KR100821896B1 - Antibacterail acid dyes containing silver and a method of preparing the same and antibacterial fiber thereby - Google Patents
Antibacterail acid dyes containing silver and a method of preparing the same and antibacterial fiber thereby Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/022—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring the heterocyclic ring being alternatively specified
- C09B62/024—Anthracene dyes
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
- D06P1/40—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes using acid dyes without azo groups
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- Textile Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
본 발명은 강력한 항균성 반응기로서 은 함유 설폰아미드계 항균제에 염료 중간체가 결합되어 하기 화학식 1의 구조를 갖는 은 함유 항균 산성 염료 및 그의 제조방법에 관한 것이다.The present invention relates to a silver-containing antimicrobial acid dye having a structure represented by the following formula (1) by binding a dye intermediate to a silver-containing sulfonamide-based antimicrobial agent as a strong antimicrobial reactor, and a method for preparing the same.
(화학식 1)(Formula 1)
(상기식에서, R은 SO3H 또는 SO3Na이다)(Wherein R is SO 3 H or SO 3 Na)
본 발명의 은 함유 항균 산성 염료 화합물은 청색을 갖추고 있어 혼합시 다양한 색상을 발현하고, 이를 이용하여 섬유를 염색하면 강력한 항균성을 나타내어 미생물의 서식이나 증식을 억제하여 전염성질환 예방, 악취예방, 섬유의 오염과 취화를 방지할 수 있는 기능성 항균 섬유 제품을 제조할 수 있다.The silver-containing antimicrobial acid dye compound of the present invention has a blue color, and when mixed, expresses various colors, and dyes the fiber by using the same to show strong antimicrobial properties, inhibiting the growth and growth of microorganisms, preventing infectious diseases, preventing odor, Functional antibacterial fiber products can be produced that can prevent contamination and embrittlement.
은 함유, 항균 산성 염료, 설폰아미드, 항균 섬유, 실버설파다이아진, 항균성. Silver-containing, antibacterial acid dyes, sulfonamides, antibacterial fibers, silver sulfadiazine, antibacterial.
Description
본 발명은 강력한 항균성 반응기로서 설폰아미드(sulfonamides)계 항균제, 특히 은 함유 설파제를 염료의 중간체에 결합시켜 제조한 은 함유 항균 산성 염료 및 그의 제조방법, 그리고 상기 은 함유 항균 산성 염료로 염색되어 다양한 색상과 항균성을 동시에 지니는 항균 섬유에 관한 것이다.The present invention is a strong antimicrobial reactor, a sulfonamides-based antimicrobial agent, in particular a silver-containing antimicrobial acid dye prepared by binding a silver-containing sulfa agent to the intermediate of the dye, and a method for producing the same, and dyed with the silver-containing antimicrobial acid dyes in various colors An antimicrobial fiber having both antimicrobial and antimicrobial properties.
일반적으로 의류나 침구류 등에 사용되는 섬유 제품은 소비자의 다양한 취향에 따라 섬유 재료를 원하는 빛깔로 착색하는 염색공정을 거쳐야만 한다.In general, textile products used in clothing and bedding, etc. must go through a dyeing process for coloring the textile material in the desired color according to the consumer's various tastes.
그런데 이와 같이 제조된 각종 섬유류 제품은 보관불량에 의하여 미생물이 서식하거나, 인체와의 접촉으로 인체의 분비물을 영양원으로 하여 미생물이 서식 및 증식하여 인체의 건강을 위협하거나 제품에 악취가 발생하고 오염, 변색 취하 등이 발생하여 제품의 내구성, 견뢰도 등 품질을 저하시키는 주요 요인이 되기도 한다.However, various fiber products manufactured as described above are inhabited by microorganisms due to poor storage, or by contact with the human body as a nutrient source of the secretions of the human body, the microorganisms inhabit and multiply, threatening the health of the human body, or causing odors in the products, Discoloration and withdrawal may occur, which may be a major factor in degrading product quality, such as durability and color fastness.
이러한 이유로 섬유 제품은 병원균 침입의 매개체 또는 서식처가 되기도 하는데 만일 섬유제품에 항균성을 부여하게 되면, 미생물의 서식이나 증식을 억제하여 전염성질환 예방, 악취예방, 섬유의 오염과 취화를 방지할 수 있는 기능성 섬유 제품을 얻을 수 있을 것이다.For this reason, textile products may be a carrier or a habitat for pathogen invasion. If they give antimicrobial properties to textile products, they can prevent the growth and proliferation of microorganisms, preventing infectious diseases, preventing odors, and preventing fiber contamination and embrittlement. You will be able to get a textile product.
