KR100330274B1 - Synthesis and application of low temperature reactive antimicrobial agents for cellulosic materials - Google Patents
Synthesis and application of low temperature reactive antimicrobial agents for cellulosic materials Download PDFInfo
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Abstract
본 발명은 각종 용도에 있어서 항균첨가제로서 뿐만 아니라 면(레이온), 양모, 아세테이트, 폴리에스테르/면 혹은 폴리에스테르/레이온의 혼방 혹은 교직물 등에 적용이 가능하며 각종세제에 대해 세탁내구성을 가진 저온 섬유소 반응형의 고정형항균제에 관한 것이다.The present invention can be applied not only as an antimicrobial additive in various applications but also as a blend of cotton (rayon), wool, acetate, polyester / cotton or polyester / rayon, or a textile, and a low temperature cellulose reaction having laundry durability for various detergents. It relates to a fixed type antimicrobial agent.
본 발명의 항균제는 알릴클로리드와 디알킬아민으로부터 합성된 디알킬디알릴암모늄클로리드(Ⅰ )를 디알릴아민과 반응시켜 디알킬디알릴암모늄클로리드/디알릴아민 공중합체(Ⅲ)을 합성하고, 이 공중합체와 시아누릭클로리드(Cyanuric chloride)를 반응시켜 최종항균물질인 중합체(Ⅳ)를 얻으며 이 항균물질을 이용하여 패드-배치(Pad-Batch)법이나 패드-드라이(Pad-dry)법으로 직물을 저온처리함으로써 직물의 품질과 세탁내구성을 유지하면서 항균작용을 할 수 있는 저온섬유소 반응형의 고정형항균제를 제공함을 발명의 특징으로 한다.The antimicrobial agent of the present invention synthesizes a dialkyldiallylammonium chloride / diallylamine copolymer (III) by reacting dialkyldiallylammonium chloride (I) synthesized from allyl chloride and dialkylamine with diallylamine. The copolymer is reacted with cyanuric chloride to obtain the final antimicrobial polymer (IV). The antimicrobial material is used for the pad-batch or pad-dry method. It is a feature of the invention to provide a low temperature fiber reactive type fixed antimicrobial agent capable of antibacterial action while maintaining the quality of the fabric and washing durability by low temperature treatment of the fabric.
Description
본 발명은 직물에 항균가공성을 적용시키는 고정형 유기항균제 제조에 관한 것으로, 보다 상세하게는 각종 용도에 있어서 항균첨가제로서 뿐만 아니라 면(레이온), 양모, 아세테이트, 폴리에스테르/면 혹은 폴리에스테르/레이온의 혼방 혹은 교직물 등에 적용이 가능하며, 각종세제에 대해 세탁내구성을 가진 저온 반응형의 고정형항균제와 그 제조방법에 관한 것이다.FIELD OF THE INVENTION The present invention relates to the preparation of fixed organic antimicrobial agents for applying antimicrobial properties to fabrics, and more particularly to the use of cotton (rayon), wool, acetate, polyester / cotton or polyester / rayon as an antimicrobial additive in various applications. Applicable to blends or fabrics, etc., and relates to a low-temperature reaction type fixed antimicrobial agent having a laundry durability for various detergents and a method of manufacturing the same.
