US3087774A - Antimicrobial composition and process for applying same - Google Patents

Antimicrobial composition and process for applying same Download PDF

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Publication number
US3087774A
US3087774A US845663A US84566359A US3087774A US 3087774 A US3087774 A US 3087774A US 845663 A US845663 A US 845663A US 84566359 A US84566359 A US 84566359A US 3087774 A US3087774 A US 3087774A
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United States
Prior art keywords
zinc
fibers
antimicrobial
organic solvent
agent
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Expired - Lifetime
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US845663A
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Mendelsohn Meyer
Horowitz Carl
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Yardney International Corp
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Yardney International Corp
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Priority to US845663A priority Critical patent/US3087774A/en
Priority to GB33990/60A priority patent/GB920989A/en
Priority to ES0261492A priority patent/ES261492A1/en
Priority to CH1050362A priority patent/CH368657A/en
Priority to ES0268776A priority patent/ES268776A1/en
Application granted granted Critical
Publication of US3087774A publication Critical patent/US3087774A/en
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • 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 System
    • 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
    • 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/21—Nylon

Definitions

  • Our present invention relates to atreatment' of fabrics and other materials with metallic compounds designed to impart antimicrobial properties to 'such'materials.”
  • the treatmehtdis' closed in these pending applications involves theinimersion of the material'in an'aqueous bath at hight'eni peratures, the bath includingas its principal ingredients a chelating agent, a catalyst'su-ch as sodium acetate an'd optionally a detergent along with'za suitable zincfcompound such as zinc chloride:
  • a fixingagent rich in amine groups, such as urea is applied'to thernaterial' either" in the'sarne bath' or in a second treatment solution to help lock the zinc in place on the fibers.
  • an object of our present invention to provide an improved process for supplying such compositions to fibrous materials at ordinary temperatures and without the use of a slow-drying aqueous medium; a related object is to provide a modified antimicrobial composition adapted to be so applied.
  • a zinc salt a chelating agent, a catalyst, an aminating agent and preferably a detergent and buffering agent in an organic solvent, advantageously, a low-boiling ketone.
  • an organic solvent advantageously, a low-boiling ketone.
  • ketones found suitable for the process'of our invention, the lower-boiling ones being preferred because of their shorter drying time.
  • Trifluoro acetone-" 21 Acet s 56 Hexafluoroacetyl acetone; 63-65 Z-bntanone (ethyl methyl) B buten Z-one (methyl vinyl) 81 Biacetyl acetone 88 Methyl isopropyl ketone; 94.3 Diethyl acetone 1 02 Methyl propyl ketone 102.3 Pinacolone H V 106 Methyl isobutyl ketone 116.8 Cyclohexanone' 156' The folowing proportions (by weight) have been found to give a satisfactory mixture:
  • the zinc compound is preferably zinc chloride but may also be zinc sulphate or zinc nitrate.
  • Detergent such as ethylene cycloimido l-alkyl (fatty acid) 2-hydroxy ethylene sodium alcoholate methylene sodium carboxylate 10 17.5 grams of the above mixture together with 17.5 grams of urea crystals are dissolved in 1000 grams of acetone. The resulting solution is sprayed at room temperature by means of an atomizer onto a piece of cotton or wool textile and allowed to dry for about two minutes.
  • a sample of the textile so treated is washed 20 times in a household washing machine with soap or detergent and is then placed on a Petri dish containing agar streaked with a culture of Staphyl coccus aureus. After an incubation period of 24 hours a 2-mm. zone of inhibition is observed.
  • the zone of inhibition is found to be 3 mm.
  • Example 2 The same as Example 1, except that cyclohexanone is used as a solvent in place of acetone. The solution dries in about five minutes.
  • a l-mm. zone of inhibition against Staphylococcus aureus is observed after 20 washings.
  • Example 3 Methyl isobutyl ketone is used as a solvent in lieu of those given in Examples 1 and 2. The drying time is about three minutes. The same zone of inhibition is observed as in Example 2.
  • the concentration of the mixture of the aforedescribed solids in the organic solvent may vary from 0.1% to the saturation point, the latter being approximately 5%.
  • composition according to the invention can also be used successfully on synthetic fibers, such as nylon.
  • alkali-metal acetates such as potassium or 1ithium acetate, may be used as the catalyst in lieu of sodium acetate.
  • An antimicrobial treating composition comprising a zinc salt, an aminating agent and a chelating agent all distributed in a volatile organic solvent.
  • a composition according to claim 2 including as a catalyst an alkali-metal acetate.
  • composition according to claim 3 including a detergent.
  • composition according to claim 3 including a buffering agent.
  • textile fiber impregnated with a composition comprising a zinc salt, an aminating agent and a chelating agent all distributed in a volatile organic solvent.
  • textile fiber is selected from the group consisting of cellulosic, proteinaceous and nylon fibers.
  • An antimicrobial treating composition comprising a zinc salt selected from the group consisting of zinc chloride, zinc sulfate and zinc nitrate; urea; sodium ethylenediamine-tetraacetate and a volatile organic solvent.
  • a process for imparting antimicrobial properties to textile fibers comprising applying to said fibers a solution of a zinc salt, an aminating agent and a chelating agent dissolved in a volatile organic solvent and allowing said solution to dry whereby antimicrobial properties are imparted to said textile fibers.
  • a process for imparting antimicrobial properties to textile fibers comprising applying to said fiber a solution of a Zinc salt, a chelating agent dissolved in a volatile organic solvent, treating the fiber with an aminating agent and allowing said fiber to dry whereby antimicrobial prop erties are imparted to said textile fiber.