통상 항균 방취 가공법은 크게 후처리 가공법과 원사 개량법으로 나누어진다. 후처리 가공법에는 항균성을 지니는 삼백초와 같은 천연물질에서부터 염료성분을 추출하여 항균성을 부여하는 방법(대한민국 공개특허 제 2000-007593호)과 유기 금속화합물이나 유기물 등의 항균물질 성분을 섬유와 가교결합시켜 반응성 수지로 섬유표면에 열고정 시키는 방법, 그리고 항균물질을 섬유표면에 흡착 고정시키는 방법이 등이 있다. 그리고 원사 개량법에는 합성섬유의 제조 단계에서 무기계 항균제를 고분자 사이에 혼합 방사시켜 섬유 내부에 함유하는 방법과 재생섬유의 제조 단계에서 응고, 재생공정 중에 섬유내부에 동 화합물을 분산시키는 방법, 그리고 항균성을 가지는 유기계 공중합 성분을 만들어 고분자를 합성하는 방법 등이 있다.Usually, antibacterial and deodorant processing methods are largely divided into post-treatment processing methods and yarn improvement methods. In the post-treatment processing method, the dye component is extracted from natural substances such as tricotweed, which has antimicrobial properties, to give antimicrobial properties (Korean Patent Publication No. 2000-007593), and antimicrobial components such as organometallic compounds and organic substances are crosslinked with fibers. Heat-fixing method on the fiber surface with reactive resin, and adsorption-fixing method of antimicrobial material on the fiber surface. In the yarn improvement method, a method of mixing and spinning an inorganic antimicrobial agent between polymers in a manufacturing step of a synthetic fiber and interposing the inside of the fiber, and a method of dispersing the copper compound inside the fiber during the coagulation and regeneration process of a regenerated fiber, and antimicrobial activity There is a method of synthesizing a polymer by making an organic copolymer component having a.
한편, 항균방취가공은 살균이나 치료의 목적이 아니고, 섬유 상에 세균이나 곰팡이의 서식 및 증식을 억제하기 위한 가공으로서, 높은 항균력보다는 어느 수준 이상의 항균효과를 지속적으로 유지함과 동시에 인체에 절대적으로 안전하여야 한다. 이러한 의미로 볼 때 후처리 가공법에서 사용된 유기금속 화합물들인 유기 수은화합물, 유기 주석 화합물, 유기 구리화합물, 유기아연 화합물들은 살균성이 매우 우수하나, 이들 화합물은 독성과 같은 인체 안전성 등의 문제로 지금은 일본, 미국 등에서 사용규제를 받아 대부분 의류용 섬유가공에는 사용되지 않고, 카펫, 벽지 등 인체와 접촉하지 않는 분야나 산업용 등 일부에 사용되고 있다. 더욱이 이들 유기금속계 화합물들은 섬유와의 접착 및 세탁 내구성 등에 문제가 있어서 항구적 항균성을 갖는데는 한계가 있다. On the other hand, antibacterial and deodorant processing is not for the purpose of sterilization or treatment, but is a process for suppressing the growth and growth of bacteria and fungi on the fiber. shall. In this sense, organometallic compounds such as organometallic mercury compounds, organotin compounds, organocopper compounds, and organozinc compounds used in the post-treatment process have very good bactericidal properties. Is used in Japan, the United States, etc., most of which are not used in textile processing for garments, but are used in some areas such as carpets, wallpaper, etc. that do not come into contact with the human body. Moreover, these organometallic compounds have problems in adhesion to fibers and durability of laundry, and thus have a limit in enduring antimicrobial properties.