최근 생활환경이 개선됨에 따라 과거 기능성만이 강조되던 제품으로부터 위생, 쾌적, 건강 지향적인 제품을 선호하게 되어, 섬유공업에 있어서도 항균가공약제를 이용한 항균가공의 중요성이 부각되고 있다. 항균가공제는 일반적으로 유기 및 무기계로 구분이 된다. 무기계는 자체로서 섬유에의 흡착력이 없기 때문에 합성섬유의 원사에 혼입하게 되며 천연섬유인 경우에는 바인더를 이용하여 섬유표면에 고착시키는 방법을 사용하지만 촉감의 저하로 인해 바람직하지 못한 결점이 있다. 유기계는 확산형과 고정형으로 다시 구분되는데 확산형은 무기계와 마찬가지로 바인더를 필요로 하게되고, 인체에 흡수될 경우 유해성에 대한 논란이 있을 수 있다. 고정형 유기 항균제는 섬유와 반응하여 항균성능을 나타내게 되어 무기계 및 확산형 유기항균제에서와 같은 문제를 없앨 수 있다. 현재 시판중인 대부분의 고정형 유기항균가공제는 4급 암모늄염계로서 항균력은 뛰어나지만 세제의 종류에 따라 세탁후 항균제가 세척되어 버림으로써 세탁내구성에 문제가 있었고, 또한 이 항균가공제를 섬유에 반응시킬 때 고온에서 처리하게 되어 섬유품질을 저하시키는 원인이 되었다.Recently, as the living environment is improved, hygiene, comfort, and health-oriented products are favored from products that were emphasized only in the past, and the importance of antimicrobial processing using antimicrobial processing agents in the textile industry has been highlighted. Antimicrobial agents are generally divided into organic and inorganic. Inorganic systems are incorporated into yarns of synthetic fibers because they do not have adsorptive power to fibers, and in the case of natural fibers, a binder is used to fix the fiber to the surface of the fiber. The organic type is divided into a diffusion type and a fixed type. The diffusion type requires a binder like the inorganic type, and there may be a controversy about the harmfulness when absorbed by the human body. The fixed organic antimicrobial agent reacts with the fiber to exhibit antimicrobial performance, thereby eliminating the problems as in the inorganic and diffusion organic antimicrobial agents. Most of the fixed organic antimicrobial agents currently on the market are quaternary ammonium salts and have excellent antibacterial properties. However, depending on the type of detergent, the antimicrobial agents were washed after washing, causing problems in laundry durability. Treatment caused a decrease in fiber quality.
본 발명은 이러한 문제점을 해소하기 위한 것으로 각종용도의 항균첨가제로서 뿐만 아니라 면(레이온), 양모, 아세테이트, 폴리에스테르/면 혹은 폴리에스테르/레이온의 혼방 혹은 교직물 등에 적용하여 촉감저하나 인체유해없이 고정형 유기항균제의 세탁내구성을 획기적으로 상승시키면서 직물의 품질을 유지하고 항균처리할 수 있도록 항균가공제를 직물에 패딩후 저온에서 처리하는 것을 발명의 목적으로 한다.The present invention is to solve this problem, as well as antimicrobial additives of various uses as well as cotton (rayon), wool, acetate, polyester / cotton or blends or blends of polyester / rayon, etc. The purpose of the invention is to treat the antimicrobial agent at low temperature after padding the fabric to maintain the quality of the fabric and to antibacterial treatment while significantly increasing the durability of the organic antimicrobial agent.
이와같은 목적을 달성하기 위하여 알릴클로리드와 디알킬아민으로부터 합성된 디알킬디알릴암모늄클로리드(Ⅰ )를 디알릴아민(Ⅱ)과 반응시켜 공중합물(Ⅲ)을 합성하고, 이 공중합물(Ⅲ)과 시아누릭클로리드(Cyanuric chloride)와 반응시켜 최종항균물질인 중합체 (Ⅳ)를 얻으며 또한 이 항균물질(Ⅳ)을 이용하여 패드-배치(Pad-Batch)법이나 패드-드라이(Pad-dry)법으로 저온처리함으로써 직물의 품질을 유지시키는 저온섬유소 반응형의 고정형 항균가공제를 제공함을 발명의 특징으로 한다.In order to achieve this object, a copolymer (III) is synthesized by reacting diallylamine (II) with diallylamine (II) synthesized from allyl chloride and dialkylamine. Ⅲ) and cyanuric chloride to obtain the final antimicrobial polymer (IV), and using this antimicrobial material (Pad-Batch) or Pad-Dry It is a feature of the invention to provide a low temperature fiber reactive fixed antimicrobial agent that maintains the quality of the fabric by low temperature treatment by dry method.
