EP3994305A1 - Colorants antimicrobiens pour vêtements de soins de santé - Google Patents

Colorants antimicrobiens pour vêtements de soins de santé

Info

Publication number
EP3994305A1
EP3994305A1 EP20734586.9A EP20734586A EP3994305A1 EP 3994305 A1 EP3994305 A1 EP 3994305A1 EP 20734586 A EP20734586 A EP 20734586A EP 3994305 A1 EP3994305 A1 EP 3994305A1
Authority
EP
European Patent Office
Prior art keywords
phthalocyanine
healthcare
healthcare apparel
fabric
apparel according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP20734586.9A
Other languages
German (de)
English (en)
Inventor
Mark Wilkinson
Paul Wight
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BMG British Medical Group Ltd
Original Assignee
Chemical Intelligence Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chemical Intelligence Ltd filed Critical Chemical Intelligence Ltd
Publication of EP3994305A1 publication Critical patent/EP3994305A1/fr
Pending legal-status Critical Current

Links

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
    • A—HUMAN NECESSITIES
    • A41—WEARING APPAREL
    • A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
    • A41D31/00—Materials specially adapted for outerwear
    • A41D31/04—Materials specially adapted for outerwear characterised by special function or use
    • A41D31/30—Antimicrobial, e.g. antibacterial
    • A—HUMAN NECESSITIES
    • A41—WEARING APPAREL
    • A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
    • A41D13/00—Professional, industrial or sporting protective garments, e.g. surgeons' gowns or garments protecting against blows or punches
    • A41D13/12—Surgeons' or patients' gowns or dresses
    • 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
    • D06P1/14—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 phthalocyanine dyes without vatting

