WO2008096918A1 - 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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- WO2008096918A1 WO2008096918A1 PCT/KR2007/000705 KR2007000705W WO2008096918A1 WO 2008096918 A1 WO2008096918 A1 WO 2008096918A1 KR 2007000705 W KR2007000705 W KR 2007000705W WO 2008096918 A1 WO2008096918 A1 WO 2008096918A1
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- Prior art keywords
- fibers
- reactive
- bacterial
- antibiotic
- preparing
- Prior art date
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- 239000000835 fiber Substances 0.000 title claims abstract description 53
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 32
- 230000003115 biocidal effect Effects 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 12
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000004744 fabric Substances 0.000 abstract description 11
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical group C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 abstract description 11
- 229920000297 Rayon Polymers 0.000 abstract description 9
- 239000003242 anti bacterial agent Substances 0.000 abstract description 9
- 239000002964 rayon Substances 0.000 abstract description 9
- 229960004306 sulfadiazine Drugs 0.000 abstract description 9
- 229940088710 antibiotic agent Drugs 0.000 abstract description 7
- 244000005700 microbiome Species 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 208000035473 Communicable disease Diseases 0.000 abstract description 3
- 230000002411 adverse Effects 0.000 abstract description 3
- 208000015181 infectious disease Diseases 0.000 abstract description 2
- 238000010186 staining Methods 0.000 abstract description 2
- 238000004043 dyeing Methods 0.000 description 16
- 239000000463 material Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000987 azo dye Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 150000002902 organometallic compounds Chemical class 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- -1 wool Polymers 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000002476 Falciparum Malaria Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 229920000433 Lyocell Polymers 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 229930182559 Natural dye Natural products 0.000 description 1
- 206010035500 Plasmodium falciparum infection Diseases 0.000 description 1
- 201000011336 Plasmodium falciparum malaria Diseases 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000534017 Saururus chinensis Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 210000003103 bodily secretion Anatomy 0.000 description 1
- 201000004308 chancroid Diseases 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940100892 mercury compound Drugs 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960003600 silver sulfadiazine Drugs 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table
- D06M11/42—Oxides or hydroxides of copper, silver or gold
-
- 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
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
-
- 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
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
Definitions
- the present invention relates to reactive antibiotics comprising reactive groups bonded to sulfadiazine (that is, 4-amino-N-2- pyrimidinylbezene sulfonamide) having strong anti-bacterial properties, the reactive groups of which are covalently bondable to natural fibers and regenerated fibers such as cotton, rayon, wool, polyvinylalcohol fiber, Lyocell, etc., a process of preparing the same and antibacterial fibers treated with the same.
- sulfadiazine that is, 4-amino-N-2- pyrimidinylbezene sulfonamide
- a fabric product used in garment or bedclothes needs to undergo a fiber material dyeing process with desired colors to satisfy different tastes of consumers.
- Such manufactured fabric product often becomes habitable for microorganisms due to poor care, allowing the microorganisms to inhabit and grow with normal bodily secretions as nutrient when the microorganisms contact directly with a human body so that it threatens health of the human body and/ or results bad odor, contamination, discoloration, brittleness of fiber, etc., thereby being a major cause to deteriorate quality of the fabric product such as durability, color fastness or the like.
- the fabric product may become a medium or habitat for pathogenic bacteria to invade the human body.
- the fabric product has anti-bacterial properties, it will become a functional fabric product that inhibits inhabitation or growth of microorganisms and, as a result, protects against infectious disease and bad odor, and prevents staining and brittleness of fiber of the fabric product.
- the post-treatment processes include: as disclosed in Korean Patent Laid-Open No. 2000-007593, a method for giving anti-bacterial properties to fibers, which includes extraction of dyeing ingredient from a natural material such as Saururus chinensis (Lour.) Baill with anti-bacterial properties; a method which cross-links an anti-bacterial material such as organometallic compound or organic material with fibers and thermally fixes the bonded product to surface of the fibers by using a reactant resin; a method which fixes an antibacterial material to surface of fibers by adsorption and so on.
- the fiber improving processes include: a method which comprises introducing an inorganic anti-bacterial agent within fibers by blend- spinning the inorganic anti-bacterial agent into polymer in a process of manufacturing synthetic fibers; a method which disperses a copper compound into fibers during coagulating and regenerating in a process of manufacturing regenerated fibers; a method for synthesizing polymer, which comprises organic copolymer ingredients with anti- bacterial properties and so on.
