KR20070029956A - Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby - Google Patents

Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby Download PDF

Info

Publication number
KR20070029956A
KR20070029956A KR1020050084630A KR20050084630A KR20070029956A KR 20070029956 A KR20070029956 A KR 20070029956A KR 1020050084630 A KR1020050084630 A KR 1020050084630A KR 20050084630 A KR20050084630 A KR 20050084630A KR 20070029956 A KR20070029956 A KR 20070029956A
Authority
KR
South Korea
Prior art keywords
reactive
fibers
formula
antimicrobial
represented
Prior art date
Application number
KR1020050084630A
Other languages
Korean (ko)
Inventor
성 희 박
Original Assignee
주식회사 코오롱
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 코오롱 filed Critical 주식회사 코오롱
Priority to KR1020050084630A priority Critical patent/KR20070029956A/en
Publication of KR20070029956A publication Critical patent/KR20070029956A/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • D06M13/268—Sulfones
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • D06M13/332—Di- or polyamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Reactive antibiotics, a method for preparing the same antibiotics and antibacterial fibers treated thereby are provided to confer improved antibacterial effects on the fibers without color change in the fibers by using compound having reaction group capable of forming a covalent bond with natural and rayon fibers. The reactive antibiotic represented by the chemical formula(1) is provided, wherein X is Br or Cl. The reactive antibiotic represented by the chemical formula(1) is prepared by condensing sulfadiazine represented by the general formula(1) with alpha,beta-dibromopropionyl chloride represented by the general formula(2) or alpha,beta-dichloropropionyl chloride represented by the general formula(3). The antibacterial fibers are prepared by treating fibers with the reactive antibiotics represented by the chemical formula(1).

Description

반응성 항균제, 그의 제조방법 및 이로 처리된 항균 섬유{Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby.}Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby.

본 발명은 강력한 항균성을 갖는 설파다이아진(4-아미노-N-2-피리미디닐벤젠설폰아미드)[이하 "설파다이아진"이라 한다]에 면, 레이온, 양모, 폴리비닐알콜 섬유, 라이오셀(Lyocell)등과 같은 천연섬유 및 재생 섬유와 공유결합이 가능한 반응성기가 결합된 반응성 항균제, 그의 제조방법 및 이로 처리된 항균 섬유에 관한 것이다.The present invention relates to sulfadiazine (4-amino-N-2-pyrimidinylbenzenesulfonamide) having strong antimicrobial properties (hereinafter referred to as "sulfadiazine"), cotton, rayon, wool, polyvinyl alcohol fibers, and lyocells. The present invention relates to a reactive antimicrobial agent having a reactive group capable of covalent bonding with natural fibers and recycled fibers such as (Lyocell), a method for preparing the same, and antibacterial fibers treated therewith.

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 미분산시키는 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 synthetic fiber and containing the inside of the fiber, and a method of undispersing the copper compound in the fiber during coagulation and regeneration of the regenerated fiber, and There is a method of synthesizing a polymer by making an organic copolymer component having antibacterial properties.

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 구리, 아연 등과 같이 항균성이 뛰어난 금속이온을 치환시킨 것으로서, 미세한 세공을 가진 3차원의 골격구조를 지니기 때문에 표면적이 크고 내열성이 우수하다. 한편 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 가지고 있 다. 그러나 구리, 아연 등의 금속이온은 수지를 열화시키거나 황변현상을 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 substituted with inorganic ion such as zeolite, silica, alumina and other metal ions with excellent antimicrobial properties such as copper and zinc, and has a three-dimensional skeletal structure with fine pores. . On the other hand, metals such as copper and zinc are one of the few metals with strong antibacterial activity and high safety, and have been proved to be harmless to 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 is not seen in However, metal ions such as copper and zinc may deteriorate 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.

한편, 대한민국 공개특허 제2002-57322호에서는 반응성 아조염료 분자내에 항균물질인 실버설파다이아진기를 도입시켜 강력한 항균력을 갖는 반응성 아조염료를 게재하고 있다.On the other hand, Korean Patent Laid-Open Publication No. 2002-57322 discloses a reactive azo dye having a strong antibacterial power by introducing a silver sulfadiazine group, which is an antimicrobial substance, in a reactive azo dye molecule.