Description

United States Patent 3,087,774 ANTIMICROBIAL COMPDSITION AND PROCESS OR APPLYING S 1 Meyer, Mendelsohn, New York, and Carl Horowitz,
Brooklyn, NY., assignors; by nisne assignments, to Yardney lnternational Corp New York,jN.Y., a corporation of New York 7 s v No Drawing. Filed'0et.-12, 1959, Ser. No. 845,663
12 Claims. (Cl. 8'--115.5)
Our present invention relates to atreatment' of fabrics and other materials with metallic compounds designed to impart antimicrobial properties to 'such'materials." s
In co-pending applications Ser. Nos. 738,967 and 760,857, filed by Meyer Mendelsohn on June 2, 1958, and September 15, 1958, respectively, both now abandoned, there has been disclosed a" treatment of" this character in whicha'zinc compound is causedito react on the fibers of a material to be treated, notably a cellulosic or proteinaceous material sotha't the zinc will firmly adhere to the fibers and exe'r'f'its" antimicrobial action even after repeated washings. More particularly, the treatmehtdis' closed in these pending applications involves theinimersion of the material'in an'aqueous bath at hight'eni peratures, the bath includingas its principal ingredients a chelating agent, a catalyst'su-ch as sodium acetate an'd optionally a detergent along with'za suitable zincfcompound such as zinc chloride: A fixingagent rich in amine groups, such as urea, is applied'to thernaterial' either" in the'sarne bath' or in a second treatment solution to help lock the zinc in place on the fibers.
Although the treatment just described is satisfactory with respect to both the safety of operation and the quantity of zinc fixed in the fibers, there are nevertheless occasions when a more rapid mode of application is desirable. Thus, immersion of fabrics and the like for a prolonged period (e.g. 10 minutes) in a hot aqueous solution, followed by the necessary drying operation, represents a process which is practical only in industrial plants and can not be conveniently carried out in the home, in small institutions or in a store where an on-the-spot antimicrobial treatment of goods is desirable.
It is, therefore, an object of our present invention to provide an improved process for supplying such compositions to fibrous materials at ordinary temperatures and without the use of a slow-drying aqueous medium; a related object is to provide a modified antimicrobial composition adapted to be so applied.
In accordance with this invention we dissolve a zinc salt, a chelating agent, a catalyst, an aminating agent and preferably a detergent and buffering agent in an organic solvent, advantageously, a low-boiling ketone. When this mixture is applied, e.g. by spraying, to the material to be treated, it is found that the zinc compound reacts with the other ingredients to form a complex which remains fixed to the fiber over prolonged periods of use and exhibits distinct zones of inhibition against micro-organisms even after many washings in hot or cold water. It is further found that the use of low-boiling ketones is so effective in carrying the zinc into the fiber that a given percentage of zinc fixed in the fabric is obtainable with a greatly reduced proportion of zinc compound in the starting material, as compared with the hot-water treatment of the co-pending applications referred to above.
3,087,774 Patented Apr. 30, 1963 The following is a list" of ketones found suitable for the process'of our invention, the lower-boiling ones being preferred because of their shorter drying time.
TABLE 1 Compound: Boilingpo'int C.)
Trifluoro acetone-" 21 Acet s 56 Hexafluoroacetyl acetone; 63-65 Z-bntanone (ethyl methyl) B buten Z-one (methyl vinyl) 81 Biacetyl acetone 88 Methyl isopropyl ketone; 94.3 Diethyl acetone 1 02 Methyl propyl ketone 102.3 Pinacolone H V 106 Methyl isobutyl ketone 116.8 Cyclohexanone' 156' The folowing proportions (by weight) have been found to give a satisfactory mixture:
TABLE 2 p 7 Parts Zinccompound nn 5 to 500 Aminating agent- 5 to 300 Chelating agent l to Catalyst l'to 350 Detergent 0 to Buffering agent 0 to 200 Volatile organic solvent 1000 As an optional ingredient there may be added to the above mixture a commercially available moth-proofing agent soluble in the same solvent, such as from 1 to 50 parts of an alkali aluminum fluoride, or silico fluoride.
The zinc compound is preferably zinc chloride but may also be zinc sulphate or zinc nitrate.