- the anti-bacterial and deodorization processes have not a purpose of sterilization or treatment of diseases but are to inhibit inhabitation and growth of microbes and/or fungi on fibers.
- the processes require that an anti-bacterial effect is continuously maintained at least a predetermined level rather than only exhibiting high anti-bacterial properties for a short time and must safe to human bodies.
- organic mercury compound, organic tin compound, organic copper compound and organic zinc compound among the organometallic compounds used in the post- treatment processes have very superior anti-bacterial properties, they also have a problem of safety to a human body such as toxicity.
- most of the organometallic compounds for garments are prohibited by countries such as Japan, U.S.A., etc. but are partially used in applications that do not involve direct contact with the human body, for example, production of carpet or wallpaper, or other industrial fields.
- organometallic compounds that have demonstrated problems of undesired adhesion to fibers and low laundry durability are restricted in their permanent anti-bacterial effect.
- general organic anti-bacterial materials that could be easily processed compared with inorganic materials and do not affect mechanical properties, transparency, color, etc., as much are widely used at present.
- use of the organic anti-bacterial materials is limited because their anti-bacterial effect is not continued for a long term as described above and they have inferior heat-resistance.
- some of the organic anti-bacterial materials often have disadvantages of causing skin irritation, tearing property and so on.
- Dyes extracted from natural materials have a merit that anti-bacterial properties are early given to fibers in a dyeing process. But, they have a restriction in extracting the dyes due to seasonal limitation and a disadvantage that mordant dyeing accompanied with additional heavy metals is required to improve color fastness as a defect of natural dyes.
- Inorganic anti-bacterial materials are obtained by substitution of an inorganic carrier such as zeolite, silica, alumina, etc. with metal ions such as copper, zinc, etc. having excellent anti-bacterial properties.
- the inorganic anti-bacterial materials that have three-dimensional structure formed with micro-fine pores demonstrate a large surface area and excellent heat- resistance. It is believed as of now that copper and zinc belong to a few metals with superior anti-bacterial effect and safety, and are harmless to the human body.
- the inorganic anti-bacterial materials have higher heat-resistance and stability sufficient not to cause volatilization and decomposition thereof in comparison to conventional organic anti-bacterial materials, thereby being used in a wide variety of applications.
- the inorganic anti-bacterial materials since they express anti-bacterial effect via activated oxygen ions, the inorganic anti-bacterial materials have an excellent anti-bacterial effect superior to the organic anti-bacterial materials.
- metal ions for example, copper or zinc that are apt to deteriorate resin or cause yellowing have a possibility of significantly lowering value of goods containing the same.
- the inorganic anti-bacterial materials may cause cutting of thread if the inorganic anti-bacterial materials are added to micro-fine fibers during blend-spinning, since they generally have a larger average particle diameter above micron units and a wider distribution of particle size.
- Korean Patent Laid-Open No. 2002-57322 discloses a reactive azo dye with strong anti-bacterial ability prepared by introducing silver sulfadiazine group, which is anti-bacterial component, into reactive azo dye molecules.
- An object of the present invention is to provide reactive antibiotics that give anti-bacterial and anti-fungal properties to a fabric product while not dyeing the product with specific color, have lowered reaction temperature of about 60 0 C and prevent undesirable waste of energy when the dyes are used to dye natural fibers such as cotton or wool, or rayon fiber, and a process of preparing the same.
- a reactive antibiotic of the present invention has a structure of reactive groups represented by the following chemical formula 1 bonded to sulfadiazine having strong anti-bacterial and anti-fungal properties, the reactive groups of which are covalently bondable to natural fibers and rayon fibers.
- A is H or Ag.
- Sulfadiazine is sulfa drug effective for treating and protecting infectious diseases including, for example, meningitis caused by
- sulfadiazine represented by general formula 1 is dissolved in water and maintained at 0 to 5°C.
- cyanuric chloride represented by general formula 2 is treated as same to sulfadiazine represented by the general formula 1. After a constant time, the cyanuric chloride solution is slowly added to the sulfadiazine solution to proceed condensation and synthesize the reactive antibiotics represented by the chemical formula 1
- A is H or Ag.
- A is H or Ag.