1. 항균제의 합성방법1. Synthesis of Antimicrobial Agents
알릴클로리드와 디알킬아민으로부터 합성된 디알킬디알릴암모늄클로리드 단량체(Ⅰ )와 디알릴아민(Ⅱ )을 하기 반응식과 같이 공중합시켜 디알킬디알릴암모늄클로리드/디알릴아민 공중합물(Ⅲ)을 합성하며, 이 공중합물과 시아누릭클로리드 (Cyanuric Chloride)를 반응시켜 항균물질인 중합체 (Ⅳ)를 얻는다.The dialkyldiallylammonium chloride / diallylamine copolymer (III) is copolymerized by dialkyldiallylammonium chloride monomer (I) synthesized from allyl chloride and dialkylamine as shown in the following scheme. ) Is synthesized, and the copolymer is reacted with cyanuric chloride to obtain an antimicrobial polymer (IV).
상기식에서 치환기 R1, R2는 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실기를 나타내고, 디알킬디알릴암모늄클로리드(Ⅰ)와 디알릴아민(Ⅱ)의 공중합체(Ⅲ)에 있어서 m/n의 비는 0.1∼2.0의 값을 가지며 중합체 (Ⅳ)에 있어서 m/n의 비는 0.1∼15.0사이의값을 갖는다.In the above formula, the substituents R 1 and R 2 represent methyl, ethyl, propyl, butyl, pentyl and hexyl groups, and m in the copolymer (III) of the dialkyl diallyl ammonium chloride (I) and diallylamine (II) The ratio of / n has a value of 0.1 to 2.0 and the ratio of m / n in the polymer (IV) has a value of 0.1 to 15.0.
<실시예><Example>
1)디알킬디알릴암모늄클로리드(Ⅰ )와 디알릴아민(Ⅱ)의 공중합1) Copolymerization of dialkyl diallyl ammonium chloride (I) and diallylamine (II)
디알릴아민(Ⅱ)을 소량의 염산수용액으로 가용화시킨 후 디알킬디알릴암모늄클로리드(Ⅰ ) 1몰에 대해 0.1몰의 비율로 혼합하여 총 단량체의 농도가 30%가 되도록 한다. 이 단량체 용액에 단량체 대비 0.5wt%의 암모늄 퍼옥소디설페이트 (ammonium peroxodisulfate)를 개시제로 첨가한 후 용기내를 질소로 치환하여 밀봉한 다음 60℃에서 6시간 동안 반응을 시킨다. 반응 종료후 내용물을 아세톤에 재침전시켜 디알킬디알릴암모늄클로디드/디알릴아민 공중합물(Ⅲ)을 얻는다.Solubilizing diallylamine (II) with a small amount of aqueous hydrochloric acid solution is mixed at a ratio of 0.1 mole to 1 mole of dialkyldiallylammonium chloride (I) so that the total monomer concentration is 30%. To this monomer solution, 0.5% by weight of ammonium peroxodisulfate (ammonium peroxodisulfate) relative to the monomer is added as an initiator, the container is replaced with nitrogen, sealed and reacted at 60 ° C. for 6 hours. After completion of the reaction, the contents are reprecipitated in acetone to obtain dialkyldiallylammonium chloride / diallylamine copolymer (III).
