着することが
できる。このうち、−第２の方法では、上記抗菌防臭薬
剤が射出成形機や他の成形機中で溶融した樹脂と均等に
混合されるため、仕上げ加工と異なり、耐洗濯性が数段
良好になる傾向にある。
上記抗菌防臭薬剤の基材への定着量は、０．１〜１０重
量％が望ましく、第１の方法のように付着により定着さ
せる場合には、０．１〜５重量％程度、特に、０．８〜
３重量重量％跡良く、少なく過ぎると抗菌防臭効果が弱
くなり、多すぎると安全性・繊維の風合・堅牢度・加工
単価などの点で少し問題が出てくる。
なお、第１の方法のように付着により定着させる場合、
基材に対する抗菌防臭薬剤の付着量の調整は、処理液濃
度や絞り率の調節により行い、乾燥条件としては、通常
７０〜２００°Ｃで３０秒ないし３０分程度が好ましい
。
また、耐洗濯性をさらに向上させるために、上記抗菌防
臭薬剤と樹脂とを併用するようにしても構わない。この
場合の樹脂としては、たとえば、繊維素反応型樹脂（初
期縮合尿素系樹脂、クリオギザール系樹脂等）、熱硬化
型樹脂（縮合尿素系樹脂、メラミン系樹脂、ウレタン系
樹脂、エポキシ系樹脂等）、熱可塑型樹脂（アクリル系
樹脂。
フェノール系樹脂、酢酸ビニル系樹脂、塩化ビニル系樹
脂、スチレン系樹脂、ポリアミド系樹脂。
ボリエ込チル系樹脂等）などが挙げられる。
なお、これら樹脂のうち、繊維素反応型樹脂、熱硬化型
樹脂を併用すれば、樹脂用触媒により繊維上で強固な皮
膜を形成し、上記抗菌防臭薬剤がマスキングされて、耐
洗濯性がより向上する傾向がある。
さらに、これら樹脂とともに、樹脂加工を目的とした薬
剤、たとえば、柔軟剤、上水剤１防炎剤。
吸水剤、風合調節剤等を併用しても構わない。
（実施例１）
抗菌防臭薬剤として２−ヒドロキシフェニル［２’、４
°−ジクロロベンジルコエーテルの１．８Ｌｆｉｔ％メ
タノール溶液のパッド液を用意し、基材としての綿ブロ
ード＃４０布（精練・漂白済み）をこのパッド液に１デ
イツプしマツグルで１ニツプしてピックアップ５６％に
絞ったのち、ピンテンクーにて乾燥を１０５°ＣＸＩ分
間行い、抗菌防臭布を得た。なお、布への抗菌防臭薬剤
の付着量は、１．０％ｏ、ｗ、ｆ、であった。
（実施例２）
抗菌防臭薬剤としての２−ヒドロキシフェニル−［２°
、４°−ジクロロベンジルコエーテルが１０重量部（以
下、「部」とのみ記す）、ポリオキシエチレン高級アル
コールエーテル（界面活性剤）１０部、ポリオキシエチ
レン誘導体（界面活性剤）５部、ブチルセロソルブ１０
部、水６５部からなる水溶性エマルジョン化物を用意し
、さらに、この水溶性エマルジョン１４部、４０％ジメ
チロールジヒドロキジエチレン尿素樹脂７部、５０％塩
化マグネシウム２．１部、水７６．９部からなるパッド
液を作製した。そして、基材としての綿ブロード＃４０
布（精練・漂白済み）をこのパッド液に１デイツプしマ
ツグルで１ニツプしてピックアップ７３％に絞ったのち
、ピンテンターにて乾燥を１０５°ＣＸＩ分３０秒、キ
ユアリングを１５５°ｃ×１分３０秒行い、抗菌防臭布
を得た。なお、布への抗菌防臭薬剤の付着量は、１．０
％ｏ、ｗ、ｆ、であった。
（実施例３）
抗菌防臭薬剤として２−メトキシフェニル−［２゛。
４゛−ジクロロベンジルコエーテルを用いた以外は、実
施例１と同様にして抗菌防臭布を得た。
（実施例４）
抗菌防臭薬剤として２．４−ジクロロフェニル［２’、
４“−ジクロロベンジル１エーテルを用いた以外は、実
施例１と同様にして抗菌防臭布を得た。
（実施例５）
抗菌防臭薬剤として４−クロロフェニル−［２”、４−
ジクロロベンジル１エーテルを用いた以外は、実施例１
と同様にして抗菌防臭布を得た。
（実施例６）
抗菌防臭薬剤として２．４−ジクロロフェニル［４゛−
クロロベンジルコエーテルを用いた以外は、実施例１と
同様にして抗菌防臭布を得た。
（実施例７）
抗菌防臭薬剤として２，４．ジクロロフェニル［２°−
クロロベンジルコエーテルを用いた以外は、実施例１と
同様にして抗菌防臭布を得た。
（実施例８）
抗菌防臭薬剤として３−メチル−４−クロロフェニル−
［２’、４’−ジクロロベンジル］エーテルヲ用いた以
外は、実施例１と同様にして抗菌防臭布を得た。
（実施例９）
抗菌防臭薬剤としてビス（４−クロロフェノキシ）メタ
ンを用いた以外は、実施例１と同様にして抗菌防臭布を
得た。
（実施例１０）
抗菌防臭薬剤としてビス（２，４−ジクロロフェノキシ
）メタンを用いた以外は、実施例１と同様にして抗菌防
臭布を得た。
（実施例１１）
抗菌防臭薬剤としてビス（３−メチル−４−クロロフェ
ノキシ）メタンを用いた以外は、実施例１と同様４こし
て抗菌防臭布を得た。
（実施例１２）
抗菌防臭薬剤として２−アセチルアミノ−４−クロロフ
ェニル−［２’ 、４’ −’；ジクロロンシル１エー
テルを用いた以外は、実施例１と同様にして抗菌防臭布
を得た。
（実施例１３）
抗菌防臭薬剤として４−カルボキシルメチルフェニル−
［２′、４“−ジクロロヘンシル］エーテルを用いた以
外は、実施例１と同様にして抗菌防臭布を得た。
（実施例１４）
抗菌防臭薬剤として４−カルボキシルエチルフェニル−
［２’、４’−ジクロロベンジル］エーテルを用いた以
外は、実施例１と同様にして抗菌防臭布を得た。
（実施例１５）
抗菌防臭薬剤として２−カルボキシルメチルフェニル−
［２’、４’−ジクロロベンジル］エーテルを用いた以
外は、実施例１と同様にして抗菌防臭布を得た。
（実施例１６）
抗菌防臭薬剤としてビス（４−クロロフェノキシ）ジエ
チルエーテルを用いた以外は、実施例１と同様にして抗
菌防臭布を得た。
（実施例１７）
抗菌防臭薬剤としてビス（３−メチル−４−クロロフェ
ノキシ）ジエチルエーテルを用いた以外は、実施例１と
同様にして抗菌防臭布を得た。
（比較例１）
抗菌防臭薬剤として２，４．４ − トリクロロ−２′
ヒドロキシジフエニルエーテルを用いた以外は、実施例
１と同様にして抗菌防臭布を得た。
（比較例２）
抗菌防臭薬剤としてオクタデシル（３−４トリメトキシ
シリルプロピル）アンモニウムクロライドを用いた以外
は、実施例１と同様にして抗菌防臭布を得た。
繊維製品衛生加工協議会指定の方法に基づいて上記の実
施例１〜１７および比較例１．２で得られた抗菌防臭布
のそれぞれの抗菌性試験を実施した。
その結果を第１表に示す。
第１表
第１表にみるように、実施例のものは、何れの布も抗菌
防臭効果があり、しかも、薬剤による着色、変色、臭気
なども全くなかった。なお、実施例２において得られた
抗菌防臭布について、５回洗濯後のハローテスト法及び
菌数測定法による抗菌試験を実施したところ、ハローテ
スト法においては、ハロー幅が４鴫で判定が○、菌数測
定法においては、増減値差が３．３６で判定が○であり
、耐洗濯性も確認できた。
この発明にかかる抗菌防臭材料は上記の実施例に限定さ