- the inventive antibiotic can form covalent bond with natural fibers and rayon fibers to give anti-bacterial and anti-fungal properties to the fibers without adverse effect to color of the fibers.
- the present reactive antibiotic is employed in a fiber dyeing process, it does not require increase of dyeing temperature above normal dyeing temperature in order to proceed covalent bonding process between the antibiotic and fibers, since the reactive antibiotic has reaction temperature lower than typical dyeing temperature of natural fibers and rayon fibers. Consequently, it results in a simple dyeing process and prevents waste of energy or saves energy consumption.
- 0.01 moles of cyanuric chloride represented by the general formula 2 is mixed with small amount of acid, fed into 100ml of distilled water under agitation, and uniformly dispersed in the distilled water while maintaining the dispersion at 3°C.
- 0.01 moles of sulfadiazine represented by the general formula 1 is fed into distilled water, mixed with small amount of acid and dissolved in the distilled water while maintaining the solution at 3°C.
- the sulfadiazine solution is slowly added to the cyanuric chloride solution to proceed condensation for 2 hours. After completing the reaction, the obtained solution is subjected to cooling, neutralization and water removal, and dried under vacuum conditions to produce the reactive antibiotic represented by the chemical formula 1 :
- 0.1% o.w.f. solution is produced by using the prepared reactive antibiotic represented by the chemical formula 1 in water and glacial acetic acid is added thereto to obtain a dye solution anti-bacterially treated.
- cotton fiber is introduced and treated at
- Strain I Straphylococcus aureus ATCC 6538
- the present inventive antibiotic can form covalent bond with natural fibers and rayon fibers to give antibacterial and anti-fungal properties to the fibers without adverse effect to color of the fibers.
- the present reactive antibiotic is employed in a fiber grinding process, it does not require increase of dyeing temperature above normal dyeing temperature in order to proceed covalent bonding process between the antibiotic and fibers, since the reactive antibiotic has reaction temperature lower than typical dyeing temperature of natural fibers and rayon fibers. Consequently, it results in a simple dyeing process and prevents waste of energy or saves energy consumption .
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- 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)
- Chemical Or Physical Treatment Of Fibers (AREA)
Abstract
Disclosed are reactive antibiotics comprising reactive groups bonded to sulfadiazine having strong anti-bacterial properties, the reactive groups of which are covalently bondable to natural fibers and rayon fibers, and a process of preparing the same. The present invention provides the reactive antibiotics covalently bondable to natural fibers and rayon fibers to give anti-bacterial properties to the fibers without adverse effect to color of the fibers, so that it can produce a functional fabric product that inhibits inhabitation or growth of microorganisms and, as a result, protects against infectious disease and bad odor, and prevents staining and brittleness of fiber of the fabric product.
Description
REACTIVE ANTIBIOTICS AND A METHOD OF PREPARING THE SAME AND ANTIBACTERIAL FIBER TREATED THEREBY
TECHNICAL FIELD The present invention relates to reactive antibiotics comprising reactive groups bonded to sulfadiazine (that is, 4-amino-N-2- pyrimidinylbezene sulfonamide) having strong anti-bacterial properties, the reactive groups of which are covalently bondable to natural fibers and regenerated fibers such as cotton, rayon, wool, polyvinylalcohol fiber, Lyocell, etc., a process of preparing the same and antibacterial fibers treated with the same.
Generally, a fabric product used in garment or bedclothes needs to undergo a fiber material dyeing process with desired colors to satisfy different tastes of consumers. Such manufactured fabric product often becomes habitable for microorganisms due to poor care, allowing the microorganisms to inhabit and grow with normal bodily secretions as nutrient when the microorganisms contact directly with a human body so that it threatens health of the human body and/ or results bad odor, contamination, discoloration, brittleness of fiber, etc., thereby being a major cause to deteriorate quality of the fabric product such as durability, color fastness or the like.
Accordingly, the fabric product may become a medium or habitat for pathogenic bacteria to invade the human body. However, if the fabric product has anti-bacterial properties, it will become a
functional fabric product that inhibits inhabitation or growth of microorganisms and, as a result, protects against infectious disease and bad odor, and prevents staining and brittleness of fiber of the fabric product.
