US3542504A - Biocidal textile finishing - Google Patents

Biocidal textile finishing Download PDF

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Publication number
US3542504A
US3542504A US592346A US3542504DA US3542504A US 3542504 A US3542504 A US 3542504A US 592346 A US592346 A US 592346A US 3542504D A US3542504D A US 3542504DA US 3542504 A US3542504 A US 3542504A
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Prior art keywords
acid
fabric
solution
water
biocidal
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Expired - Lifetime
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US592346A
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English (en)
Inventor
Arthur Schofield
John B Lawton
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CALICO PRINTERS ASS Ltd
CALICO PRINTERS' ASSOCIATION LTD
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CALICO PRINTERS ASS Ltd
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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
    • 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
    • D06M11/07—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 halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
    • D06M11/11—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 halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
    • D06M11/155—Halides of elements of Groups 2 or 12 of the Periodic Table
    • 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
    • D06M11/58—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 nitrogen or compounds thereof, e.g. with nitrides
    • D06M11/64—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 nitrogen or compounds thereof, e.g. with nitrides with nitrogen oxides; with oxyacids of nitrogen or their salts
    • D06M11/65—Salts of oxyacids of nitrogen
    • 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
    • D06M11/68—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 phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof
    • D06M11/72—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 phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof with metaphosphoric acids or their salts; with polyphosphoric acids or their salts; with perphosphoric acids or their salts
    • 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
    • D06M11/83—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 metals; with metal-generating compounds, e.g. metal carbonyls; Reduction of metal compounds on textiles
    • H—ELECTRICITY
    • H03—ELECTRONIC CIRCUITRY
    • H03K—PULSE TECHNIQUE
    • H03K17/00—Electronic switching or gating, i.e. not by contact-making and –breaking
    • H03K17/51—Electronic switching or gating, i.e. not by contact-making and –breaking characterised by the components used
    • H03K17/78—Electronic switching or gating, i.e. not by contact-making and –breaking characterised by the components used using opto-electronic devices, i.e. light-emitting and photoelectric devices electrically- or optically-coupled
    • H—ELECTRICITY
    • H03—ELECTRONIC CIRCUITRY
    • H03K—PULSE TECHNIQUE
    • H03K5/00—Manipulating of pulses not covered by one of the other main groups of this subclass
    • H03K5/01—Shaping pulses
    • H03K5/04—Shaping pulses by increasing duration; by decreasing duration
    • H—ELECTRICITY
    • H03—ELECTRONIC CIRCUITRY
    • H03K—PULSE TECHNIQUE
    • H03K5/00—Manipulating of pulses not covered by one of the other main groups of this subclass
    • H03K5/13—Arrangements having a single output and transforming input signals into pulses delivered at desired time intervals
    • H—ELECTRICITY
    • H04—ELECTRIC COMMUNICATION TECHNIQUE
    • H04Q—SELECTING
    • H04Q1/00—Details of selecting apparatus or arrangements
    • H04Q1/18—Electrical details
    • H04Q1/30—Signalling arrangements; Manipulation of signalling currents
    • H04Q1/32—Signalling arrangements; Manipulation of signalling currents using trains of dc pulses
    • H04Q1/36—Pulse-correcting arrangements, e.g. for reducing effects due to interference

