Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
  • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
  • A61L2/20—Gaseous substances, e.g. vapours
  • A61L2/202—Ozone
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
• • 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
  • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
  • A01N59/16—Heavy metals; Compounds thereof
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
  • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
  • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
  • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
  • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
  • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
• • 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
  • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
  • D06P1/10—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes containing metal
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
  • A61L2202/10—Apparatus features
  • A61L2202/11—Apparatus for generating biocidal substances, e.g. vaporisers, UV lamps

Definitions

• the present invention relates to anti-bacterial agents based on sulfonamides as strong anti-bacterial reactant groups, and more particularly, to anti-bacterial acid dyes containing silver which are prepared by combining silver-containing sulfonamides with any of intermediates of dyes and a preparation method thereof, and an anti- bacterial fiber with a wide range of colors and improved anti-bacterial properties, which is produced by dyeing with the above silver-containing anti-bacterial acid dyes.
• a fabric product used in garment, bedding, etc. needs to undergo a fiber material dyeing process with desired colors to satisfy various tastes of consumer.
• Such manufactured fabric products often become 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 they threaten health of the human body and /or result 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 contagious disease and bad odor, and prevents staining and brittleness of fiber of the fabric 5 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
• 20 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 moth-proofing 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 also be 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 in countries such as Japan, U.S.A., etc.
• 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 can 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 given to fibers early in a dyeing process. But, they have a restriction in extracting the dyes due to seasonal limitation arid 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 silver, 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 silver, 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, silver, 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 have generally a larger average particle diameter above micron units and a wider distribution of particle size called 'fineness'.
• the present invention is directed to solve the problems of conventional anti-bacterial materials used as dyes as described above and, an object of the present invention is to provide an acidic dye containing strong anti-bacterial reactant groups and a preparation method thereof.
• an object of the present invention is to provide an acidic dye containing strong anti-bacterial reactant groups and a preparation method thereof.
• the present invention provides a method for preparing anti-bacterial acid dyes by introducing silversulfadiazine among sulfonamide based anti-bacterial agents with the excellent antibacterial function to precursors of acidic dyes.
• an anti-bacterial fiber with advantages, such as, that it needs no alternative process for obtaining anti-bacterial properties by dyeing the fiber with an anti-bacterial acid dye containing silver, exhibits no discoloring of woven fabric and/ or knitted fabric by decomposition of the dye, and demonstrates anti-bacterial properties and excellent durability for maintaining long term anti-bacterial effect for long term.
• an anti-bacterial acid dye represented by the following chemical formula 1 below, which has silver-containing sulfonamide as a diazo compound, and a preparation method thereof.
• the present invention provides an anti-bacterially functional fiber dyed by the above acid dye, which exhibits a wide range of colors and improved anti-bacterial properties simultaneously.
• R 1 is H, OH or NH 2 ;
• R2 is H, CH 3 or C 2 Hs;
• R3 and R 7 are independently H or Cl;
• R4 is H;
• R5 is H, SOsNa or SO3H; and
• Re is H, Cl, SO 3 Na or SO 3 H).
• Anti-bacterial materials include, for example, penicillin, sulfonamide, fluoroquinolone, tetracycline, aminoglucoside and the like. Among them, preferred are tetracycline, sulfonamide, quinolone, etc. which are widely and commercially available as intermediates of dyes.
• sulfonamide based anti-bacterial agents that endow anti-bacterial properties to a subject matter by inhibiting metabolism functions of enzymes in microorganisms such as synthesis of nucleic acid have been used in the present invention.
• Sulfonamide drug that is, the sulfonamide based anti-bacterial agent is one of anti-bacterial agents having SO2NH2 group and used as a general term for sulfanilamide derivatives that disrupt folic acid synthesis by the microorganisms.
• the above anti-bacterial agent is one of anti-bacterial materials that inhibit growth of bacteria including: for example, gram-positive cocci such as streptococci, pneumococci; gram- negative cocci such as meningococci, gonococci; gram-positive bacillus such as Escherichia coli, shigellae; and the like.
• Sulfonamide commonly has a molecular structure of sulfanilamide and includes varied kinds of compounds.
• Sulfonamide based anti-bacterial materials include, but are not limited to, sulfapyridine, sulfadiazine, silversulfadiazine, sulfamerazine, sulfamethoxine, sulfapyrazine, phthalylsulfathiazole, sulfa thiazole, mafenide, sulfadimidine, sulfamethazine, sulfamethoxazole, sulfanilamide, sulfamethoxypyridazine, sulfaguanidine, sulfadimethoxine, sulfisoxazole, sulfadoxine, sulfamethizole, sulphasalazine, sulphinpyrazone, etc.