또한 일반 유기계 항균물질은 무기계에 비해 가공이 용이하며, 기계적 물성, 투명도, 색상 등에 큰 영향을 끼치지 않는다는 점에서 현재까지 많이 사용은 되고 있으나 앞에서 언급한 바와 같이 항균효과의 지속성이 결여되고 특히 내열성이 열등하다는 점에서 용도가 한정되어 있다. 또한 일부 유기계 항균물질은 피부 자극성, 최루성 등의 문제를 일으키는 것도 있다. 또한 천연물질로부터 추출한 염료의 경우 염색단계에서부터 항균성을 부여하는 장점은 있으나 계절적인 제한으로 염료의 추출이 제한적이고 천연염료의 단점인 견뢰도 증진을 위하여 또 다른 중금속을 이용한 매염염법을 이용해야 하는 단점이 있다.In addition, general organic antimicrobial materials are easier to process than inorganic ones, and have been widely used until now because they do not affect mechanical properties, transparency, color, etc., but as mentioned above, the antimicrobial effect is not sustained and in particular, heat resistance. Use is limited in that it is inferior. In addition, some organic antimicrobial substances cause problems such as skin irritation and tearing. In addition, dyes extracted from natural materials have the advantage of imparting antimicrobial properties from the dyeing stage, but due to seasonal limitations, the extraction of dyes is limited and the disadvantages of using the mordant salt method using another heavy metal to improve the fastness, which is a disadvantage of natural dyes. have.
무기계의 항균물질은 지올라이트, 실리카, 알루미나 등의 무기담체에 은, 구리, 아연 등과 같이 항균성이 뛰어난 금속이온을 치환시킨 것으로서, 미세한 세공을 가진 3차원의 골격구조를 지니기 때문에 표면적이 크고 내열성이 우수하다. 한편 은, 구리, 아연 등의 금속은 항균력이 강하고 안전성이 높은 몇 안되는 금속으로서 현재까지는 인체에 무해한 것으로 판명되어 있다. 무기계는 종래의 유기계 항균물질과 비교하여 내열성이 높고 휘발, 분해 등을 일으키지 않는 등 안정성이 높기 때문에 넓은 용도로 응용할 수 있으며, 무기계 항균물질의 항균효과는 활성산소 이온에 의해 발현되기 때문에 유기계 항균물질에서는 볼 수 없는 뛰어난 장점을 가 지고 있다. 그러나 은, 구리, 아연 등의 금속이온은 수지를 열화시키거나 황변현 상을 야기해 상품가치를 현저하게 저하시킬 우려가 있다. 또한 무기계 항균물질은 일반적으로 그 평균입경이 수 미크론 이상으로 크고 입도 분포의 폭도 넓기 때문에 미세한 섬유에 혼합방사 할 경우 사절의 원인이 될 수도 있다. Inorganic antimicrobial material is a substitute for inorganic ions such as zeolite, silica, alumina, etc. and metal ions with excellent antimicrobial properties such as silver, copper and zinc, and has a three-dimensional skeletal structure with fine pores. great. On the other hand, metals such as silver and copper and zinc are one of the few metals with strong antibacterial activity and high safety, and have been found to be harmless to the human body. Inorganic type has high heat resistance compared to conventional organic type antimicrobial material and has high stability such as not causing volatilization and decomposition. Therefore, it can be applied to a wide range of applications.The antimicrobial effect of inorganic type antimicrobial material is expressed by active oxygen ions. It has an outstanding advantage that you cannot see. However, metal ions such as silver, copper, zinc and the like may degrade the resin or cause yellowing, thereby significantly lowering the commodity value. In addition, the inorganic antimicrobial material is generally more than a few microns in average particle size and wide range of particle size distribution may be the cause of trimming when mixed with fine fibers.
본 발명은 상기와 같은 염료로서 이용되는 종래 항균물질의 문제점을 해결하기 위해 제안된 것으로써, 본 발명의 목적은 강력한 항균기를 포함하는 산성염료 및 그의 제조방법을 제공하는 것이다. 특히, 은(Ag+)이온에 의한 항균작용과 설파제자체의 항균작용이 함께 상승작용하여 더 강력한 항균작용을 할 것에 착안하여 은 이온(Ag+)을 함유한 실버설파다이아진을 이용한 본 발명을 완성하기에 이르렀다. The present invention has been proposed to solve the problems of the conventional antimicrobial material used as the dye as described above, an object of the present invention is to provide an acid dye containing a strong antimicrobial group and a method for producing the same. In particular, the present invention using silver sulfadiazine containing silver ions (Ag + ) is focused on the antimicrobial action of silver (Ag + ) ion and the antibacterial action of sulfa agent itself to make stronger antibacterial action. It was completed.