Definitions

  • the acid groups to which the biocidal metals are chemically combined may be introduced into the textile material formed at least in part of natural or regenerated cellulose and containing hydroxyl groups in a variety of ways in cluding the following:
  • Halogenated derivatives of mono and polybasic organic acids can be made to react with the hydroxy groups of the cellulose, in the presence of alkalies, to form cellulose carboxy alkyl ethers.
  • Polybasic organic acids of suitable acidity can be made to react with the cellulose hydroxyl groups by direct esterification, in such a Way that one of the acid groups is esterified, while leaving an acid group free.
  • Some polybasic inorganic acids can also be partial- 1y esterified with the cellulose hydroxyl groups in a similar manner. Owing to the high ionic strength of some of these acids and the marked degrading action which they have on cellulose polymers, esterification in these cases is carried out using special techniques.
  • biocidal metals which may be advantageously used in these new fabric treating methods are silver, copper, mercury, lead, beryllium, antimony and cadmium.
  • the washing procedure is repeated as many times as is desired.
  • Example 1 A plain-Weave cotton fabric 80/80, 30 /30 which has been bleached and mercerized was immersed in the following solutions, mangled to 100% pick-up, and dried at 70 C. The dried material was heat-treated under the stated conditions, washed in cold running water, then in 5 g./l. sodium carbonate solution for 2 minutes at 85 C. and again in cold running Water, squeezed and dried. The number of hydrogen ions per 100 anhydro glucose resigues in the samples were then determined as described elow.
  • the wet cloth can be left to lie at room temperature for some time to allow the reaction between the cellulose and the halogenated acid to take place or the reaction can be speeded up by steaming the fabric or by drying it at an elevated temperature. The treated fabric is then wellwashed in water to remove unreacted reagents and dried.
  • Example 2 A plain-weave cotton fabric, which had been bleached and mercerized was immersed in a solution of 12 g. sulfuric acid (98%), 63 g. urea and g. water, mangled to give a pick-up of 120%, dried at 100 C. and heattreated for 10 minutes at 170 C. The material was washed in cold running water, then in a 5 g./l. sodium carbonate solution for 2 minutes at 85 C., and again in cold running water, squeezed and dried. The treated material was then paded through a 0.5% solution of mercuric chloride, dried, washed off in cold running water and again dried. A portion of the treated material was washed in soap and soda for minutes at 93 C. and bactericidal tests made on the material before and after this laundering treatment. A halo of 5.5 mm. was shown by the unlaundered material and a halo of 4.0 mm. by the laundered material.
  • Example 3 A portion of cotton fabric as in Example 2 was immersed in an aqueous solution containing 16.5 gm. sodium hexametaphosphate and 59 g. of urea per 100 cc., mangled to give a pick-up of 100%, dried at 100 C. and heattreated for 10 minutes at 160 C. After this, it was washed in cold running water, then in 5 g./l. sodium carbonate solution for 2 minutes at 85 C., and again in cold running water, squeezed and dried. The treated material was then padded through a 0.5% solution of silver nitrate, dried, washed off in cold running water and again dried.
  • a portion of the treated material was washed in soap and soda for 30 minutes at 93 C., and bactericidal tests made on the material before and after this laundering treatment.
  • a halo of 2.0 mm. was shown by the unlaundered material and a halo of 1.5 mm. by the laundered material.
  • Example 4 Mercerized cotton cloth was immersed in a solution of 9 g. phosphoric acid (sp. gr. 1.75), 25 g. urea and 66 g. water, mangled to give a pick-up of 100%, dried at 100 C., heat-treated for 10 minutes at 160 C. and washed off in Water. Portions of the treated material were immersed in 0.5 solutions of (a) cadmium chloride, (b) mercuric chloride, (0) lead nitrate, and (d) copper sulfate for 30 minutes at room temperature and then washed ofi in cold running water to remove any unfixed metal salt. Separate samples of the treated material were then separately Washed in (1) 5 g./l. soap plus 2 g./l.
  • Example 5 A spun viscose cloth was immersed in a solution of 8 g. phosphoric acid (sp. gr. 1.75), 60 g. urea and 32 g. water, mangled to give a pick-up of 100%, dried at 100 C., heat treated for 2 minutes at 170 C. and washed off in cold running water, then in 5 g./l. sodium carbonate solution for 2 minutes at C. and again in cold running water, squeezed and dried. The material contained 20.5 hydrogen ions per anhydro glucose residues. It was then immersed in 20 times its weight of a 0.1 N solution of cadmium chloride for 1 hour at room temperature and then washed for 10 minutes in cold running water and dried.
  • 8 g. phosphoric acid sp. gr. 1.75
  • 60 g. urea 60 g. urea
  • 32 g. water mangled to give a pick-up of 100%, dried at 100 C., heat treated for 2 minutes at 170 C. and washed off
  • a sample of the treated material was washed in 5 g./l. soap, plus 0.2 g./l. sodium salt of ethylene diamine tetra-acetic acid on a wash-wheel for 1 /2 hours at 60 C., using a. liquor to goods ratio of 10: 1.