그러나, 상기의 종래 반응성 아조염료는 반응성 아조염료 분자와 실버설파다이아진을 반응시킬때 반응수율이 낮고, 염료이기 때문에 염색이 불필요한 원단에 항균성만 부여하는 용도로는 사용이 될 수 없는 등의 문제가 있었다.However, the conventional reactive azo dyes have a low reaction yield when reacting the reactive azo dye molecules with silver sulfadiazine, and because they are dyes, they cannot be used for the purpose of providing only antimicrobial properties to fabrics that do not need dyeing. There was.

또한, 상기의 종래 반응성 아조염료는 양모섬유에 적용시 양모와 은(Ag)이 결합하여 은(Ag)의 항균성이 거의 발현되지 못하는 문제점이 있었다.In addition, the conventional reactive azo dye has a problem in that the antimicrobial activity of silver (Ag) is hardly expressed by the combination of wool and silver (Ag) when applied to wool fibers.

본 발명의 목적은 처리 섬유제품을 특정 색상으로 염색하지 않으면서 항균성과 항진성만 부여하고, 양모에 처리시 색상변화(변색)가 없는, 반응성 항균제 및 그의 제조방법을 제공하기 위한 것이다.It is an object of the present invention to provide a reactive antimicrobial agent and a method for producing the same, which gives only antimicrobial and antifungal properties without dying the treated textile product to a specific color, and is free of color change (discoloration) upon treatment with wool.

이하, 본 발명을 상세하게 설명한다.EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated in detail.

먼저, 본 발명의 반응성 항균제는 강력한 항균성과 항진성을 갖는 설파다이아진에 첨연섬유 및 레이온 섬유와 공유결합이 가능한 반응성기가 결합되어 하기 화학식 1의 구조를 갖는다.First, the reactive antimicrobial agent of the present invention has a structure of Formula 1 by combining a reactive group capable of covalently bonding with the leading fibers and rayon fibers to sulfadiazine having strong antimicrobial properties and antifungal properties.

(화학식 1)(Formula 1)

Figure 112005050801339-PAT00002
Figure 112005050801339-PAT00002

(상기식에서, X는 Br 혹은 Cl 이다)  Wherein X is Br or Cl

설파디아진은 헤모필루스 인풀루엔자(Haemophilus influenzae)에 의해 발병한 수막염(meningitis), 무른궤양(chancroid), 급성 요로감염증, 클로로퀸 저항성 말라리아 원충(chloroquine-resistant plasmodia)에 의해 발병한 성병림프육아종(lymphogranuloma venereum) 및 열대열말라리아(falciparum malaria)의 조기 징후등의 감염증 치료 및 예방에 유효한 설파제이다. Sulfadiazine is a lymphogranuloma caused by meningitis, chancroid, acute urinary tract infection, and chloroquine-resistant plasmodia caused by Haemophilus influenzae. It is an effective sulfa agent for the treatment and prevention of infectious diseases such as venereum) and early signs of falciparum malaria.

본 발명에 따른 상기 화학식 1의 반응성 항균제의 제조방법을 설명한다. It describes a method for producing a reactive antimicrobial agent of Chemical Formula 1 according to the present invention.

먼저, 하기 일반식 1의 설파다이아진을 물에 녹여 0~5℃로 유지한다. 다음으로, 뷰렛에 있는 하기 일반식 2의 α,β-디브로모프로피오닐 클로라이드(α,β-dibromopropionyl chloride) 또는 하기 일반식 3의 α,β-디클로로프로피오닐 클로라이드(α,β-dichloropropionyl chloride)를 일반식 1의 설파다이아진의 수용액에 천천히 떨어뜨린다. 일정시간이 지난 후 KOH 10% 용액을 반응액에 가하여 탈할로겐화 반응을 진행함으로써 하기 화학식 2 또는 화학식 3의 반응성 항균제를 합성할 수 있다. First, the sulfadiazine of the following general formula (1) is dissolved in water and kept at 0-5 ° C. Next, α, β-dibromopropionyl chloride (α, β-dibromopropionyl chloride) of the following general formula (2) or α, β-dichloropropionyl chloride of the following general formula (3) in the burette ) Is slowly dropped into an aqueous solution of sulfadiazine of the general formula (1). After a certain time, a reactive antibacterial agent of the following Chemical Formula 2 or 3 may be synthesized by adding a 10% KOH solution to the reaction solution to proceed with a dehalogenation reaction.