BACKGROUND ART
It is well known that an ti- bacterial and deodorization processes are generally classified into post-treatment processes and fiber improving processes. The post-treatment processes include: as disclosed in Korean Patent Laid-Open No. 2000-007593, a method for giving anti-bacterial properties to fibers, which includes extraction of dyeing ingredient from a natural material such as Saururus chinensis (Lour.) Baill with anti-bacterial properties; a method which cross-links an anti-bacterial material such as organometallic compound or organic material with fibers and thermally fixes the bonded product to surface of the fibers by using a reactant resin; a method which fixes an antibacterial material to surface of fibers by adsorption and so on. On the other hand, the fiber improving processes include: a method which comprises introducing an inorganic anti-bacterial agent within fibers by blend- spinning the inorganic anti-bacterial agent into polymer in a process of manufacturing synthetic fibers; a method which disperses a copper compound into fibers during coagulating and regenerating in a process of manufacturing regenerated fibers; a method for synthesizing polymer, which comprises organic copolymer ingredients with anti- bacterial properties and so on.
The anti-bacterial and deodorization processes have not a purpose of sterilization or treatment of diseases but are to inhibit inhabitation and growth of microbes and/or fungi on fibers. Therefore, the processes require that an anti-bacterial effect is continuously maintained at least a predetermined level rather than only exhibiting high anti-bacterial properties for a short time and must safe to human bodies. Under these circumstances, although organic mercury compound, organic tin compound, organic copper compound and organic zinc compound among the organometallic compounds used in the post- treatment processes have very superior anti-bacterial properties, they also have a problem of safety to a human body such as toxicity. As a result, most of the organometallic compounds for garments are prohibited by countries such as Japan, U.S.A., etc. but are partially used in applications that do not involve direct contact with the human body, for example, production of carpet or wallpaper, or other industrial fields. Furthermore, such organometallic compounds that have demonstrated problems of undesired adhesion to fibers and low laundry durability are restricted in their permanent anti-bacterial effect. Also, general organic anti-bacterial materials that could be easily processed compared with inorganic materials and do not affect mechanical properties, transparency, color, etc., as much are widely used at present. However, use of the organic anti-bacterial materials is limited because their anti-bacterial effect is not continued for a long term as described above and they have inferior heat-resistance.
Alternatively, some of the organic anti-bacterial materials often have disadvantages of causing skin irritation, tearing property and so on. Dyes extracted from natural materials have a merit that anti-bacterial properties are early given to fibers in a dyeing process. But, they have a restriction in extracting the dyes due to seasonal limitation and a disadvantage that mordant dyeing accompanied with additional heavy metals is required to improve color fastness as a defect of natural dyes.
Inorganic anti-bacterial materials are obtained by substitution of an inorganic carrier such as zeolite, silica, alumina, etc. with metal ions such as copper, zinc, etc. having excellent anti-bacterial properties. The inorganic anti-bacterial materials that have three-dimensional structure formed with micro-fine pores demonstrate a large surface area and excellent heat- resistance. It is believed as of now that copper and zinc belong to a few metals with superior anti-bacterial effect and safety, and are harmless to the human body. The inorganic anti-bacterial materials have higher heat-resistance and stability sufficient not to cause volatilization and decomposition thereof in comparison to conventional organic anti-bacterial materials, thereby being used in a wide variety of applications. In addition, since they express anti-bacterial effect via activated oxygen ions, the inorganic anti-bacterial materials have an excellent anti-bacterial effect superior to the organic anti-bacterial materials. However, such metal ions, for example, copper or zinc that are apt to deteriorate resin or cause yellowing have a possibility of significantly lowering value of goods containing the same. There is another concern with the inorganic anti-bacterial materials in that they
may cause cutting of thread if the inorganic anti-bacterial materials are added to micro-fine fibers during blend-spinning, since they generally have a larger average particle diameter above micron units and a wider distribution of particle size. Korean Patent Laid-Open No. 2002-57322 discloses a reactive azo dye with strong anti-bacterial ability prepared by introducing silver sulfadiazine group, which is anti-bacterial component, into reactive azo dye molecules.
However, such known reactive azo dyes have low reaction yield when the reactive azo dye molecules react with silver sulfadiazine, are not applicable to endow anti-bacterial properties to fabric requiring no dyeing process, and need dyeing temperature raised to 98°C when they dye cotton fiber although the cotton fiber is sufficiently dyed at 600C, since the azo dyes have reaction temperature of about 98°C. Accordingly, the above azo dyes have a serious problem of severe energy waste.