구체적으로, 본 발명은 섬유에 사용되는 산성염료 모체에 항균 작용성이 우수한 설폰아미드계 항균제 중 실버설파다이아진(Silver Sulfadiazine)을 도입시켜 항균 산성 염료를 제조하는 방법을 제공한다. Specifically, the present invention is a sulfonamide-based antimicrobial agent having excellent antibacterial activity on the acid dye matrix used in the fiber The present invention provides a method of preparing an antimicrobial acid dye by introducing silver sulfadiazine.
또한 본 섬유제품에 실시되는 항균 가공을 염색 공정에서부터 부여하며, 항균을 목적으로 하는 추가 공정이 필요하지 않고, 염료가 분해되어 직·편물의 색상이 소색되지 않고, 항균성이 오랫동안 지속되는 우수한 내구성의 항균 섬유를 제공하는 것을 다른 목적으로 한다.In addition, it gives the antibacterial processing to the textile products from the dyeing process, and does not require any additional process for the purpose of antibacterial, and the dye is decomposed, so that the color of the knitted fabric is not discolored, and the antibacterial property is long lasting. Another object is to provide antimicrobial fibers.
본 발명은 은(Ag)을 함유하는 설파제, 즉 은 함유 설폰아미드류를 디아조화체로하는 다음 화학식 1의 은 함유 항균 산성 염료 및 그의 제조방법에 관한 것이다.The present invention relates to a silver-containing antimicrobial acid dye represented by the following formula (1) containing a silver (Ag) -containing sulfa agent, that is, a silver-containing sulfonamide as a diazo compound, and a method for producing the same.
또한, 본 발명은 상기 은 함유 항균 산성 염료로 염색하여 다양한 색상과 항균성을 동시에 지니는 기능성 항균 섬유에 관한 것이다. The present invention also relates to a functional antimicrobial fiber having various colors and antimicrobial properties by dyeing with the silver-containing antimicrobial acid dye.
(상기식에서, R은 SO3H 또는 SO3Na 이다)(Wherein R is SO 3 H or SO 3 Na)
이하, 본 발명의 구성에 대해 더욱 상세히 설명한다. Hereinafter, the configuration of the present invention will be described in more detail.
일반적으로 사용되고 있는 항균성 물질로는 페니실린. 설폰아미드, 플루오로 퀴놀론, 테트라 사이클린, 아미노글루코사이드 등이 있다. 이들 중 범용적으로 많이 사용되며 염료의 중간체로서 사용이 가능한 것은 테트라 사이클린, 설폰아미드, 퀴놀론 등이 있다. Commonly used antimicrobial agents are penicillin. Sulfonamides, fluoroquinolones, tetracyclines, aminoglucosides and the like. Among these, it is widely used and can be used as an intermediate of dyes such as tetracycline, sulfonamide, and quinolone.
본 발명에서는 이들 물질 중 미생물내 효소의 핵산 합성 등 대사기능을 억제하여 항균성을 부여하는 설폰아미드계 항균제를 사용하였다. In the present invention, sulfonamide-based antimicrobial agents are used to inhibit the metabolic functions such as nucleic acid synthesis of enzymes in microorganisms and to provide antimicrobial activity.