(일반식 1) 설파다이아진(Formula 1) Sulfaazine

Figure 112005050801339-PAT00003
Figure 112005050801339-PAT00003

(일반식 2) α,β-디브로모프로피오닐 클로라이드(α,β-dibromopropionyl chloride)(Formula 2) α, β-dibromopropionyl chloride

Figure 112005050801339-PAT00004
Figure 112005050801339-PAT00004

(일반식 3) α,β-디클로로프로피오닐 클로라이드(α,β-dichloropropionyl chloride)(Formula 3) α, β-dichloropropionyl chloride

Figure 112005050801339-PAT00005
Figure 112005050801339-PAT00005

Figure 112005050801339-PAT00006
Figure 112005050801339-PAT00006

Figure 112005050801339-PAT00007
Figure 112005050801339-PAT00007

이하, 실시예를 통하여 본 발명을 더욱 구체적으로 살펴본다.Hereinafter, the present invention will be described in more detail with reference to Examples.

그러나, 하기 실시예는 단지 본 발명의 구체적인 구현예로서 본발명의 권리범위를 한정하는 것은 아니다.However, the following examples are not intended to limit the scope of the invention as merely specific embodiments of the present invention.

실시예Example 1: 화학식 2의 반응성 항균제의 제조 1: Preparation of Reactive Antibacterial Agent of Formula 2

상기 일반식 1의 설파다이아진 0.01mole을 증류수에 넣고 소량의 산을 가한 후 5℃이하로 유지하면서 용해시킨다. 별도 준비된 뷰렛에 상기 일반식 2의 α,β-디브로모프로피오닐 클로라이드 (α,β-dibromopropionyl chloride) 0.01mole을 넣은 후 상기 설파다이아진 용액에 천천히 가하면서 2시간동안 축합반응을 진행시킨다. 1차 반응이 완료된 후 반응액의 온도를 20℃로 유지하며 KOH 10% 용액을 반응에서 첨가하면서 pH를 12로 유지하면서 탈브롬화반응을 진해시킨다. 탈브롬화반응 완료 후 반응액을 중화하고 물을 제거한 후 진공에서 건조시키면 상기 화학식 2의 반응성 항균제가 얻어진다. 0.01 mole of sulfadiazine of the general formula 1 was added to distilled water, and a small amount of acid was added thereto. Into a separately prepared burette is added 0.01mole of α, β-dibromopropionyl chloride of the general formula (2), and then slowly added to the sulfadiazine solution, the condensation reaction proceeds for 2 hours. After completion of the first reaction, the temperature of the reaction solution is maintained at 20 ° C., while adding a KOH 10% solution in the reaction to maintain the pH at 12 while increasing the debromination reaction. After completion of the debromination reaction, the reaction solution is neutralized, water is removed, and dried in vacuo to obtain a reactive antibacterial agent of Chemical Formula 2.

Figure 112005050801339-PAT00008
Figure 112005050801339-PAT00008

실시예Example 2: 화학식 3의 반응성 항균제의 제조 2: Preparation of Reactive Antibacterial Agent of Formula 3

상기 일반식 1의 설파다이아진 0.01mole을 증류수에 넣고 소량의 산을 가한 후 5℃이하로 유지하면서 용해시킨다. 별도 준비된 뷰렛에 상기 일반식 3의 α,βcccccc디클로로프로피오닐 클로라이드(α,β-dichloropropionyl chloride) 0.01mole을 넣은 후 설파다이아진 용액에 천천히 가하면서 2시간동안 축합반응을 진행시킨다. 1차 반응이 완료된 후 반응액의 온도를 20℃로 유지하며 KOH 10% 용액을 반응에서 첨가하면서 pH를 12로 유지하면서 탈염소화반응을 진해시킨다. 탈염소화반응 완료 후 반응액을 중화하고 물을 제거한 후 진공에서 건조시키면 상기 화학식 3의 반응성 항균제가 얻어진다. 0.01 mole of sulfadiazine of the general formula 1 was added to distilled water, and a small amount of acid was added thereto. Into a separately prepared burette is added 0.01mole of α, βccccccdichloropropionyl chloride of the general formula (3), and then slowly added to the sulfadiazine solution to proceed the condensation reaction for 2 hours. After completion of the first reaction, the temperature of the reaction solution is maintained at 20 ° C. and the KOH 10% solution is added to the reaction while maintaining the pH at 12 while increasing the dechlorination reaction. After completion of the dechlorination reaction, the reaction solution is neutralized, water is removed, and dried in vacuo to obtain a reactive antimicrobial agent of Chemical Formula 3.