2)디알킬디알릴암모늄클로리드/디알릴아민 공중합물(Ⅲ)과 시아누릭클로리드 (cyanuric chloride)와의 반응2) Reaction of dialkyldiallylammonium chloride / diallylamine copolymer (III) with cyanuric chloride
디알킬디알릴암모늄클로리드/디알릴아민 공중합물(Ⅲ)을 10% 수용액으로 한 후 공중합물 내의 디알릴아민 몰수의 1/2에 상당하는 탄산나트륨을 첨가하여 온도를 0∼5℃로 냉각시킨다. 한편으로 0℃로 냉각된 아세톤에 공중합물 내의 디알릴아민의 몰수에 상당하는 시아누릭클로리드(Cyanuric chloride)를 용해시켜 1%용액을 만든 후, 이를 앞의 디알킬디알릴암모늄클로이드/디알릴아민 공중합물(Ⅲ)용액에 30분 동안 서서히 적하시킨다. 시아누릭클로리드(Cyanuric chloride)의 첨가가 끝난 후 반응이 진행됨에 따라 생성되는 염산은 2M의 탄산나트륨 수용액으로 중성 내지 약산성(pH 6정도)으로 pH를 유지해주면서 더 이상의 pH 변화가 없을 때까지 3시간정도 반응 후, 반응용액을 비용매인 아세톤에 침전시킨다. 침전된 반응물을 아세톤으로 수회 세척하여 미반응 시아누릭클로리드(Cyanuric chloride)를 제거한 후 상온에서 진공건조하여 최종 항균물질인 중합체 (Ⅳ)를 얻는다.The dialkyldiallylammonium chloride / diallylamine copolymer (III) is made into a 10% aqueous solution, and sodium carbonate corresponding to 1/2 of the number of moles of diallylamine in the copolymer is added to cool the temperature to 0 to 5 ° C. . On the other hand, a 1% solution is prepared by dissolving cyanuric chloride corresponding to the number of moles of diallylamine in the copolymer in acetone cooled to 0 ° C., and then dialkyldiallylammonium chloride / di It is slowly added dropwise to the allylamine copolymer (III) solution for 30 minutes. After the addition of cyanuric chloride, the hydrochloric acid produced as the reaction proceeds is maintained in neutral to weak acidity (pH 6) with 2M aqueous sodium carbonate solution for 3 hours until no further pH changes. After moderate reaction, the reaction solution is precipitated in acetone, which is a nonsolvent. The precipitated reactant was washed several times with acetone to remove unreacted cyanuric chloride and dried in vacuo at room temperature to obtain the final antimicrobial polymer (IV).
2. 직물에의 처리방법2. Treatment method to fabric
항균가공제인 중합체(Ⅳ) 0.3∼3wt% 수용액에 대상직물(면, 레이온, 아세테이트, 양모, 폴리에스테르/면 혹은 폴리에스테르/레이온의 혼방 혹은 교직물 등)을 침지하여 적절한 웨트 픽업률(wet pick-up) 60∼100wt%로 압착(spueezing)한다. 압착된 시료는 35∼45℃정도에서 6시간 이상 방치하는 패드-배치(Pad-batch)법으로 처리하거나 90∼110℃부근의 온도에서 3∼5분간 건조하는 패드-드라이(Pad-dry)법으로 처리함으로써 중합체 (Ⅳ)의 항균가공제가 섬유상에 고착된다. 항균제 처리는 정련된 직물상태에서 처리하거나 혹은 염색후 가공공정에서 처리하여도 항균성에는 큰 차이가 없다.An appropriate wet pick-up rate is obtained by immersing the target fabric (cotton, rayon, acetate, wool, polyester / cotton, or a blend of polyester / rayon or a textile) in an aqueous solution of 0.3 to 3 wt% of an antimicrobial agent. up) Squeeze at 60-100 wt%. The compressed sample is treated with a pad-batch method that is left at about 35 to 45 ° C. for 6 hours or more, or dried for 3 to 5 minutes at a temperature near 90 to 110 ° C. The antimicrobial agent of polymer (IV) is fixed on the fiber by treating with. Antimicrobial treatment does not show any significant difference in antimicrobial activity even when processed in refined fabrics or processed after dyeing.