れない。たとえば、上記の実施例では、基材が綿ブロー
ド布であったが、他の天然繊維布でもよいし、合成繊維
布でも構わない。また、上記の実施例では、抗菌防臭薬
剤が１種類しか用いられていないが、２種類以上混合し
て用いるようにしても構わない。The present invention will be described in detail below with reference to examples thereof. The base material used in the antibacterial and deodorant material according to the present invention is not particularly limited, but includes, for example, fiber. Examples include paper, cloth, plastic materials, etc. Furthermore, the antibacterial and deodorizing agent represented by the above general formula (A) or (B) used in the antibacterial and deodorizing material according to the present invention includes, for example, 2,4-dichlorophenyl-C2', 4
'-dichlorobenzyl coether, 4-chlorophenyl-[2',4'-dichlorobenzyl coether, 2.4
-dichlorophenyl-[4'-dichlorohensyl]ether, 3-methyl-4-chlorophenyl-[2', 4'
-dichlorobenzyl coether, 2-acetylamino-
4-chlorophenyl-[2',4'-dichlorohensyl]ether, 4-capoxymethylphenyl-[2',4
'-dichlorobenzyl coether, 4-carboxyethyl phenyl [2', 4'-dichlorobenzyl coether, 2-capoxymethyl phenyl [2'', 4'-dichlorobenzyl coether, 2-methoxyphenyl] 2'
, 4'-dichlorobenzyl coether, 2-hydroxyphenyl-[2',4'-dichlorobenzyl coether, bis(2,4-dichlorophenoxy)methane, bis(4-chlorophenoxy)methane, bis(3- Methyl-
4-chlorophenoxy) methane, bis(4-chlorophenoxy) diethyl ether, bis(2,4-dichlorophenoxy) diethyl ether, bis(3-methyl-4-
(chlorophenoxy) diethyl ether and the like. These antibacterial and deodorizing agents are not particularly limited, but for example, when the base material is fiber, in the finishing process, the above-mentioned antibacterial and deodorant agents are emulsified and dispersed in water using a solvent or emulsifier to prepare a dispersion, and this dispersion is Padding method, dipping method,
It can be fixed to the base material by a first method in which it is fixed on fibers by a known method such as a spray method, or a second method in which it is kneaded directly into a synthetic fiber material or plastic material. Among these, - in the second method, the antibacterial and deodorizing agent is evenly mixed with the molten resin in the injection molding machine or other molding machines, so unlike finishing processing, the washing resistance is much better. There is a tendency. The amount of the antibacterial and deodorizing agent fixed on the base material is preferably 0.1 to 10% by weight, and when it is fixed by adhesion as in the first method, it is about 0.1 to 5% by weight, especially 0.1 to 10% by weight. .8～
3% by weight.If it is too low, the antibacterial and deodorizing effect will be weakened, and if it is too high, there will be some problems in terms of safety, fiber texture, fastness, processing cost, etc. In addition, when fixing by adhesion as in the first method,