설파제(sulfonamide drug), 즉 설폰아미드(sulfonamides)류 항균제는 SO2NH2기를 가지는 항균제의 일종으로서 미생물의 엽산 합성을 길항하는 설파닐아미드의 유도체들을 총칭하는 것으로서, 그램-양성 구균(연쇄구균(streptococci), 폐렴구균(pneumococci) 등), 그램-음성 구균 (수막알균(meningococci), 임균(gonococci) 등), 그램-양성균 (대장균(Escherichia coli), 이질균(shigellae) 등), 및 기타 다양한 세균 발육 억제하는 항균물질이다. 1932년 독일 과학자 도마흐크(Gerhard Domagk)에 의해 개발된 Prontosil rubrum이 체내에서(in-vivo) 설파닐아미드로 대사되어 강력한 항균효과가 발현됨이 최초로 밝혀진 이후 매우 많은 유도체가 합성되었다. 설폰아미드는 설파닐아미드 분자구조를 공통적으로 가지고 있다. 설폰아미드계 항균물질로는 다양한 종류가 있는데 설파피리딘(sulfapyridine), 설파다이아진(sulfadiazine), 실버설파다이아진(silversulfadiazine), 설파메라진(sulfamerazine), 설파메톡신(sulfamethoxine), 설파피라진(sulfapyrazine), 프탈일설파티아졸(phthalylsulfathiazole), 설파티아졸(sulfathiazole), 마페나이드(Mafenide), 설파디미딘(Sulfadimidine), 설파메타진(sulfamethazine), 설파메톡사졸(Sulfamethoxazole), 설파닐아미드(Sulfanilamide), 설파메톡시피리다진(sulfamethoxypyridazine), 설파구아니딘(sulfaguanidine), 설파다이메톡신(sulfadimethoxine), 설피속사졸(Sulfisoxazole), 설파독신(sulfadoxine), 설파메티졸(sulfamethizole), 설파살아진(sulphasalazine), 설핀피라존(sulphinpyrazone) 등이 있다.Sulfonamide drugs, or sulfonamides, are a type of antimicrobial agent with SO 2 NH 2 groups, which collectively refer to derivatives of sulfanilamide that antagonize the folate synthesis of microorganisms. streptococci, pneumococci, etc.), Gram-negative cocci (meningococci, gonococci, etc.), Gram-positive bacteria (Escherichia coli, shigellae, etc.), and various other bacteria It is an antibacterial substance that suppresses development. Prontosil rubrum, developed by German scientist Gerhard Domagk in 1932, was metabolized into in-vivo sulfanylamides, and a large number of derivatives have been synthesized since it was first shown to express potent antimicrobial effects. Sulfonamides have a sulfanylamide molecular structure in common. There are various types of sulfonamide-based antimicrobial agents such as sulfapyridine, sulfadiazine, silversulfadiazine, sulfamerazine, sulfamethoxine, and sulfapyrazine. ), Phthalylsulfathiazole, sulfathiazole, mafenide, sulfadimidine, sulfamethazine, sulfamethoxazole, sulfanilamide , Sulfamethoxypyridazine, sulfaguanidine, sulfadimethoxine, sulfisoxazole, sulfadoxine, sulfamethizole, sulfasalzine And sulfinpyrazone.
본 발명에서는 그 중에서 염료의 중간체로서 가장 합성이 용이하며, 항균효과가 우수하여 가장 많이 사용되는 설폰아미드계 항균제인 하기 일반식 1의 실버설파다이아진(모노실버-4-아미노-N-피리미딜벤젠설폰아미드)을 사용하여 염료를 합성한다. In the present invention, the silver sulfadiazine (monosilver-4-amino-N-pyrimidyl) of the general formula 1, which is the most easily used as an intermediate of the dye, and the sulfonamide-based antimicrobial agent, which is most commonly used as an intermediate of dyes. Benzenesulfonamide) to synthesize the dye.
(일반식 1) 실버설파다이아진(General Formula 1) Silver Sulfa Diazine
실버설파다이아진(silver sulfadiazine)은 설파다이아진의 유도체로서 다수의 그램-양성 및 그램-음성 미생물에 대한 항균능력 뿐만 아니라, 이스트에 대해서도 유효하고, 2도 및 3도 화상패혈증의 예방 및 치료를 위한 국소용 및 외용 항감염증제로 사용된다. Silver sulfadiazine is a derivative of sulfadiazine and is effective against yeast as well as antimicrobial ability against many gram-positive and gram-negative microorganisms, and is effective for the prevention and treatment of second and third degree burn sepsis. Used as a topical and external anti-infective.
본 발명에 의한 상기 화학식 1의 은 함유 항균 산성 염료의 제조방법을 설명한다. 구체적으로, 본 발명에서는 하기 일반식 1의 실버설파다이아진을 하기 일반식 2의 1,4-디브로모 안트라퀴논-2-설폰산과 축합 반응을 진행시켜 하기 화학식 1의 항균 산성 염료를 합성한다.Silver containing formula 1 according to the present invention The production method of the antimicrobial acid dye will be described. Specifically, in the present invention, the condensation reaction of silver sulfadiazine of the following general formula (1) with 1,4-dibromo anthraquinone-2-sulfonic acid of the following general formula (2) synthesizes an antimicrobial acid dye of the general formula (1) .