• the present invention is applied to synthesis of anti-bacterial acid dyes by using silversulfadiazine(monosilver-4-amino-N- pyrimidylbenzene sulfonamide) represented by the following general formula 1 among sulfonamide based anti-bacterial agents containing silver that are mostly available as intermediates of dyes easily synthesized and exhibit excellent anti-bacterial effect:
• Silversulfadiazine is one of sulfadiazine derivatives, exhibits anti-bacterial properties against yeast as well as numerous gram- positive and gram-negative microorganisms and is used as a locally and externally applied anti-infectious disease agent effective to protect and treat sepsis of second and/ or third degree burns.
• a method for preparing the anti-bacterial acid dye containing silver represented by the following chemical formula 1 according to the present invention.
• the present invention provides the anti-bacterial acid dye represented by the following chemical formula 1 synthesized by (a) a first step of conducting diazotization of silversulfadiazine represented by the following general formula 1 with hydrochloric acid and sodium nitrite, and (b) a second step of proceeding azo-coupling reaction of the resulting product with 2,5-dichloro-4-(5-hydroxy-3-methyl-pyrazol-l- yl)-benzene sulfonic acid represented by the following general formula 2, or 3-(5-hydroxy-3-methyl-pyrazol-l-yl)-benzene sulfonic acid represented by the following general formula 3.
• General formula 1 silversulfadiazine
• R 1 is H, OH or NH 2 ;
• R2 is H, CH 3 or C 2 H 5 ;
• R3 and R 7 are independently H or Cl;
• R4 is H;
• R5 is H, SO 3 Na or SO 3 H; and
• Re is H, Cl, SO 3 Na or SO 3 H).
• a preferred embodiment of the present invention comprises an anti-bacterial acid dye containing silver represented by the following chemical formula 2 which is obtainable by: a first step of conducting diazotization of silversulfadiazine represented by the following general formula 1 among sulfonamide based anti-bacterial agents containing silver, as a dye intermediate, with hydrochloric acid and sodium nitrite; and a second step of combining the resulting product with 2,5-dichloro-
• Another preferred embodiment of the present invention comprises an anti-bacterial acid dye containing silver represented by the following chemical formula 3 which is obtainable by: a first step of conducting diazotization of silversulfadiazine represented by the following general formula 1 among sulfonamide based anti-bacterial agents containing silver, as a dye intermediate, with hydrochloric acid and sodium nitrite; and a second step of combining the resulting product with 3-(5-hydroxy-3-methyl-pyrazol-l-yl)-benzene sulfonic acid represented by the following general formula 3 through azo-coupling reaction.
• the anti-bacterial acid dye compounds of the present invention having yellow color can express a wide range of colors when they are used in combination, and be utilized to produce an anti-bacterially functional fiber product dyed by the same that exhibits strong anti-bacterial properties to inhibit inhabitation or growth of microorganisms and, as a result, protects against contagious disease and bad odor and prevents staining and brittleness of fiber of the fiber product.
• the present invention enables production of the anti-bacterial fiber product with advantages that it endows anti-bacterial properties early during a dyeing process, needs no alternative process for providing anti-bacterial properties, exhibits no discoloring of woven fabric and/ or knitted fabric caused by decomposition of dyes, and demonstrates antibacterial properties and excellent durability for maintaining anti- bacterial effect for a long term.
• reaction scheme 1 After dispersing 0.02 moles of silversulfadiazine in distilled water at 5°C or below, 6ml of hydrochloric acid HCl was added and dissolved while stirring. To the obtained solution, slowly added was 0.02 moles of sodium nitrite NaNO2 to proceed diazotization represented by the following reaction scheme 1 :
• reaction scheme 2 To this solution, slowly added was the diazo solution previously obtained to proceed azo-coupling reaction represented by the following reaction scheme 2:
• the resulting solution was titrated to adjust pH value to 7, filtered using a filter paper after salting out and dried to yield an anti-bacterial acid dye with yellow color represented by the chemical formula 2 above according to the present invention.
• reaction scheme 4 (Reaction scheme 4)
• the resulting solution was titrated to adjust pH value to 7, filtered using a filter paper after salting out and dried to yield an anti-bacterial acid dye with yellow color represented by the chemical formula 3 above according to the present invention.
• control sample nylon (KS K 0905-1996)
• non-ionic surfactant Tween 80 (0.05%)
• the anti-bacterial acid dye of the present invention having yellow color expresses a wide range of colors when two or more of the dyes are used in combination, and enables production of anti-bacterially functional fiber products dyed by the same that exhibit strong anti-bacterial properties to inhibit inhabitation or growth of microorganisms and, as a result, protect against contagious disease and bad odor and prevent staining and brittleness of fiber.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• General Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• Textile Engineering (AREA)
• General Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Plant Pathology (AREA)
• Inorganic Chemistry (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Biochemistry (AREA)
• Pest Control & Pesticides (AREA)
• Dentistry (AREA)
• Microbiology (AREA)
• Agronomy & Crop Science (AREA)
• Epidemiology (AREA)
• Animal Behavior & Ethology (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=36927628

Family Applications (1)

Country Status (2)

Citations (3)

• 2005
  • 2005-02-23 KR KR1020050014921A patent/KR100942198B1/ko active IP Right Grant
• 2006
  • 2006-02-23 WO PCT/KR2006/000623 patent/WO2006091023A1/en active Application Filing

Patent Citations (3)

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events