US3817702A - Antimicrobial textile materials - Google Patents

Antimicrobial textile materials Download PDF

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Publication number
US3817702A
US3817702A US00094532A US9453270A US3817702A US 3817702 A US3817702 A US 3817702A US 00094532 A US00094532 A US 00094532A US 9453270 A US9453270 A US 9453270A US 3817702 A US3817702 A US 3817702A
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US
United States
Prior art keywords
active
fabric
textile material
anion
acid
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Expired - Lifetime
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US00094532A
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English (en)
Inventor
W Paulus
O Pauli
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Bayer AG
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Bayer AG
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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
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/907—Resistant against plant or animal attack

Definitions

  • a cotton fabric is reacted with the chlorine atoms of p-N(4,6-dich1oro)-striazinylaminobenzene-carboxylic or -sulfonic acid and the acid group is thereafter reacted with a bactericidal quaternary ammonium salt or an N-chloro-phenyl-alkylene polyamine.
  • the resulting products are bactericidal, free from attack by mildew and suitable for autosterile surgical dressings.
  • the present invention relates to the antimicrobial finishing of textile materials, especially cellulose-containing textile material.
  • Textile articles are often prone to attack by microorganisms such as mildew, fungi, and the like, resulting in discoloration, odor and, frequently, destruction. Attempts have been made to overcome this problem by impregnation with various agents but this is often attended by a change in hand, e.g. stiffening, by its own change in color, loss of abrasion resistance, etc. Moreover, the treatment is not permanent, the agent being lost in washing or dry cleaning. It is accordingly an object of the present invention to provide textile materials which are resistant to microorganisms but retain all the usual desirable characteristics of textiles and which, further, permanently retain the desired properties.
  • Any textile material having a reactive hydrogen may be used for the instant purposes including cotton, rayon, paper, cellulose acetate, polyvinyl alcohol, wool, and the like, the cellulosics being especially preferred.
  • reactive ionic substances which can be linked chemically with the textile material, for example cotton, so that a lastingly, partially anion-active textile material is formed
  • the textile material for example cotton
  • p-N(4,6-dichloro-)s-triazinyl-aminobenzoic acid and p-N-(4,6-dichloro-)s-triazinyl-aminobenzene-sulfonic acid as well as monochloroacetic acid, chloromethylphosphonic acid and unsaturated aliphatic carboxylic acids, for example haloacrylic acids and acetylenemonoor dicarboxylic acid.
  • Such compounds aifix themselves to the textile base by losing their halogen atoms which react with the reactive hydrogen of the base or by condensation at the unsatu- 3,817,702 Patented June 18, 1974 without loss of anti-microbial effectiveness, bactericidal quaternary ammonium salts and N-chloro-phenyl-alkylenepolyamines are suitable; for example benzyl-dimethyltetradecylammonium chloride, 3,4-dichlorobenzyl-dimethyl-dodecylammonium chloride, N -pentachlorophenyl-N dimethylbenzyltrimethylenediaminium chloride, N -pentachlorophenyl-N -dimethyl-(3,4-dichloro)benzyl trimethylenediaminium chloride (cf. Deutsche Offenlegungschrift (German Published Specification) 1,493,745) and N pentachlorophenyl hexamethylenediamine acetate (cf
  • partially anion-active material for example, cotton fabric
  • the production of partially anion-active material can be effected by treating the fabric with a 2-5 strength alkaline-aqueous solution of the reactive ionic substances concerned, possibly with addition of an electrolyte (for example NaCl, Na SO for 10-40 minutes at 40-60 C. It is also possible to proceed by impregnating the fabric at room temperature with an alkaline-aqueous solution of the reactive ionic substances concerned, subsequently squeezing off and, possibly after a preliminary drying at about 70 C., thermofixing at l50 C.
  • an electrolyte for example NaCl, Na SO for 10-40 minutes at 40-60 C.
  • the subsequent fixation of the cation-active microbicide concerned may be effected by causing it to be absorbed by the alkaline-reacting, partially anion-active textile material from an aqueous solution for about half an hour at 50-60 C.; squeezing off may then be effected and the textile material freed from unfixed portions of active compound by washing.
  • the amounts of cation-active microbicides required for the lasting antimicrobial finishing of partially anion-active textile material are governed by what is demanded of the finish, and can in each case be readily ascertained by preliminary experiments; in general, 0.251% in the treatment bath is sufiicient.
  • the cation-active microbicides concerned are absorbed better and more lastingly on partially anion-active textile material than on normal textile material; the antimicrobial finish of textile material attainable with the aid of the process according to the invention is therefore distinguished by a particularly high fastness to washing.v
  • the textile materials produced in accordance with the invention are microbicidal since it might have been expected that the agents would lose their potency when tied to the textile material in salt formation.
  • certain hygiene problems such as may occur in textile materials, can be successfully solved.
  • the process is useful in the control of pathogenic bacteria and fungi, as well as in avoiding or reducing cross-infections during laundering or other cleaning.
  • the process according to the invention permits the production of autosterile dressings and other microbicidal textile material which can be used in hospitals, for example for wrapping sterilized surgical instruments, or in bacterio EXAMPLE 1