(일반식 1) 실버설파다이아진(General Formula 1) Silver Sulfa Diazine
(일반식 2) 1,4-디브로모 안트라퀴논-2-설폰산1,4-dibromo anthraquinone-2-sulfonic acid
(화학식 1)(Formula 1)
(상기식에서, R은 SO3H 또는 SO3Na 이다)(Wherein R is SO 3 H or SO 3 Na)
상술한 바와 같은 본 발명의 특징 및 기타 장점들은 후술되는 비한정적인 실시예의 기재로 부터 보다 명백하게 될 것이다. 그러나, 이하의 실시예는 단지 본 발명의 구체적 구현예로서 예시적인 것을 뿐이므로 본 발명의 범위를 국한시키는 것으로 이해되어서는 안 될 것이다.Features and other advantages of the present invention as described above will become more apparent from the description of the non-limiting examples described below. However, the following examples are merely illustrative as specific embodiments of the present invention and should not be understood as limiting the scope of the present invention.
실시예 1 : 화학식 2의 은 함유 항균 산성 염료의 제조Example 1 Preparation of Silver-Containing Antimicrobial Acid Dye of Formula 2
실버설파다이아진 0.02몰을 증류수에 분산시킨 후 염산(HCl) 6ml를 가하여 교반하며 녹인다. 별도의 반응용기에 1,4-디브로모 안트라퀴논-2-설폰산 0.02몰을 0.01몰의 탄산나트륨(Na2CO3)과 함께 증류수에 녹인다. 위 두용액을 천천히 섞은후 10% 탄산나트륨(Na2CO3)용액을 이용하여 pH를 9~10으로 유지한 후, 온도를 상승시켜 70~75℃ 유지하면서 2시간 동안 반응시킨다. 반응이 종결후 약 50℃까지 냉각시킨 후 pH를 7로 적정하고 염석과정을 거쳐 거름종이로 여과한 후 건조시키면, 상기 화학식 2와 같은 본 발명에 의한 청색의 은 함유 항균 산성 염료가 얻어진다.Dissolve 0.02 mol of silver sulfadiazine in distilled water, and add 6 ml of hydrochloric acid (HCl) to stir and dissolve. In a separate reaction vessel, 0.02 mol of 1,4-dibromo anthraquinone-2-sulfonic acid is dissolved in distilled water together with 0.01 mol of sodium carbonate (Na 2 CO 3 ). After slowly mixing the above two solutions using a 10% sodium carbonate (Na 2 CO 3 ) solution to maintain a pH of 9 ~ 10, the temperature is raised to 70 ~ 75 ℃ while maintaining the reaction for 2 hours. After completion of the reaction, the reaction solution was cooled to about 50 ° C., then titrated to 7, filtered through a filter paper through salting, and dried to obtain a blue silver-containing antimicrobial acid dye according to the present invention as shown in Formula 2.
이렇게 얻은 상기 화학식 2의 은 함유 항균 산성 염료 화합물의 1.0% 수용액에 빙초산과 분산제를 가하여 염액을 만든 후, 130℃에서 60분간 염색한후 소핑과 건조를 거쳐 염색된 항균 섬유를 제조하였다.The salt solution was prepared by adding glacial acetic acid and a dispersant to a 1.0% aqueous solution of the silver-containing antimicrobial acid dye compound of Formula 2 thus obtained, and then dyed at 130 ° C. for 60 minutes to prepare dyed antimicrobial fibers by soaping and drying.
< 항균성 평가 > <Antimicrobial Evaluation>
KS K 0693-2001, 직물의 항균성 시험방법을 이용하여 상기 합성된 청색 염료를 이용하여 각 1% o.w.f.의 농도로 염색된 나일론 평직 직물을 대상으로 항균성 시험을 행하여 본 발명에 의한 은 함유 항균 산성 염료의 항균성을 입증하는 다음 표 1과 같은 결과를 얻었다.KS K 0693-2001, Silver-containing antimicrobial acid dye according to the present invention by performing an antimicrobial test on a nylon plain weave fabric dyed at a concentration of 1% owf using the blue dye synthesized using the antimicrobial test method of the fabric To demonstrate the antimicrobial properties of the following Table 1 was obtained.