<실시예 1><Example 1>
면직물을 R1, R2가 메틸로 치환된 중합체(Ⅳ)의 항균가공제 1.0% 수용액으로 65%의 픽업(Pick-up)율로 패딩한 후 40℃에서 6시간 방치한 후 수세한다.The cotton fabric is padded with 1.0% aqueous solution of antimicrobial agent of polymer (IV) in which R 1 and R 2 are substituted with methyl, and then padded at a pick-up rate of 65%, followed by washing at 40 ° C. for 6 hours.
세탁내구성 : 가공된 면직물은 쉐이크 플라스크(Shake flask)시험에서 시험공시균인 스테필로코커스 아우레우스(Staphylococcus aureus) 및 클렙시엘라 뉴모니아(Klebsiella pneumoniae)에 대해 100%의 감균율을 나타내며, KS S 430 A-1법에준하여 음이온계 세제를 사용하여 50회 세탁한 후에도 70%이상의 감균율을 나타낸다.Wash Durability: The processed cotton fabric shows 100% susceptibility to the test bacteria Staphylococcus aureus and Klebsiella pneumoniae in the shake flask test. In accordance with KS S 430 A-1 method, even after washing 50 times using an anionic detergent, it shows a sterilization rate of 70% or more.
<실시예 2><Example 2>
면직물을 R1, R2가 메틸로 치환된 중합체(Ⅳ)의 항균가공제 1.0% 수용액에서 65%의 픽업(Pick-up)율로 패딩한 후 100℃에서 4분간 건조 및 열처리한 후 수세한다.The cotton fabric is padded with a pick-up rate of 65% in a 1.0% aqueous solution of an antimicrobial agent of polymer (IV) in which R 1 and R 2 are substituted with methyl, followed by drying and heat treatment at 100 ° C. for 4 minutes, followed by washing with water.
세탁내구성 : 가공된 면직물은 쉐이크 플라스크(Shake flask)시험에서 시험공시균인 스테필로코커스 아우레우스(Staphylococcus aureus) 및 클렙시엘라 뉴모니아 (Kle-bsiella pneumoniae)에 대해 100%의 감균율을 나타내며, KS S 430 A-1법에 준하여 음이온계 세제를 사용하여 50회 세탁한 후에도 90%이상의 감균율을 나타낸다.Wash Durability: Processed cotton fabrics were 100% tested for shake flask test against Staphylococcus aureus and Kle-bsiella pneumoniae. In accordance with the KS S 430 A-1 method, even after washing 50 times using an anionic detergent shows a sterilization rate of more than 90%.
본 발명에서의 항균처리방법은 바인더를 사용하지 아니하여 인체촉감의 저하가 없고, 확산형이 아닌 고정형 유기 항균제를 사용하여 인체에 유해할 염려가 없을 뿐 아니라 항균가공제를 40℃의 낮은 온도에서 패드-배치법으로 직물에 처리하였을 경우 50회 세탁후에도 70% 이상의 감균율을 나타내고, 100℃의 비교적 낮은 온도에서 패드-드라이법으로 직물에 처리하였을 경우에는 50회 세탁후에도 90%이상의 감균율을 나타냄으로써 고온처리에 의한 직물의 품질손상 없이 높은 세탁내구성을 얻을 수 있다.In the present invention, the antimicrobial treatment method does not have a deterioration of the human feel without using a binder, and there is no fear of harm to the human body by using a fixed organic antimicrobial agent, which is not a diffusion type. -When treated to fabric by batch method, it shows 70% or more sterilization rate even after 50 times washing, and when it is treated to fabric by pad-dry method at relatively low temperature of 100 ℃, it shows more than 90% after 50 times washing. High washing durability can be obtained without damaging the quality of the fabric by high temperature treatment.
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JPH10158108A (en) * | 1996-11-27 | 1998-06-16 | Kao Corp | Prevention of sliminess in bathtub working for 24 hours |
JPH10237763A (en) * | 1997-02-20 | 1998-09-08 | Senka Kk | Antimicrobial agent for treating fiber |
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