The amount of the antibacterial and deodorant agent adhered to the substrate is adjusted by adjusting the concentration of the treatment liquid and the squeezing rate, and the drying conditions are usually preferably 70 to 200°C for about 30 seconds to 30 minutes. Moreover, in order to further improve washing resistance, the above-mentioned antibacterial and deodorizing agent and resin may be used together. In this case, resins include, for example, cellulose-reactive resins (initial condensed urea resins, cryogysal resins, etc.), thermosetting resins (condensed urea resins, melamine resins, urethane resins, epoxy resins, etc.). ), thermoplastic resins (acrylic resins, phenolic resins, vinyl acetate resins, vinyl chloride resins, styrene resins, polyamide resins, chilled resins containing polyethylene, etc.). Of these resins, if cellulose-reactive resins and thermosetting resins are used together, the resin catalyst will form a strong film on the fibers, masking the antibacterial and deodorizing agent, and improving washing resistance. There is a tendency to improve. In addition to these resins, there are also agents for resin processing, such as softeners, water-cleaning agents, and flame retardants. A water absorbing agent, a texture controlling agent, etc. may be used in combination. (Example 1) 2-hydroxyphenyl [2',4
Prepare a pad solution of 1.8L fit% methanol solution of °-dichlorobenzyl coether, dip a #40 cotton broad cloth (scoured and bleached) as a base material in this pad solution for 1 time, pick it up by nipping it with a Matuguru. After narrowing down to 56%, it was dried using a pintoku for 105° CXI minutes to obtain an antibacterial and deodorizing cloth. The amount of the antibacterial and deodorant agent adhered to the cloth was 1.0% o, w, f. (Example 2) 2-Hydroxyphenyl-[2° as an antibacterial and deodorizing agent
, 10 parts by weight of 4°-dichlorobenzyl coether (hereinafter referred to as "parts"), 10 parts of polyoxyethylene higher alcohol ether (surfactant), 5 parts of polyoxyethylene derivative (surfactant), butyl cellosolve 10
Prepare a water-soluble emulsion consisting of 65 parts of water, 14 parts of this water-soluble emulsion, 7 parts of 40% dimethylol dihydroxy ethylene urea resin, 2.1 parts of 50% magnesium chloride, and 76.9 parts of water. A pad solution consisting of And cotton broad #40 as base material
Dip a cloth (scoured and bleached) into this pad solution for 1 day, squeeze it with a Matuguru once to reduce the pickup to 73%, then dry with a pin tenter at 105°C for 30 seconds and cure at 155°C for 1 minute and 30 minutes. After a few seconds, an antibacterial and deodorizing cloth was obtained. In addition, the amount of antibacterial and deodorizing agent attached to the cloth is 1.0
%o, w, f. (Example 3) 2-methoxyphenyl-[2゛] as an antibacterial and deodorizing agent. An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that 4'-dichlorobenzyl coether was used. (Example 4) 2,4-dichlorophenyl [2',
An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that 4"-dichlorobenzyl 1 ether was used. (Example 5) 4-chlorophenyl-[2",4-
Example 1 except that dichlorobenzyl 1 ether was used.