Definitions

  • the present invention relates to an antimicrobial fabric for healthcare apparel, healthcare apparel comprising said antimicrobial fabric, and a process for treating a fabric suitable for healthcare apparel.
  • HAI Hospital Acquired Infections
  • Gowns are typically made up of multiple layers. These layers can be made from a variety of materials such as polyethylene, polypropylene, polyester or polyurethane. Gowns may be used by patients or healthcare workers. The duration of wear may be very short (minutes), or may be multiple hours - for example in a surgical setting. Such gowns provide a basic level of protection by acting as a simple barrier to pathogens, but unless bacterial and viruses are rapidly killed they may grow and become a contaminating source.
  • WO2010/118180 claims the chemical attachment of photosensitising dyes to fabrics for odor control.
  • W093/00815 discusses dyeing of polymers with photosensitising phthalocyanines, but not cationic dyes.
  • JP2005023473 details a robe or gown for medical applications, made from functionalised synthetic fibres coated with typical conventional biocides. It gives an example of quaternary ammonium salts, but claims a wide variety of biocides. It does not claim photosensitisers or activity mediated by singlet oxygen.
  • JP3247293 (1995) reports cellulose acetate fibres with antimicrobial properties given by metals salts such as silver or zinc.
  • CN201109221 claims an antimicrobial water resistant fabric for disposable hospital wear. It makes no claims for the antimicrobial action being mediated by photosensitisers.
  • the antimicrobial additive is silver.
  • KR20140104256 teaches a manufacturing method for an antimicrobial fabric suitable for gowns.
  • a biocide is included in the manufacturing method, but not specifically claimed in the patent.
  • the fabric is made from polyurethane / polylactic acid with zinc and bamboo cellulose incorporated to gift antimicrobial activity.
  • US2018066384 teaches that treatment of any natural or synthetic fibre with a formulated copper sulfide solution produces antimicrobial fibres claimed suitable for industrial, military and healthcare clothing, including gowns.
  • CN108914610 (2018) specifically claims a disposable hospital gown.
  • the added biocide is claimed to be a quaternary ammonium salt or metal ion.
  • CN105839410 (2016) details a surgical gown produced from zinc oxide, woven with silver wire and coated with PHMB.
  • US20090081911 details a surgical gown with an outer layer of spunbond polypropylene. This polypropylene layer is stated to have antibacterial properties, potential by acting as a barrier. No additional biocides are claimed.
  • the present invention identifies certain dyes that are suitable for depositing on fibres that may be used in healthcare apparel, and demonstrates their antimicrobial properties.
  • the present invention provides an antimicrobial fabric for healthcare apparel comprising a singlet oxygen generating photosensitising dye.
  • the present invention further provides a process for treating a fabric suitable for healthcare apparel with a singlet oxygen generating phthalocyanine.
  • the present invention identifies certain dyes which are suitable for depositing on fibres (for example polyethylene, polypropylene, polyester, nylon, cellulose or polyurethane) that may be used to construct healthcare apparel, and demonstrates their antimicrobial properties.
  • the healthcare apparel can be any of patient gowns, health worker gowns, surgical gowns, all over hazmat (hazardous material) suits, uniforms or scrubs.
  • the dye of the present invention is cationic or anionic.
  • Cationic dyes are preferred and have been found to have an unexpected affinity for fabrics (e.g. cellulose, polyester, nylon), enabling their efficient deposition without chemical attachment, and additionally sufficient water solubility to enable dyeing.
  • the antimicrobial fabric or material may comprise at least one layer of nonwoven fabric, for example meltblown or spunbond formed polypropylene, polyethylene, polyester, cellulose or nylon, onto which is deposited a singlet oxygen generating photosensitising dye.
  • the facemask comprises or consists of a non-woven fabric.
  • the fabric or material of the apparel may incorporate the singlet oxygen generating photosensitising dye.“Incorporate” may include the concepts of coated, impregnated or dyed.
  • the fabric or material is comprised of multiple layers, which may or may not be identical.
  • the present invention relates to the application of certain photosensitisers as generators of singlet oxygen, a method for their application to materials suitable for healthcare apparel, and an antimicrobial gown obtainable using the invention.
  • Dyes may be selected from structural classes such as phthalocyanines, porphyrins, dipyrrole-boron complexes (BODIPY), phenothiazines (e.g. Methylene Blue) and fluoresceins (e.g. Rose Bengal).
  • structural classes such as phthalocyanines, porphyrins, dipyrrole-boron complexes (BODIPY), phenothiazines (e.g. Methylene Blue) and fluoresceins (e.g. Rose Bengal).
  • Singlet oxygen generators are known to destroy microorganisms.
  • Singlet oxygen has a greater energy than ground-state, triplet oxygen.
  • the singlet and triplet states of oxygen are distinguished by the singlet state having two electrons of anti-parallel spins and the triplet state having an uncoupled pair of electrons with parallel spins.
  • Singlet oxygen is also distinguished from triplet oxygen because it is a highly reactive species with a lifetime from a few microseconds to several hundred microseconds. During its lifetime singlet oxygen has the potential to react before being deactivated, and therefore has a wide number of applications, including antimicrobial applications such as in medical gloves, facemasks, gowns and other healthcare apparel.
  • Preferred singlet oxygen generating dyes according to the present invention are phthalocyanines.
  • the phthalocyanine is alpha substituted.
  • phenothiazine class of dyes for example Methylene Blue.
  • the phthalocyanine nucleus may be aluminium, titanium or zinc. If aluminium or titanium is used, the metal may be further substituted by alkyl, aryl, alkoxy, hydroxy or halogen. Aluminium, titanium and zinc are chosen because they are more efficient in generating singlet oxygen than other metals such as copper or nickel, and they are reasonably small and so can be inserted into the phthalocyanine easily, with the reactions occurring under air, in good yield, as opposed to other metals such as using SiCU, and are easily available in bulk.
  • the central metal atom also influences the position of the absorption maximum of the phthalocyanine. Zinc, titanium and aluminium are preferred in the compounds because their absorption is in the visible region of the spectrum especially between 600 - 700 nm. The zinc compounds described herein are especially preferred.
  • each of the pendant organic radicals linked to the phthalocyanine nucleus may be any aromatic or heteroaromatic moiety. Any one phthalocyanine nucleus may carry two or more different organic radicals. This radical may be linked to the phthalocyanine core by a carbon or hetero-atom bridge. Examples include, but are not limited to oxygen linked phenyl, pyridyl and N-alkylated pyridinium, Examples of N-alkylated pyri dines are 3- hydroxy-1 -methylpyri din-1 -ium, 3-hydroxy-l-ethylpyridin-l-ium, 3-hydroxy-l-propylpyridin-l-ium.