  • a halo of 16 mm. was shown by the unlaundered material and a halo of 9 mm. by the laundered material.
  • Example 6 The bactericidal effect of various metals absorbed onto mercerized cotton cloth containing 10 hydrogen ions per 100 anhydro glucose units, was evaluated by immersing the fabric in a solution of 9 g. phosphoric acid (sp. gr. 1.75), 25 g. urea and 66 g. water, mangling to give a pick-up of 100%, drying at 100 C., heat-treating for 10 minutes at 160 C., and washing off in water. The adsorption of the metal took place by immersing samples of the acid treated fabric in 0.5% solutions of a suitable salt of the metal for 30 minutes at room temperature, followed by washing in cold running water to remove excess metal-salt solution. The samples were washed in soap and soda at 93 C. for 30 minutes before examining the bactericidal properties.
  • 9 g. phosphoric acid sp. gr. 1.75
  • 25 g. urea 25 g. urea
  • 66 g. water mangling to give a pick-up
  • Salt solution Width of halo in mm. Silver nitrate 2.2
  • Example 7 An evaluation of the number of hydrogen ions per 100 anhydro glucose units of cellulose chain obtainable by treatment of cotton fibers was made with various acids as reported below:
  • Example 8 Mercerized cotton cloth was immersed in a solution of 18 g. maleic acid, 52 g. urea and 30 g. water, mangled to give a pick-up of 100%, dried at 100 C, heat-treated for 10 minutes at 130 C., and washed off in water. The treated material was then padded through a 0.5% solution of lead nitrate, dried, washed off in cold running water and again dried. A portion of the treated material was washed in soap and soda for 30 minutes at 93 C. and bactericidal tests made on the material before and after this laundering treatment. A halo of 3.5 mm. was shown by the unlaundered material and a halo of 2.5 mm. by the laundered material.
  • the determination of the number of acid groups which have been introduced into the textile material was performed by first immersing a sample of the treated material in a normal solution of hydrochloric acid at room temperature for 5 minutes, in order to ensure that all the introduced groups are present as the free acid, and then removing all traces of hydrochloric acid by a thorough washing in water.
  • the sample of cloth was then dried and a. weighed amount of it immersed in an aqueous solution of 0.1 normal potassium iodate and 0.5 N potassium iodide for 1 hour at room temperature and the liberated iodine, which is proportional to the number of acid groups on the Weighed sample of cloth, determined by titration with sodium thiosulfate.
  • the results are expressed in the form: number of hydrogen ions per 100 anhydro glucose units of the cellulose chain.
  • the determination of the bactericidal properties of the finish was carried out by the well-known Agar-Plate method, using Staphylococcus aureus as the test bacteria. For this, -20 ml. of a nutrient agar were innoculated with 1 ml. of a 24 hours-old broth culture of the bacteria and the mixture poured into a sterile petri dish. One inch diameter discs of the textile material were placed on the surface of the solidified agar and the assembly incubated for 24 hours at 37 C. The effectiveness of the bactericidal finish on the sample was assessed by measuring the width in millimeters of the growth-free clear zone or halo surrounding the disc of fabric.
  • the new methods of the invention are particularly suitable for finishing of textile materials formed in whole or in part of cellulosic fibers.
  • the benefits of the new methods are contemplated for use with fabrics made of other textile fibers which may contain hydroxyl groups reactive with acids or acid containing reagents in accordance with the described procedures.
  • the new methods are advantageously employed with fabrics made from cotton, linen, viscose rayon or mixtures of these as well as fabrics containing blended yams of cellulosic fibers and non-cellulosic fibers.
  • the fabrics treated by the new methods may be formed of mixtures of cellulosic fibers and non-cellulosic fibers, e.g., polyolefin, acrylic, modacrylic, polyester and equivalent fibers.
  • Textile materials treated in accordance with the methods may be in the form of non-woven fabrics, woven fabrics, knitted textiles or any other similar webs made up basically of thread-like fibers.
  • the textile material may be in the form of loose fiber, yarn or the like which will be subsequently converted into fabrics or ropes, twine, cordage and the like.
  • the chemical reagent employed for creating acid groups fixed to cellulosic fiber molecules in accordance with the invention may take a variety of forms. As illustrated in the foregoing examples, such reagents may be selected halogen derivatives of organic acids, polybasic organic acids, polybasic inorganic acids and salts of polybasic inorganic acids.
  • a preferred method of fixing acid groups to the fiber molecules of which the cellulosic textile material is formed involves the use of polybasic caids. Three features govern the choice of acid for this purpose:
  • the acid itself should be stable at the temperature needed to bring about the reaction with the cellulose
  • the dissociation constant of the first hydrogen ion of the acid should be great enough to allow reaction with the cellulose to take place in a reasonable time at a temperature which is not too high to cause substantial degradation of the celluolse, and