DISCLOSURE OF THE INVENTION
(TECHNICAL PROBLEM) An object of the present invention is to provide reactive antibiotics that give anti-bacterial and anti-fungal properties to a fabric product while not dyeing the product with specific color, have lowered reaction temperature of about 600C and prevent undesirable waste of energy when the dyes are used to dye natural fibers such as cotton or wool, or rayon fiber, and a process of preparing the same.
(TECHNICAL MEANS TO SOLVE THE PROBLEM)
Hereinafter, the present invention will be described in detail.
A reactive antibiotic of the present invention has a structure of reactive groups represented by the following chemical formula 1 bonded to sulfadiazine having strong anti-bacterial and anti-fungal properties, the reactive groups of which are covalently bondable to natural fibers and rayon fibers.
(Chemical formula 1)
Sulfadiazine is sulfa drug effective for treating and protecting infectious diseases including, for example, meningitis caused by
Haemophilus influenzae, chancroid, acute urinary track disease, lymphoganuloma venereum caused by chloroquine-resistant plasmodia, early onset of falciparum malaria and so on.
A process of preparing the reactive antibiotics represented by the chemical formula 1 according to the present invention will be described in detail below.
First, sulfadiazine represented by general formula 1 is dissolved in water and maintained at 0 to 5°C. In an alternative beaker, cyanuric chloride represented by general formula 2 is treated as same to sulfadiazine represented by the general formula 1. After a constant time, the cyanuric chloride solution is slowly added to the sulfadiazine
solution to proceed condensation and synthesize the reactive antibiotics represented by the chemical formula 1
(General formula 1) Sulfa based antibiotic
(General formula 2) Cyanuric chloride
(Chemical formula 1)
(ADVANTAGEOUS EFFECTS)
As described in detail above, the inventive antibiotic can form covalent bond with natural fibers and rayon fibers to give anti-bacterial and anti-fungal properties to the fibers without adverse effect to color of the fibers.
If the present reactive antibiotic is employed in a fiber dyeing process, it does not require increase of dyeing temperature above normal dyeing temperature in order to proceed covalent bonding process between the antibiotic and fibers, since the reactive antibiotic
has reaction temperature lower than typical dyeing temperature of natural fibers and rayon fibers. Consequently, it results in a simple dyeing process and prevents waste of energy or saves energy consumption.
BEST MODE FOR CARRYING OUT THE INVENTION
Features of the present invention described above and other advantages will be more clearly understood by the following non-limited examples, which are not intended to restrict the scope of the invention but are instead illustrative embodiments of the present invention. Accordingly, it will be obvious to those skilled in the art that the present invention is not restricted to the specific matters stated above and the examples below.
[Example 1 : Preparation of a reactive antibiotic represented by the chemical formula 1]
0.01 moles of cyanuric chloride represented by the general formula 2 is mixed with small amount of acid, fed into 100ml of distilled water under agitation, and uniformly dispersed in the distilled water while maintaining the dispersion at 3°C. Alternatively, 0.01 moles of sulfadiazine represented by the general formula 1 is fed into distilled water, mixed with small amount of acid and dissolved in the distilled water while maintaining the solution at 3°C. The sulfadiazine solution is slowly added to the cyanuric chloride solution to proceed condensation for 2 hours. After completing the reaction, the obtained solution is subjected to cooling, neutralization and water removal, and dried under
vacuum conditions to produce the reactive antibiotic represented by the chemical formula 1 :
0.1% o.w.f. solution is produced by using the prepared reactive antibiotic represented by the chemical formula 1 in water and glacial acetic acid is added thereto to obtain a dye solution anti-bacterially treated. To the treated solution, cotton fiber is introduced and treated at
400C for 30 minutes, soaped and dried to form antibacterial fiber.
Following experiment for determining anti-bacterial properties of the above treated antibacterial fiber, the result is shown in Table 1 below.