An antibacterial and deodorizing cloth was obtained in the same manner. (Example 6) 2,4-dichlorophenyl[4゛-
An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that chlorobenzyl coether was used. (Example 7) 2, 4 as an antibacterial and deodorizing agent. Dichlorophenyl [2°-
An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that chlorobenzyl coether was used. (Example 8) 3-Methyl-4-chlorophenyl- as an antibacterial and deodorant agent
An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1, except that [2',4'-dichlorobenzyl]ether was used. (Example 9) An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1, except that bis(4-chlorophenoxy)methane was used as the antibacterial and deodorizing agent. (Example 10) An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1, except that bis(2,4-dichlorophenoxy)methane was used as the antibacterial and deodorizing agent. (Example 11) An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that bis(3-methyl-4-chlorophenoxy)methane was used as the antibacterial and deodorizing agent. (Example 12) An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1, except that 2-acetylamino-4-chlorophenyl-[2',4'-';dichloroncil 1 ether was used as the antibacterial and deodorant agent. . (Example 13) 4-Carboxylmethylphenyl- as an antibacterial and deodorant agent
An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that [2',4''-dichlorohensyl]ether was used. (Example 14) 4-Carboxylethylphenyl- was used as an antibacterial and deodorizing agent.
An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that [2',4'-dichlorobenzyl]ether was used. (Example 15) 2-carboxylmethylphenyl- as an antibacterial and deodorant agent
An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that [2',4'-dichlorobenzyl]ether was used. (Example 16) An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1, except that bis(4-chlorophenoxy) diethyl ether was used as the antibacterial and deodorizing agent. (Example 17) An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1, except that bis(3-methyl-4-chlorophenoxy) diethyl ether was used as the antibacterial and deodorizing agent. (Comparative Example 1) 2,4.4-trichloro-2' as an antibacterial and deodorant agent
An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1 except that hydroxydiphenyl ether was used. (Comparative Example 2) An antibacterial and deodorizing cloth was obtained in the same manner as in Example 1, except that octadecyl (3-4 trimethoxysilylpropyl) ammonium chloride was used as the antibacterial and deodorizing agent. The antibacterial properties of the antibacterial and deodorizing fabrics obtained in Examples 1 to 17 and Comparative Examples 1.2 above were tested based on the method specified by the Textile Sanitation Processing Council. The results are shown in Table 1. As shown in Table 1, all of the fabrics of the Examples had antibacterial and deodorizing effects, and were free from any chemical-induced coloring, discoloration, or odor. In addition, when the antibacterial and deodorizing cloth obtained in Example 2 was subjected to an antibacterial test using the halo test method and the bacteria counting method after being washed five times, in the halo test method, the halo width was 4 squares and the judgment was ○. In the bacterial count measurement method, the difference in increase/decrease value was 3.36, giving a rating of ○, and washing resistance was also confirmed. The antibacterial and deodorant material according to the present invention is not limited to the above embodiments. For example, in the above embodiments, the base material was a broad cotton cloth, but it may be any other natural fiber cloth or synthetic fiber cloth. Further, in the above embodiment, only one type of antibacterial and deodorizing agent is used, but a mixture of two or more types may be used.