  • De-sized cotton fabric is treated at 40 C. with a suspension of 2% p-N-( 4,6-dichloro) s triazinylaminobenzoic acid (I) in water which also contains 0.05%
  • the fabric is soapecl at EXAMPLE 3
  • De-sized cotton fabric is impregnated (2 passages) at room temperature with a freshly prepared solution which, per liter contains 50 g. NaOH, 25 g. chloroacetic acid and 1 g. of a non-ionic wetting agent.
  • the fabric is subsequently dried at 120-140 C. for thermofix-ation and then transferred to a bath having a temperature of 55 C. and containing, per liter, 2.5 g. N -pentachlorophenylhexamethylenediamine acetate; liquor ratio 1: 15.
  • the pH of the bath is adjusted to 8.5 after introduction of the fabric.
  • EXAMPLE 4 De-sized cotton fabric is treated as stated in Example 3, with the difference that N -pentachlorophenyl-N -dimethylbenzyltrimethylene diaminium chloride is used g./liter) as cation-active compolmd and there is no regulation of pH. After rinsing, the fabric is, in the manner indicated in Example 1, watered and tested for resistance to rotting; the losses of resistance to tearing are, on average, 2% compared with 100% and 88% respectively, in the case of a fabric which was only partially carboxymethylated and a fabric which was only treated with the cation-active compound.
  • EXAMPLE 5 De-sized cotton fabric is treated and tested for resistance to rotting in the manner indicated in Example 3 except that, as cation-active compound, N -pentachlorophenyL-N- -dimethyl (3,4-dichloro) benzyltrimethylenediaminium chloride is used (5 g./liter). The losses of resistance to tearing are on average, 4%, compared with 82% in the case of a fabric which was only treated with the cation-active compound.
  • EXAMPLE 6 De-sized cottom fabric is treated as stated in Example 5, with difference that not 5 g./liter but 10 g./liter of cation-active compound are used. After rinsing and watering, the fabric is 12 times soaped at the boil or washed 12 times with a commercial cold-washing agent and then, in the manner indicated in Example 2, tested for anti-bacterial effectiveness. In both cases, the fabric still possesses a good anti-bacterial effectiveness. A fabric which was not carboxymethylated and was only treated with the cation-active compound, however, no longer shows any anti-bacterial effectiveness after soaping 5 times or cold-washing 5 times.
  • EXAMPLE 7 De-sized cotton fabric is impregnated (3 passages) at room temperature with a freshly prepared solution which contains per liter, 70 g. NaOH and 50 g. chloromethylphosphonic acid. After squeezing off, drying at ISO-140 C. is effected, followed by thermofixation for a further 5 minutes at 130-140" C., before the fabric is transferred for 30 minutes to a bath which, per liter, contains 10 g. benzyldimethyltetradecylammonium chloride. After rinsing and Watering twice in the manner indicated in Example 1, testing for resistance to rotting is effected: the tear value losses are, on average, 3%. As against this, a fabric treated only with chloromethylphosphonic acid or only with the cation-active compound rots completely loss of resistance to tearing).
  • EXAMPLE 8 De-sized cotton fabric is impregnated (3 passages) with a solution which, per liter, contains 200 g. NaOH, 50 g. acetylenedicarboxylic acid and 1 g. of a non-ionic wetting agent. After squeezing otf, drying at 100 C. is effected, followed by thermofixation for 10 minutes at 100 C. Treatment with cation-active compound is then carried out in the manner indicated in Example 2.
  • the fabric Before testing for rot resistance as indicated in Example l, the fabric is watered twice for 24 hours. The fabric proves to be so rot-resistant that no measurable loss of rot resistance occurs. Moreover, the fabric is outstandingly anti-bacterially effective, even after soaping 12 times with a non-ionic detergent; 4 times soaping at the boil with an anion-active detergent likewise does not adversely affect the anti-bacterial effectiveness.
  • the textile material can be rendered anion-active by a treatment in fabric form.
  • the treatment can be carried out on the textile in the form of a yarn or staple fibers.
  • synthetic fibers it is even posible to carry out the treatment at the resin stage or possible even during the formation of the resin as by copolymerization.
  • the treatment with the cationic microbicide can similarly be carried out at various stages of processing such as on finished garments, fabrics, yarns, fibers, resins or even monomers.
  • the cationic microbicide treatment can immediately follow the treatment to render the material anion-active or it can be carried out one or more steps later.
  • anion-active sites can be varied widely and the particular selection will depend upon the type and extent of microbicidal treatment desired.
  • its content of anion-active sites will have to be greater to impart the desired level of activity to the resulting product.
  • the degree of substitution should not be so great that the usual desirable properties of the textile material suffer unduly.
  • the eflicacy and purpose of the microbicidal agent attached to the anionactive site is also significant. Thus stronger agents can be utilized in lesser amounts; if it is merely desired to prevent growth of undesirable organisms a lesser amount is needed than if it is desired that the textile material actively attack undesired microorganisms in the vicinity.
  • microbicidal agent need not be employed in such quantity as will form salts with all of the anion-active sites, i.e. the desired level of microbicidal activity may be achieved with only some of the anion-active sites neutralized with microbicide.
  • microbicide is fixed to the anion-active textile material by being absorbed thereon from an aqueous solution in which the textile material is maintained at about 50-60" C., followed by squeezing 011 and washing ofi unfixed portions of active material.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US00094532A 1969-12-16 1970-12-02 Antimicrobial textile materials Expired - Lifetime US3817702A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1962899A DE1962899B2 (de) 1969-12-16 1969-12-16 Verfahren zur antimikrobiellen Ausrüstung von cellulosehaltigen! Textilmaterial

