KR20070029955A - 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 PDFInfo
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- 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
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- 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
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- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- 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
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- 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
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- 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
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Abstract
Description
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 재생섬유와 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. There is an outstanding advantage that is not seen in the. 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 없고, 반응온도가 98℃ 수준이기 때문에 통상적으로 60℃에서 염색이 가능한 면(cotton) 섬유를 염색하는 경우에도 염색온도를 98℃까지 올려야 하기 때문에 에너지 낭비가 심한 등의 문제가 있었다.However, the above-mentioned 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, and the reaction temperature. Since it is 98 ° C level, when dyeing cotton fibers that can be dyed at 60 ° C normally, the dyeing temperature has to be raised to 98 ° C, such as high energy waste.
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, 반응온도도 60℃ 수준으로 낮아 면 또는 양모 등의 천연섬유나 레이온 섬유 염색시 불필요한 에너지 낭비를 방지할 수 있고, 양모에 처리시 색상변화(변색)가 없는, 반응성 항균제 및 그의 제조방법을 제공하기 위한 것이다.An object of the present invention is to give only antimicrobial and antifungal properties without dyeing the treated textile product to a specific color, and to lower the reaction temperature to 60 ℃ level to prevent unnecessary energy waste when dyeing natural or rayon fibers such as cotton or wool. It is possible to provide a reactive antimicrobial agent and a method for preparing the same, which are free from 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.
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. 한편, 다른 비이커에 하기 일반식 2의 시아누릭 클로라이드를 일반식 1의 설파다이아진과 같이 만든다. 일정시간이 지난 후 시아누릭 클로라이드 용액을 설파다이아진 용액에 천천히 가하여 축합반응을 진행시켜 화학식 1의 반응성 항균제를 합성할 수 있 다.First, the sulfadiazine of the following general formula (1) is dissolved in water and kept at 0-5 ° C. On the other hand, in another beaker, cyanuric chloride of the general formula (2) is made like the sulfadiazine of the general formula (1). After a certain time, the cyanuric chloride solution may be slowly added to the sulfadiazine solution to proceed the condensation reaction to synthesize a reactive antimicrobial agent of Chemical Formula 1.
(일반식 1) 설파다이아진(Formula 1) Sulfaazine
(일반식 2) 시아누릭 클로라이드(Formula 2) Cyanuric chloride
(화학식 1)(Formula 1)
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 1의 반응성 항균제의 제조 1: Preparation of Reactive Antibacterial Agent of Formula 1
상기 일반식 2의 시아누릭 클로라이드 0.01 mole을 소량의 산을 가하여 100ml의 증류수에 교반하면서 0~5℃로 유지시키면서 균일하게 분산시킨다. 그리고 상기 일반식 1의 설파다이아진 0.01mole을 증류수에 넣고 소량의 산을 가한 후 5℃이하로 유지하면서 용해시킨다. 용해된 설파다이아진 용액을 천천히 시아누릭 클로라이드액에 가하면서 2시간동안 축합반응을 진행시킨다. 반응이 완료된 후, 냉각시켜 중화하고 물을 제거한 후 진공에서 건조시키면 상기 화학식 1의 반응성 항균제가 얻어진다.0.01 mole of cyanuric chloride of the general formula 2 is added to a small amount of acid and uniformly dispersed while maintaining at 0-5 ° C. while stirring in 100 ml of distilled water. In addition, 0.01 mole of sulfadiazine of the general formula 1 was added to distilled water, and a small amount of acid was added thereto. The condensation reaction was allowed to proceed for 2 hours while slowly adding the dissolved sulfadiazine solution to the cyanuric chloride solution. After the reaction is completed, the mixture is cooled to neutralize, removes water, and dried in vacuo to obtain a reactive antibacterial agent of Chemical Formula 1.
이렇게 얻은 상기 화학식 1의 반응성 항균제 0.1%o.w.f 수용액을 만들고 여기에 빙초산을 가하여 염액을 만든 후, 40℃에서 30분간 처리 , 소핑과 건조를 거쳐 항균 섬유를 제조하였다. Thus prepared 0.1% o.w.f aqueous solution of the reactive antimicrobial agent of Formula 1 was added to glacial acetic acid to form a salt solution, and then treated at 40 ℃ 30 minutes, soaping and drying to prepare an antimicrobial fiber.
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
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.
또한, 본 발명을 섬유 연삭 공정에 사용시에는 본 발명의 반응온도가 천연섬유 및 레이온 섬유의 통상적인 염색온도보다 낮아 본 발명과 섬유간의 공유결합 반응을 위해 염색온도를 통상적인 염색온도 이상으로 올려줄 필요가 없다.In addition, when the present invention is used in the fiber grinding process, the reaction temperature of the present invention is lower than the normal dyeing temperature of the natural fiber and rayon fiber, so that the dyeing temperature can be raised above the conventional dyeing temperature for the covalent bond reaction between the present invention and the fiber. no need.
그로인해 염색공정이 간단해지고 에너지 낭비도 방지할 수 있다.This simplifies the dyeing process and prevents energy waste.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008096918A1 (en) * | 2007-02-09 | 2008-08-14 | Kolon Industries, Inc | Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby |
| KR20200090481A (en) | 2019-01-21 | 2020-07-29 | (주)휴앤스킨 | Composition of antibacterial agent containing industrial preservatives |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008096918A1 (en) * | 2007-02-09 | 2008-08-14 | Kolon Industries, Inc | Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby |
| KR20200090481A (en) | 2019-01-21 | 2020-07-29 | (주)휴앤스킨 | Composition of antibacterial agent containing industrial preservatives |
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