  • the dissociation constant of another hydrogen ion should be considerably lower than that of the first hydrogen ion so that little or no reaction between the cellulose and this other hydrogen ion takes place under the conditions required to bring about a reaction between the cellulose and the first hydrogen ion.
  • the attainment of these conditions and poly-basic acids suitable therefor can he readily determined by those skilled in the textile treatment art utilizing the general principles as stated and the method of determining number of acid groups which were introduced into the textile material as previously described. Although it mya be found that some acids outside these limits can be successfully employed, it has been found advantageous to utilize polybasic acids which are stable up to a temperature of at least 200 C. and which have a pK value for the dissociation constant of the first hydrogen of the acid at 25 C. not greater than 3.0 and the pK value of another hydrogen of the acid greater than about 4.0-.
  • polybasic acids for use in the new finishing methods include maleic, oxalic, citraconic, malonic, and phosphoric acids.
  • sulfuric acid may also be used.
  • halo-organic acids examples include monochloracetic, dibromosuccinic and equivalent acids. Salts of these acids with alkali metals or other bases may also be used for this purpose.
  • Concentrations of reagents and the reaction conditions may be varied and will be governed in part by the particular textile material being treated and the acid group fixing reagents employed. Optimum concentrations and other variables may be determined by simple testing using the test methods described above, or their equivalent, and the general principles as outlined. Introduction of between about 2 to 50 hydrogen ions per anhydro glucose units in the fiber molecules is advantageous. T0 attain this, elevated temperatures are preferably used with the polybasic acids or their salts, namely, 100 to 180 C. for times of treatment between about 1 to 30 minutes, shorter times generally being used the higher the temperature and/ or the lower the pK value of the acid.
  • Aqueous solutions of the acid fixing reagents are advantageously used and these can be of concentration between about 1 and 50 percent.
  • the solution also contain a weak organic base, e.g., a base having a pK value greater than about 10.0 such as urea.
  • the concentration of such base in the treating solution should be substantial, e.g., 10 to 350 parts or even higher of base per hundred parts of water and, in terms of the acid fixing reagent, 2 to 30 parts of base for each part of the acid or acid salt.
  • the amount of treating solution applied to the fabric may be varied and will be controlled in part by the percentage of cellulosic fibers in the textile material, acid fixing reagent, etc. With solutions containing 1 to 50% acid or acid salt, a solution pick-up before the drying and heating operation of 50 to 120% is advantageous.
  • the new operations can be used in conjunction with other textile processing procedures if this appears desirable or advisable, taking into account the end use of the fabric.
  • the textile material is treated in the form of yarns or filaments, the treatment will be succeeded by such operations as brading, rope twisting, weaving, knitting or the like.
  • Conjunctive operations may also include water-proofing embossing, dimension stabilizing, pressing and the like.
  • Application of other finishing and/ or treating agents can also be accomplished in conjunction with the new operations, e.g., application of sizing agents, softeners, lubricating materials, water-repellant agents, moth-proofing agents, mildew-proofing agents, dyes, pigments and the like.
  • Treated fabrics to be obtained in accordance with the invention are characterized by bactericidal and fungicidal properties which have very good resistance to laundering even in the presence of metal sequestering agents. Such qualities make the new textile materials particularly useful in humid tropic environments Where biocidal attack on textile materials is relatively great although the new treated textiles can be used for any other purposes for which resistance to biocidal attack are known or may become known to be useful.
  • a method of producing on a cellulosic fabric a bactericidal finish that is resistant to laundering with detergent solutions containing metal sequestering agents which comprises:
  • a method as claimed in claim 1 wherein said chemical bonding is accomplished by esterification of hydroxy groups of said fiber molecules by heating the fabric in an aqueous solution of a water-soluble salt of phosphoric acid at a temperature between about 100 and C.
  • step (A) is performed by immersing a fabric formed at least in part of cotton fibers in an aqueous solution containing 16.5 parts of sodium hexametaphosphate and 59 parts of urea per 100 parts of water, expressing solution from the impregnated fabric to give a solution pickup of 100% based upon the dry weight of the fabric, then drying the fabric
  • aqueous solution containing 16.5 parts of sodium hexametaphosphate and 59 parts of urea per 100 parts of water
  • expressing solution from the impregnated fabric to give a solution pickup of 100% based upon the dry weight of the fabric