Publications (1)

Publication Number Publication Date
US3817702A true US3817702A (en) 1974-06-18

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ID=5753950

Family Applications (1)

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US00094532A Expired - Lifetime US3817702A (en) 1969-12-16 1970-12-02 Antimicrobial textile materials

Country Status (8)

Country Link
US (1) US3817702A (enrdf_load_stackoverflow)
BE (1) BE760411A (enrdf_load_stackoverflow)
CH (2) CH537696A (enrdf_load_stackoverflow)
DE (1) DE1962899B2 (enrdf_load_stackoverflow)
FR (1) FR2070889B1 (enrdf_load_stackoverflow)
GB (1) GB1295375A (enrdf_load_stackoverflow)
NL (1) NL7018137A (enrdf_load_stackoverflow)
SE (1) SE387669B (enrdf_load_stackoverflow)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4090844A (en) * 1977-06-23 1978-05-23 The United States Of America As Represented By The Secretary Of Agriculture Process of producing high performance durable-press cotton
US4259383A (en) * 1978-06-30 1981-03-31 Sterling Drug Inc. Disinfecting tissue
US4312981A (en) * 1980-04-01 1982-01-26 Wright State University Modified cellulosic products having enhanced thermal, solvent, and biological properties
US4447243A (en) * 1981-08-17 1984-05-08 Dixie Yarns, Inc. Odor scavenging system
EP0338173A1 (en) * 1988-04-22 1989-10-25 Ricoh Kyosan Inc. Ionic dressing for topical administration of drugs to wounds and burns
US5098417A (en) * 1990-04-12 1992-03-24 Ricoh Kyosan, Inc. Cellulosic wound dressing with an active agent ionically absorbed thereon
US5152996A (en) * 1990-12-10 1992-10-06 Eastman Kodak Company Nonwoven wipes impregnated with an aqueous solution of a zinc acetate peroxide and a surfactant
US5935383A (en) * 1996-12-04 1999-08-10 Kimberly-Clark Worldwide, Inc. Method for improved wet strength paper
WO2000015897A1 (en) * 1998-09-11 2000-03-23 The Regents Of The University Of California Antimicrobial treatment of polymers
US6475501B1 (en) 1997-06-04 2002-11-05 The Procter & Gamble Company Antiviral compositions for tissue paper
US6517849B1 (en) 1999-10-19 2003-02-11 The Procter & Gamble Company Tissue products containing antiviral agents which are mild to the skin
US6756076B2 (en) 2000-10-13 2004-06-29 Michael Brier Process for producing fabric articles having water-resistant and/or antimicrobial characteristics
US6962608B1 (en) 2002-10-01 2005-11-08 The Regents Of The University Of California Regenerable antimicrobial polymers and fibers with oxygen bleaches
US20090069210A1 (en) * 2006-03-14 2009-03-12 Henkel Ag & Co. Kgaa Colour-protecting laundry detergent composition
US20110171282A1 (en) * 2007-06-19 2011-07-14 Rynel Inc. Materials Comprising Water-Soluble Polymer Particles and Methods of Making and Using Them
US8263541B2 (en) 2005-08-19 2012-09-11 Henkel Ag & Co. Kgaa Triazine derivative dye transfer inhibitors, washing products containing the same and uses therefor
US9326504B1 (en) * 2015-06-23 2016-05-03 Christine Graziano Disposable antibacterial liner