この発明にかかる抗菌防臭材料は、以上のように構成さ
れているので、抗菌防臭効果を備えていることは勿論の
こと、焼却時等にダイオキシンの発生がな（非常に安全
なものである。また、螢光染料により抗菌防臭効果が阻
害されないので、耐洗濯性に優れている。Since the antibacterial and deodorizing material according to the present invention is constructed as described above, it not only has an antibacterial and deodorizing effect, but also does not generate dioxins when incinerated (it is extremely safe). Furthermore, since the antibacterial and deodorizing effect is not inhibited by the fluorescent dye, it has excellent washing resistance.
Claims (1)
ロゲン、Ｙ、Ｚ＝−Ｒ、−ＮＨＲ、−ＣＯＯＲ、−ＯＲ
、−ＮＨＣＯＣＨ＿３（但し、Ｒ＝水素またはアルキル
基）Ｍ＝−ＣＨ＿２、−ＣＲ＿２−、−ＣＨ＿２ＣＨ＿
２−（Ｏ−ＣＨ＿２ＣＨ＿２）＿ｎ−〕で表されるハロ
ゲン置換ベンジルフェニルエーテル類、ハロゲン置換ビ
スフェノキシメタン類、ハロゲン置換ビスフェノキシジ
エチルエーテル類からなる群より選ばれた少なくとも１
種の抗菌防臭薬剤が、基材に定着されてなる抗菌防臭材
料。(1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼...(A) Or, General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼...(B) [Formula (A), (B) Medium, m, n=0 or integer, X=halogen, Y, Z=-R, -NHR, -COOR, -OR
, -NHCOCH_3 (where R = hydrogen or alkyl group) M = -CH_2, -CR_2-, -CH_2CH_
At least one selected from the group consisting of halogen-substituted benzyl phenyl ethers, halogen-substituted bisphenoxymethanes, and halogen-substituted bisphenoxy diethyl ethers represented by 2-(O-CH_2CH_2)_n-]
An antibacterial and deodorizing material in which a seed antibacterial and deodorizing agent is fixed to a base material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1183005A JPH0348603A (en) | 1989-07-14 | 1989-07-14 | Antimicrobial and deodorizing material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1183005A JPH0348603A (en) | 1989-07-14 | 1989-07-14 | Antimicrobial and deodorizing material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0348603A true JPH0348603A (en) | 1991-03-01 |
Family
ID=16128082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1183005A Pending JPH0348603A (en) | 1989-07-14 | 1989-07-14 | Antimicrobial and deodorizing material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0348603A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6482985B1 (en) * | 2001-12-03 | 2002-11-19 | Eastman Kodak Company | 2-benzyloxy-5-halo-acylanilide compounds and method of using them |
| JP2005007345A (en) * | 2003-06-20 | 2005-01-13 | Matsushita Electric Ind Co Ltd | Functional filter and its manufacturing method |
| US7547802B2 (en) * | 2001-06-12 | 2009-06-16 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7605181B2 (en) | 2003-02-13 | 2009-10-20 | Wellstat Therapeutics Orporation | Method for the treatment of metabolic disorders |
-
1989
- 1989-07-14 JP JP1183005A patent/JPH0348603A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7547802B2 (en) * | 2001-06-12 | 2009-06-16 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| JP2009227690A (en) * | 2001-06-12 | 2009-10-08 | Wellstat Therapeutics Corp | Compound for treating metabolic disorder |
| RU2502723C2 (en) * | 2001-06-12 | 2013-12-27 | Веллстат Терапьютикс Корпорейшн | Compounds for treating metabolic diseases |
| US6482985B1 (en) * | 2001-12-03 | 2002-11-19 | Eastman Kodak Company | 2-benzyloxy-5-halo-acylanilide compounds and method of using them |
| US7605181B2 (en) | 2003-02-13 | 2009-10-20 | Wellstat Therapeutics Orporation | Method for the treatment of metabolic disorders |
| US7615575B2 (en) | 2003-02-13 | 2009-11-10 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US7932290B2 (en) | 2003-02-13 | 2011-04-26 | Wellstat Biologics Corporation | Method for the treatment of metabolic disorders |
| JP2005007345A (en) * | 2003-06-20 | 2005-01-13 | Matsushita Electric Ind Co Ltd | Functional filter and its manufacturing method |
| JP4590832B2 (en) * | 2003-06-20 | 2010-12-01 | パナソニック株式会社 | Treatment liquid and functional filter and method and apparatus for manufacturing the same |
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