[Test of anti-bacterial properties]
Conditions of the test for determining anti-bacterial properties of the antibacterial fiber according to the present invention are as follows:
1. Test method : KSK 0693-2001
2. Test types of strain
1) Strain I : Straphylococcus aureus ATCC 6538
2) Strain II : Klebsiella pneumoniae ATCC 4352
3. Concentration of challenged strain of bacteria
1) Strain I : 1.3 x 105 numbers/ ml
2) Strain II : 1.5 x 105 numbers/ ml
TABLE 1
Test result for anti- bacterial properties of colored antibacterial fiber
INDUSTRIAL APPLICABILITY As described in detail above, the present inventive antibiotic can form covalent bond with natural fibers and rayon fibers to give antibacterial and anti-fungal properties to the fibers without adverse effect to color of the fibers.
If the present reactive antibiotic is employed in a fiber grinding process, it does not require increase of dyeing temperature above normal dyeing temperature in order to proceed covalent bonding process between the antibiotic and fibers, since the reactive antibiotic has reaction temperature lower than typical dyeing temperature of natural fibers and rayon fibers. Consequently, it results in a simple dyeing process and prevents waste of energy or saves energy consumption .
While the present invention has been described with reference to
exemplary embodiments thereof, it will be understood by those skilled in the art that various modifications and variations may be made therein without departing from the scope of the present invention as defined by the appended claims.
Claims
1. A reactive antibiotic represented by the following chemical formula 1: (Chemical formula 1)
2. A process of preparing a reactive antibiotic represented by the following chemical formula 1, obtained by carrying out condensation of sulfa based antibiotic represented by general formula 1 with cyanuric chloride represented by general formula 2:
(General formula 1) Sulfa based antibiotic 
wherein A is H or Ag (General formula 2) Cyanuric chloride
(Chemical formula 1) 
wherein A is H or Ag.
3. An antibacterial fiber processed by using the reactive antibiotic as defined in Claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/KR2007/000705 WO2008096918A1 (en) | 2007-02-09 | 2007-02-09 | 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 |
|---|---|---|---|
| PCT/KR2007/000705 WO2008096918A1 (en) | 2007-02-09 | 2007-02-09 | Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby |
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Family
ID=39681809
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016187236A1 (en) * | 2015-05-15 | 2016-11-24 | University Of Massachusetts | Preparation and use of silver sulfadiazine-immobilized fillers |
| CN109576989A (en) * | 2018-11-06 | 2019-04-05 | 杭州旭富康科技有限公司 | A kind of preparation method of antibiotic cotton fiber |
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| WO2003066030A2 (en) * | 2002-02-07 | 2003-08-14 | Pharmacia Corporation | Pharmaceutical tablet |
| US20040214752A1 (en) * | 2002-12-19 | 2004-10-28 | Britten Nancy Jean | Dispersible pharmaceutical compositions |
| EP1330164B1 (en) * | 2000-10-09 | 2005-12-07 | Korea Research Institute of Chemical Technology | Antibacterial agents and antibacterial and deodorizing solution comprising the same |
| KR20060034334A (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 |
| KR20070029955A (en) * | 2005-09-12 | 2007-03-15 | 주식회사 코오롱 | Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby |
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2007
- 2007-02-09 WO PCT/KR2007/000705 patent/WO2008096918A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1330164B1 (en) * | 2000-10-09 | 2005-12-07 | Korea Research Institute of Chemical Technology | Antibacterial agents and antibacterial and deodorizing solution comprising the same |
| WO2003066030A2 (en) * | 2002-02-07 | 2003-08-14 | Pharmacia Corporation | Pharmaceutical tablet |
| US20040214752A1 (en) * | 2002-12-19 | 2004-10-28 | Britten Nancy Jean | Dispersible pharmaceutical compositions |
| KR20060034334A (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 |
| KR20070029955A (en) * | 2005-09-12 | 2007-03-15 | 주식회사 코오롱 | Reactive antibioties and a method of preparing the same and antibacterial fiber treated thereby |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016187236A1 (en) * | 2015-05-15 | 2016-11-24 | University Of Massachusetts | Preparation and use of silver sulfadiazine-immobilized fillers |
| US20180125763A1 (en) * | 2015-05-15 | 2018-05-10 | University Of Massachusetts | Preparation and use of silver sulfadiazine-immobilized fillers |
| US10736821B2 (en) * | 2015-05-15 | 2020-08-11 | University Of Massachusetts | Preparation and use of silver sulfadiazine-immobilized fillers |
| CN109576989A (en) * | 2018-11-06 | 2019-04-05 | 杭州旭富康科技有限公司 | A kind of preparation method of antibiotic cotton fiber |
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