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Nonlinear Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Computer Networks & Wireless Communication (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
US592346A 1965-11-11 1966-11-07 Biocidal textile finishing Expired - Lifetime US3542504A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB47829/65A GB1096736A (en) 1965-11-11 1965-11-11 Improvements in textile finishing

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US3542504A true US3542504A (en) 1970-11-24

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US592346A Expired - Lifetime US3542504A (en) 1965-11-11 1966-11-07 Biocidal textile finishing

Country Status (8)

Country Link
US (1) US3542504A (fr)
BE (1) BE689365A (fr)
BR (1) BR6684499D0 (fr)
DE (1) DE1594961A1 (fr)
ES (1) ES333228A1 (fr)
FR (1) FR1504077A (fr)
GB (1) GB1096736A (fr)
NL (1) NL6615947A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4525410A (en) * 1982-08-24 1985-06-25 Kanebo, Ltd. Particle-packed fiber article having antibacterial property
US4675014A (en) * 1984-03-06 1987-06-23 Henkel Kommanditgesellschaft Auf Aktien Microbistatic and deodorizing catamenial and hygienic devices
WO2022019960A1 (fr) * 2020-07-21 2022-01-27 Dan Dee International Holdings, Inc. Jouet doté de propriétés antimicrobiennes et son procédé de production

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3408131A1 (de) * 1984-03-06 1985-09-12 Chemiefaser Lenzing Ag, Lenzing Desodorierendes und mikrobistatisches fasermaterial
DE3418521A1 (de) * 1984-05-18 1985-11-21 Henkel KGaA, 4000 Düsseldorf Menstrualtampon

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2448153A (en) * 1946-09-10 1948-08-31 Us Agriculture Process of making cotton textiles water-absorbent and rotresistant
US2524783A (en) * 1948-04-02 1950-10-10 Bancroft & Sons Co J Method of imparting durable mildew resistance to fibrous cellulose materials

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2448153A (en) * 1946-09-10 1948-08-31 Us Agriculture Process of making cotton textiles water-absorbent and rotresistant
US2524783A (en) * 1948-04-02 1950-10-10 Bancroft & Sons Co J Method of imparting durable mildew resistance to fibrous cellulose materials

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4525410A (en) * 1982-08-24 1985-06-25 Kanebo, Ltd. Particle-packed fiber article having antibacterial property
US4675014A (en) * 1984-03-06 1987-06-23 Henkel Kommanditgesellschaft Auf Aktien Microbistatic and deodorizing catamenial and hygienic devices
WO2022019960A1 (fr) * 2020-07-21 2022-01-27 Dan Dee International Holdings, Inc. Jouet doté de propriétés antimicrobiennes et son procédé de production

Also Published As

Publication number Publication date
FR1504077A (fr) 1967-12-01
BR6684499D0 (pt) 1973-11-13
BE689365A (fr) 1967-04-14
NL6615947A (fr) 1967-05-12
DE1594961A1 (de) 1970-03-12
ES333228A1 (es) 1968-10-01
GB1096736A (en) 1967-12-29

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