Figure 112005050801339-PAT00009
Figure 112005050801339-PAT00009

이렇게 얻은 상기 화학식 2와 화학식 3의 반응성 항균제 0.1%o.w.f 수용액을 만들고 여기에 빙초산을 가하여 염액을 만든 후, 98℃에서 30분간 처리 , 소핑과 건조를 거쳐 항균 섬유를 제조하였다.Thus prepared aqueous 0.1% o.w.f of the reactive antimicrobial agents of Formula 2 and Formula 3, and added to glacial acetic acid to form a salt solution, the antimicrobial fiber was prepared by treatment, soaping and drying at 98 ℃ 30 minutes.

상기와 같이 처리된 항균 섬유를 아래와 같은 방법으로 항균성을 시험한 결과는 표 1과 같다. The results of testing the antimicrobial properties of the antimicrobial fiber treated as described above are as follows.

<항균성 시험>Antimicrobial Test

본 발명의 항균 섬유에 대한 항균성 시험 조건은 다음과 같다:The antimicrobial test conditions for the antimicrobial fiber of the present invention are as follows:

1. 시험 방법: KSK 0693-20011.Test Method: KSK 0693-2001

2. 시험 균종: 1) 균주 1: 황색포도알균(Staphylococcus aureus) ATCC 65382. Test strains: 1) Strain 1: Staphylococcus aureus ATCC 6538

2) 균주 2: 폐렴막대균(klebsiella pneumoniae) ATCC 4352              2) Strain 2: Klebsiella pneumoniae ATCC 4352

3. 접종균의 농도: 1) 균주 Ⅰ - 1.3×105 개/ml 3. Inoculation concentration: 1) Strain I-1.3 × 10 5 / ml

2) 균주 Ⅱ - 1.5×105 개/ml2) Strain Ⅱ-1.5 × 10 5 pcs / ml

항균처리된 섬유의 항균성 시험 결과Antimicrobial Test Results of Antimicrobial Fibers 구분division 정균 감소율(%)Bacteriostatic reduction (%) 군주 ⅠLord Ⅰ 군주 ⅡLord Ⅱ 실시예 1(화학식 2)Example 1 (Formula 2) 99.999.9 99.999.9 실시예 2(화학식 2)Example 2 (Formula 2) 99.999.9 99.999.9

본 발명은 천연섬유 및 레이온 섬유와 공유결합을 형성하여 섬유의 색상에 영향을 주지 않으면서도 섬유에 항균성과 항진성을 부여할 수 있다.The present invention forms covalent bonds with natural fibers and rayon fibers to impart antimicrobial and antifungal properties to the fibers without affecting the color of the fibers.

특히, 본 발명은 양모섬유에 항균성을 부여할 때 양모섬유의 색상이 반색되는 것을 효과적으로 방지할 수 있다.In particular, the present invention can effectively prevent the color of the wool fibers are semi-colored when giving the antimicrobial properties to the wool fibers.

Claims (3)