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE574272A (enrdf_load_stackoverflow) * 1957-12-31
FR1499788A (fr) * 1966-11-16 1967-10-27 Mo Textilny I Procédé de préparation de produits doués de propriétés antimicrobiennes à partir de fibres ou pellicules

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4090844A (en) * 1977-06-23 1978-05-23 The United States Of America As Represented By The Secretary Of Agriculture Process of producing high performance durable-press cotton
US4259383A (en) * 1978-06-30 1981-03-31 Sterling Drug Inc. Disinfecting tissue
US4312981A (en) * 1980-04-01 1982-01-26 Wright State University Modified cellulosic products having enhanced thermal, solvent, and biological properties
US4447243A (en) * 1981-08-17 1984-05-08 Dixie Yarns, Inc. Odor scavenging system
EP0338173A1 (en) * 1988-04-22 1989-10-25 Ricoh Kyosan Inc. Ionic dressing for topical administration of drugs to wounds and burns
US5098417A (en) * 1990-04-12 1992-03-24 Ricoh Kyosan, Inc. Cellulosic wound dressing with an active agent ionically absorbed thereon
US5152996A (en) * 1990-12-10 1992-10-06 Eastman Kodak Company Nonwoven wipes impregnated with an aqueous solution of a zinc acetate peroxide and a surfactant
US5935383A (en) * 1996-12-04 1999-08-10 Kimberly-Clark Worldwide, Inc. Method for improved wet strength paper
US6475501B1 (en) 1997-06-04 2002-11-05 The Procter & Gamble Company Antiviral compositions for tissue paper
US6436419B1 (en) 1998-09-11 2002-08-20 The Regents Of The University Of California Antimicrobial treatment of polymers
WO2000015897A1 (en) * 1998-09-11 2000-03-23 The Regents Of The University Of California Antimicrobial treatment of polymers
US6517849B1 (en) 1999-10-19 2003-02-11 The Procter & Gamble Company Tissue products containing antiviral agents which are mild to the skin
US6756076B2 (en) 2000-10-13 2004-06-29 Michael Brier Process for producing fabric articles having water-resistant and/or antimicrobial characteristics
US20050014436A1 (en) * 2000-10-13 2005-01-20 Michael Brier Process for producing fabric articles having water-resistant and/or antimicrobial characteristics
US6962608B1 (en) 2002-10-01 2005-11-08 The Regents Of The University Of California Regenerable antimicrobial polymers and fibers with oxygen bleaches
US8263541B2 (en) 2005-08-19 2012-09-11 Henkel Ag & Co. Kgaa Triazine derivative dye transfer inhibitors, washing products containing the same and uses therefor
US8785362B2 (en) 2005-08-19 2014-07-22 Henkel Ag & Co. Kgaa Triazine derivative dye transfer inhibitors, washing products containing the same and uses therefor
US7947087B2 (en) * 2006-03-14 2011-05-24 Henkel Ag & Co. Kgaa Color transfer inhibitors, detergent compositions containing the same and uses therefor
US20090069210A1 (en) * 2006-03-14 2009-03-12 Henkel Ag & Co. Kgaa Colour-protecting laundry detergent composition
US20110171282A1 (en) * 2007-06-19 2011-07-14 Rynel Inc. Materials Comprising Water-Soluble Polymer Particles and Methods of Making and Using Them
US8962027B2 (en) 2007-06-19 2015-02-24 Rynel Inc. Materials comprising water-soluble polymer particles and methods of making and using them
US9326504B1 (en) * 2015-06-23 2016-05-03 Christine Graziano Disposable antibacterial liner

Also Published As

Publication number Publication date
BE760411A (fr) 1971-06-16
CH1864270A4 (enrdf_load_stackoverflow) 1972-12-29
DE1962899A1 (de) 1971-06-24
NL7018137A (enrdf_load_stackoverflow) 1971-06-18
CH537696A (de) 1972-12-29
FR2070889A1 (enrdf_load_stackoverflow) 1971-09-17
GB1295375A (enrdf_load_stackoverflow) 1972-11-08
FR2070889B1 (enrdf_load_stackoverflow) 1975-02-21
SE387669B (sv) 1976-09-13
DE1962899B2 (de) 1978-08-24
DE1962899C3 (enrdf_load_stackoverflow) 1979-04-19

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