Detergent such as ethylene cycloimido l-alkyl (fatty acid) 2-hydroxy ethylene sodium alcoholate methylene sodium carboxylate 10 17.5 grams of the above mixture together with 17.5 grams of urea crystals are dissolved in 1000 grams of acetone. The resulting solution is sprayed at room temperature by means of an atomizer onto a piece of cotton or wool textile and allowed to dry for about two minutes.
A sample of the textile so treated is washed 20 times in a household washing machine with soap or detergent and is then placed on a Petri dish containing agar streaked with a culture of Staphyl coccus aureus. After an incubation period of 24 hours a 2-mm. zone of inhibition is observed.
When the same mixture is sprayed on a piece of commercial air filter, a similar zone of inhibition is found to exist after 20 washings with a commercial detergent.
When a culture of Escherichia Coli is substituted for the Staphylococcus aureus, the zone of inhibition is found to be 3 mm.
3 Example 2 The same as Example 1, except that cyclohexanone is used as a solvent in place of acetone. The solution dries in about five minutes.
A l-mm. zone of inhibition against Staphylococcus aureus is observed after 20 washings.
Example 3 Methyl isobutyl ketone is used as a solvent in lieu of those given in Examples 1 and 2. The drying time is about three minutes. The same zone of inhibition is observed as in Example 2.
It may be mentioned that the concentration of the mixture of the aforedescribed solids in the organic solvent may vary from 0.1% to the saturation point, the latter being approximately 5%.
It should be noted that, especially with the addition of higher percentages of detergent or wetting agent, the composition according to the invention can also be used successfully on synthetic fibers, such as nylon.
Other alkali-metal acetates, such as potassium or 1ithium acetate, may be used as the catalyst in lieu of sodium acetate.
We claim:
1. An antimicrobial treating composition comprising a zinc salt, an aminating agent and a chelating agent all distributed in a volatile organic solvent.
2. A composition according to claim 1 wherein said volatile solvent is a ketone.
3. A composition according to claim 2 including as a catalyst an alkali-metal acetate.
4. A composition according to claim 3 including a detergent.
5. A composition according to claim 3 including a buffering agent.
6. As an article of manufacture, textile fiber impregnated with a composition comprising a zinc salt, an aminating agent and a chelating agent all distributed in a volatile organic solvent.
7. An article of manufacture according to claim 6 wherein the textile fiber is selected from the group consisting of cellulosic, proteinaceous and nylon fibers.
8. An antimicrobial treating composition comprising a zinc salt selected from the group consisting of zinc chloride, zinc sulfate and zinc nitrate; urea; sodium ethylenediamine-tetraacetate and a volatile organic solvent.
9. An antimicrobial treating composition according to claim 8 wherein said volatile organic solvent is a lowboiling ketone.
10. An antimicrobial treating composition according to claim 9 wherein said ketone is selected from the group consisting of acetone and methyl isobutyl ketone.
11. A process for imparting antimicrobial properties to textile fibers comprising applying to said fibers a solution of a zinc salt, an aminating agent and a chelating agent dissolved in a volatile organic solvent and allowing said solution to dry whereby antimicrobial properties are imparted to said textile fibers.
12. A process for imparting antimicrobial properties to textile fibers comprising applying to said fiber a solution of a Zinc salt, a chelating agent dissolved in a volatile organic solvent, treating the fiber with an aminating agent and allowing said fiber to dry whereby antimicrobial prop erties are imparted to said textile fiber.
References Cited in the file of this patent UNITED STATES PATENTS 2,304,478 Rosenzweig Dec. 8, 1942 2,396,514 Kreidl et al. Mar. 12, 1946 2,459,896 Schwarz Jan. 25, 1949 2,459,897 Schwarz Jan. 25, 1949 2,525,049 Signaigo Oct. 10, 1950 2,527,141 Mantell et al. Oct. 24, 1950 2,572,923 Gaver et al. Oct. 30, 1951 2,609,368 Gaver Sept. 2, 1952 2,671,779 Gaver et al. Mar. 9, 1954 2,785,106 Mendelsohn Mar. 12,, 1957 3,004,010 Mendelsohn Oct. 10, 1961