<항균성 시험 >Antimicrobial Test
본 발명의 은 함유 항균 섬유에 대한 항균성 시험 조건은 다음과 같다:The antimicrobial test conditions for the silver-containing antimicrobial fiber of the present invention are as follows:
1. 시험균종: 1) 균주 1: 황색포도알균(Staphylococcus aureus) ATCC 6538Test species: 1) Strain 1: Staphylococcus aureus ATCC 6538
2) 균주 2: 폐렴막대균(klebsiella pneumoniae) ATCC 4352 2) Strain 2: Klebsiella pneumoniae ATCC 4352
2. 접종균의 농도: 1) 균주 1: 1.3 X 105 개/ml 2. Concentration of inoculum: 1) Strain 1: 1.3 X 10 5 / ml
2) 균주 2: 1.5 X 105 개/ml 2) Strain 2: 1.5 X 10 5 pcs / ml
3. 증가율: 1) 균주 1: 34배 증식3. Growth rate: 1) Strain 1: 34-fold growth
2) 균주 2: 32배 증식 2) Strain 2: 32-fold multiplication
4. 대조편: 나일론(KS K 0905 -1996)4. Control: Nylon (KS K 0905 -1996)
5. 비이온 계면활성제: Tween80 (0.05%)5. Nonionic Surfactant: Tween80 (0.05%)
상술한 바와 같이 본 발명에 의한 은 함유 항균 산성 염료 화합물은 청색을 갖추고 있어 혼합시 다양한 색상을 발현하고, 이를 이용하여 섬유를 염색하면 강력한 항균성을 나타내어 미생물의 서식이나 증식을 억제하여 전염성질환 예방, 악취예방, 섬유의 오염과 취화를 방지할 수 있는 기능성 항균 섬유 제품을 제조할 수 있다.As described above, the silver-containing antimicrobial acid dye compound according to the present invention has a blue color, and when mixed, expresses various colors, and when dyeing fibers using the same, it exhibits strong antimicrobial properties and inhibits the growth or proliferation of microorganisms to prevent infectious diseases, Functional antibacterial fiber products which can prevent odors and prevent contamination and embrittlement of fibers can be prepared.
본 발명에 의하면 섬유 제품에 실시되는 항균 가공을 염색 공정에서부터 부여하며, 항균을 목적으로 하는 추가 공정이 필요하지 않고, 염료가 분해되어 직· 편물의 색상이 소색되지 않고, 항균성이 오랫동안 지속되는 우수한 내구성의 항균 섬유 제품을 제조할 수 있다. According to the present invention, the antimicrobial processing to be applied to the textile product is given from the dyeing process, and an additional process for the purpose of antibacterial is not necessary, and the color of the knitted fabric is not degraded due to the decomposition of the dye, and the antibacterial property is excellent for a long time. Durable antibacterial fiber products can be produced .
본 발명은 이상과 같이 기재된 구체예에 대하여만 상세히 설명되었지만, 본 발명의 사상과 범위 내에서 변경이나 변형 할 수 있음은 본 발명이 속하는 분야의 당업자에게는 명백한 것이며 이러한 변경이나 변형은 이하에 첨부된 특허 청구범위에 의하여 제한되어져야 한다.Although the present invention has been described in detail only with respect to the embodiments described above, it can be changed or modified within the spirit and scope of the present invention will be apparent to those skilled in the art to which the present invention pertains. It should be limited by the claims.
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| KR20020057322A (en) * | 2001-01-04 | 2002-07-11 | 김이진 | Antibacterial red dye |
| KR20040104856A (en) * | 2003-06-04 | 2004-12-13 | 범아무역상사 주식회사 | Antibacterial azo dye having sulfanilamides as diazo-component |
| US20050011012A1 (en) | 2003-03-19 | 2005-01-20 | Regents Of The University Of California | Multifunctional antimicrobial dyes |
| KR20060034335A (en) * | 2004-10-18 | 2006-04-24 | 주식회사 코오롱 | Antibacterial dispersed dyes having silver-containing modified sulfonamides and a method of preparing the same and antibacterial fiber thereby |
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| KR20020057322A (en) * | 2001-01-04 | 2002-07-11 | 김이진 | Antibacterial red dye |
| US20050011012A1 (en) | 2003-03-19 | 2005-01-20 | Regents Of The University Of California | Multifunctional antimicrobial dyes |
| KR20040104856A (en) * | 2003-06-04 | 2004-12-13 | 범아무역상사 주식회사 | Antibacterial azo dye having sulfanilamides as diazo-component |
| KR20060034335A (en) * | 2004-10-18 | 2006-04-24 | 주식회사 코오롱 | Antibacterial dispersed dyes having silver-containing modified sulfonamides and a method of preparing the same and antibacterial fiber thereby |
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