하기 화학식 1의 반응성 항균제.Reactive antimicrobial agent of formula (1). (화학식 1)(Formula 1)
Figure 112005050801339-PAT00010
Figure 112005050801339-PAT00010
 (상기식에서, X는 Br 혹은 Cl 이다)   Wherein X is Br or Cl 하기 일반식 1의 설파다이아진과 하기 일반식 2의 α,β-디브로모프로피오닐 클로라이드(α,β-dibromopropionyl chloride) 또는 하기 일반식 3의 α,β-디클로로프로피오닐 클로라이드(α,β-dichloroprorionyl chloride)를 축합반응 시키는 것을 특징으로 하는 하기 화학식 1의 반응성 항균제 제조방법.Sulfadiazine of the following general formula (1) and α, β-dibromopropionyl chloride of the following general formula (2) or α, β-dichloropropionyl chloride of the following general formula (3) Dichloroprorionyl chloride) method of producing a reactive antimicrobial agent of the formula (1) characterized in that the condensation reaction. (일반식 1) 설파다이아진(Formula 1) Sulfaazine
Figure 112005050801339-PAT00011
Figure 112005050801339-PAT00011
 (일반식 2) α,β-디브로모프로피오닐 클로라이드(Formula 2) α, β-dibromopropionyl chloride
Figure 112005050801339-PAT00012
Figure 112005050801339-PAT00012
 (일반식 3) α,β-디클로로프로피오닐 클로라이드(Formula 3) α, β-dichloropropionyl chloride
Figure 112005050801339-PAT00013
Figure 112005050801339-PAT00013
 (화학식 1)(Formula 1)
Figure 112005050801339-PAT00014
Figure 112005050801339-PAT00014
 (상기식에서, X는 Br 혹은 Cl 이다)Wherein X is Br or Cl 제 1항의 반응성 항균제로 가공처리된 항균섬유.The antimicrobial fiber processed by the reactive antimicrobial agent of claim 1.
KR1020050084630A 2005-09-12 2005-09-12 Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby KR20070029956A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020050084630A KR20070029956A (en) 2005-09-12 2005-09-12 Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020050084630A KR20070029956A (en) 2005-09-12 2005-09-12 Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby

Publications (1)

Publication Number Publication Date
KR20070029956A true KR20070029956A (en) 2007-03-15

Family

ID=38101876

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020050084630A KR20070029956A (en) 2005-09-12 2005-09-12 Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby

Country Status (1)

Country Link
KR (1) KR20070029956A (en)

Similar Documents

Publication Publication Date Title
US6979491B2 (en) Antimicrobial yarn having nanosilver particles and methods for manufacturing the same
US20100003296A1 (en) Manufacturing methods and applications of antimicrobial plant fibers having silver particles
KR20190065981A (en) Anti-bacterial fabric product comprising anti-bacterial composition with effect of viability of lactic acid bacteria and anti-bacterial activity and manufacturing method thereof
CN109208174B (en) A kind of melt spraying non-woven fabrics and preparation method thereof
KR20070029955A (en) Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby
KR20070029956A (en) Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby
WO2008096918A1 (en) Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby
KR100821899B1 (en) A diazo type dyes and a method of manufacturing the same and fiber dyed thereby
KR20070023911A (en) Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby
KR100839511B1 (en) Antibacterail acidic dyes having the silver-sulfanilamides as diazo component and a method of preparing the same and antibacterial fiber thereby
JPH06313266A (en) Antibacterial fiber and its production
KR100839514B1 (en) Antibacterial dyes and a method of preparing the same and antibacterial fiber thereby
KR20070023910A (en) Reactive antibiotics and antibacterial fiber treated thereby
KR100821895B1 (en) Antibacterail acid dyes containing silver and a method of preparing the same and antibacterial fiber thereby
CN102619085B (en) Deodorization polyamide fiber and preparation method thereof
KR100839512B1 (en) Antibacterial acidic dyes having the sulphonamides as diazo component and antibacterial fiber thereby
KR100821898B1 (en) Antibacterail acid dyes containing silver and a method of preparing the same and antibacterial fiber thereby
KR20060034334A (en) Antibacterial dispersed dyes having silver-containing modified sulfonamides and a method of preparing the same and antibacterial fiber thereby
KR100821894B1 (en) Antibacterial dyes and antibacterial fiber thereby
KR100942197B1 (en) Antibacterail acid dyes containing silver and a method of preparing the same and antibacterial fiber thereby
KR20070023909A (en) Dyes and a method of manufacturing the same and fiber dyed thereby
KR20060034335A (en) Antibacterial dispersed dyes having silver-containing modified sulfonamides and a method of preparing the same and antibacterial fiber thereby
KR100581192B1 (en) Textile treatment agent of liquid type which have anti-bacterial, emit far-infrared ray and then absorb odor
KR100821897B1 (en) Antibacterail acid dyes containing silver and a method of preparing the same and antibacterial fiber thereby
Pachiyappan et al. Comparative study of antimicrobial activity of quaternary ammonium component coated knitted fabrics

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E601 Decision to refuse application