Claims (1)

11. A PROCESS FOR IMPARTING ANTIMICROBIAL PROPERTIES TO TEXTILE FIBERS COMPRISING APPLYING TO SAID FIBERS A SOLUTION OF A ZINC SALT, AND AMINATING AGENT AND A CHELATING AGENT DISSOLVED IN VOLATILE ORGANIC SOLVENT AND ALLOW ING SAID SOLUTION TO DRY WHEREIN ANTIMICROBIAL PROPERTIES ARE IMPARTED TO SAID TEXTILE FIBERS.
US845663A 1959-10-12 1959-10-12 Antimicrobial composition and process for applying same Expired - Lifetime US3087774A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US845663A US3087774A (en) 1959-10-12 1959-10-12 Antimicrobial composition and process for applying same
GB33990/60A GB920989A (en) 1959-10-12 1960-10-04 Improvements in or relating to treatment of fibres and the like to impart antimicrobial properties thereto
ES0261492A ES261492A1 (en) 1959-10-12 1960-10-05 Antimicrobial composition and process for applying same
CH1050362A CH368657A (en) 1959-10-12 1960-10-12 Process for imparting antimicrobial properties to made-up textile articles, and solution for implementing this process
ES0268776A ES268776A1 (en) 1959-10-12 1961-07-04 Antimicrobial composition and process for applying same

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2304478A (en) * 1939-10-19 1942-12-08 Rosenzweig Salo Process of treating materials comprising albumin, such as hair, bristles and the like
US2396514A (en) * 1943-03-20 1946-03-12 Ludwig Jekels Sterilizing materials and methods for making the same
US2459896A (en) * 1945-01-18 1949-01-25 Schwarz George Silver impregnation
US2459897A (en) * 1945-07-25 1949-01-25 Schwarz George Silver impregnation
US2525049A (en) * 1946-08-22 1950-10-10 Du Pont Cellulose titanate film production
US2527141A (en) * 1949-05-10 1950-10-24 United Merchants & Mfg Treatment of cotton fabrics with urea-alkali-zincate solution
US2572923A (en) * 1947-10-23 1951-10-30 Univ Ohio State Res Found Uniformly substituted glucopyranose polymers and process for their preparation
US2609368A (en) * 1950-10-21 1952-09-02 Univ Ohio State Res Found Carbohydrate processes
US2671779A (en) * 1948-06-08 1954-03-09 Univ Ohio State Res Found Carbohydrate products and processes therefor
US2785106A (en) * 1952-08-16 1957-03-12 Ions Exchange And Chemical Cor Process for making antiseptic article
US3004010A (en) * 1953-03-30 1961-10-10 Yardney International Corp High-polymer metal compounds and process for making same

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2304478A (en) * 1939-10-19 1942-12-08 Rosenzweig Salo Process of treating materials comprising albumin, such as hair, bristles and the like
US2396514A (en) * 1943-03-20 1946-03-12 Ludwig Jekels Sterilizing materials and methods for making the same
US2459896A (en) * 1945-01-18 1949-01-25 Schwarz George Silver impregnation
US2459897A (en) * 1945-07-25 1949-01-25 Schwarz George Silver impregnation
US2525049A (en) * 1946-08-22 1950-10-10 Du Pont Cellulose titanate film production
US2572923A (en) * 1947-10-23 1951-10-30 Univ Ohio State Res Found Uniformly substituted glucopyranose polymers and process for their preparation
US2671779A (en) * 1948-06-08 1954-03-09 Univ Ohio State Res Found Carbohydrate products and processes therefor
US2527141A (en) * 1949-05-10 1950-10-24 United Merchants & Mfg Treatment of cotton fabrics with urea-alkali-zincate solution
US2609368A (en) * 1950-10-21 1952-09-02 Univ Ohio State Res Found Carbohydrate processes
US2785106A (en) * 1952-08-16 1957-03-12 Ions Exchange And Chemical Cor Process for making antiseptic article
US3004010A (en) * 1953-03-30 1961-10-10 Yardney International Corp High-polymer metal compounds and process for making same

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Publication number Publication date
GB920989A (en) 1963-03-13
ES261492A1 (en) 1961-10-01
ES268776A1 (en) 1961-12-01
CH368657A (en) 1963-04-15

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