  • the phthalocyanines used in the present invention preferably have substituents to the phthalocyanine nucleus in the alpha position, adjacent to the phthalocyanine nucleus. This alpha substitution decreases aggregation of the phthalocyanine. Aggregation is known to reduce singlet oxygen generation efficiency, and therefore this structure prevents aggregation and increases efficiency singlet oxygen generation and hence antimicrobial and other activity.
  • the molecules described herein have other desirable properties. They are more thermally stable, and stable to radical degradation than commercially available analogs such as Tinolux BBS and Tinolux BMC.
  • the phthalocyanine according to the present invention has a structure with the following formula:
  • M is selected from aluminium, titanium or zinc
  • R R’(a) or R”(b)
  • R’ Oxygen linked phenyl or pyridyl
  • X C , Br , G, methanesulphonate, ethanesulphonate, toluenesulfonate, formate, acetate or other inorganic or organic counter-ion or mixture thereof; and wherein alkylation on the pyridine nitrogen is optionally branched C1-C8 alkyl. This alkyl chain may be further hydroxylated or fluorinated.
  • the phthalocyanines used in the present invention are activated by light and offer a sustained release of singlet oxygen onto the gown or other apparel. It is known that singlet oxygen is a strong antimicrobial agent, killing most bacteria.
  • the advantage of singlet oxygen generating dyes is that they are catalytic and not exhausted over time, and the singlet oxygen they release is not persistent, due it its very short half-life of typically a few microseconds. This has major advantages in toxicity and potential for development of resistant organisms. The short lifetime and hence short diffusion range of singlet oxygen gives this invention a significant advantage in safety for users.
  • the phthalocyanines preferred in the present invention have substituents to the phthalocyanine nucleus in the alpha position, adjacent to the phthalocyanine nucleus (positions 1,5, 12 and 13 in Formula 1). This alpha substitution decreases aggregation of the phthalocyanine. Aggregation is known to reduce singlet oxygen generation efficiency, and therefore this structure prevents aggregation and increases efficiency singlet oxygen generation and hence antimicrobial and other activity.
  • phthalocyanine I was compared to an analogue where the oxypyridinium residue was attached to the phthalocyanine core in the beta position (positions 3,6,11 and 14 in Formula 1). 25 mgs of each were dissolved in 1 L water, and the UV / vis absorption compared.
  • the phthalocyanines of Formula 1 can be prepared by reacting:
  • the alkylation of the pyridine groups is done last. If the alkylation process is not done to completion, some of the pyridyl substituents can remain unalkylated and uncharged. The process can be modified by temperature and stoichiometry to give higher or lower degrees of final alkylation.
  • the antimicrobial phthalocyanines illustrated in present invention can be used to coat fibres suitable for gown manufacture and can provide effective and continuous antimicrobial protection. In addition, the physical properties of the gown are not significantly reduced.
  • the phthalocyanines used can be applied to any material suitable for gown or healthcare apparel construction. Examples are, but not limited to polyester, polypropylene, polyester or polyurethane.
  • the application of the phthalocyanines to the fibres may be achieved via a wide variety of methods familiar to those skilled in the art of textile dyeing. Examples may include, but are not limited to -
  • a particular advantage of the pthalocyanines preferred in this invention is their high solubility in selected solvents which allow facile dyeing of the desired fibres.
  • the present inventors have realised that application of the photosensitising phthalocyanines as solutions is a particular advantage of the invention as it maintains the phthalocyanine in a de-aggregated state (in contrast to slurries, suspensions or dispersions). Aggregation is known to decrease the generation of singlet oxygen by photosensitisers. As such, the photosensitiser may be applied at a low weight loading per square meter of fabric, whilst still giving high antimicrobial activity.
  • a homo or heteropolymer of unsaturated low molecular weight carboxylic acids may also be deposited onto facemask material, such as the non-woven fabric.
  • Example monomers include acrylic, methacrylic or maleic acids
  • example polymers include the carbomer class, such as acrylic acid homopolymers, or maleic acid / vinyl ether heteropolymers.
  • the carboxylic acid polymer is deposited on the same fabric layer as the photosensitiser, being the outer layer of the apparel.
  • the homo or heteropolymer may be deposited on the fabric first, enabling deposition of the dye without chemical attachment.
  • a surfactant may also be included.
  • the surfactant is an ionic, or alternatively a betaine type surfactant.
  • Preferred is an ionic sulfonated aryl surfactant, such as an alkylbenzene sulfonate, preferably sodium dodecylbenzenesulfonate.
  • the reaction mixture is transferred to the second vessel to precipitate the crude product, which is isolated by filtration and washed with further iso-propanol.
  • the wet cake of the crude product is recharged to a vessel with iso-propanol (8 vols, 1 100 mL) and lithium iodide trihydrate (35 g, 0.187 mol, 1.27 eq).
  • the slurry is heated to 80 - 83 °C (internal), then cooled to room temperature.
  • the final product is isolated by filtration and washed with further iso-propanol, before being dried in an oven.
  • the wet cake is recharged to a vessel with iso-propanol (150 ml) and sodium iodide (1 g, 0.0067 mol, 1.27 eq). Water (15 ml) is added, and the slurry heated to 40 °C for 3 h, then cooled to room temperature and further stirred. The product is isolated by filtration, then washed with iso-propanol / water, then finally washed with further iso-propanol before being dried in an oven.
  • Example 6 Dyeing fabric with solution of Example 2 in methanol
  • Example 2 0.025 g of the phthalocyanine prepared in Example 2 was dissolved in 100 ml of methanol. A 10 x 10 cm square of polypropylene fabric (suitable for gown construction) was immersed in the solution for 15 seconds with swirling. The sample was carefully removed from the liquid, allowing the excess to run off. The sample was air dried.
  • Example 7 Dyeing fabric with solution of Example 2 in methanol
  • Example 2 0.025 g of the phthalocyanine prepared in Example 2 was dissolved in 100 ml of methanol. A 10 x 10 cm square of polyethylene fabric (suitable for gown construction) was immersed in the solution for 15 seconds with swirling. The sample was carefully removed from the liquid, allowing the excess to run off. The sample was air dried.
  • Example 8 Dyeing fabric with solution of Example 3 in acetone
  • Example 3 0.025 g of the phthalocyanine prepared in Example 3 was dissolved in 1 ml NMP and made up to 100 ml with acetone. A 10 x 10 cm square of polypropylene fabric (suitable for gown construction) was immersed in the solution for 15 seconds with swirling. The sample was carefully removed from the liquid, allowing the excess to run off. The sample was air dried.
  • Example 9 Dyeing fabric with solution of Example 5 in acetone
  • Example 5 0.025 g of the phthalocyanine prepared in Example 5 was dissolved in 100 ml of acetone. A 10 x 10 cm square of polypropylene fabric (suitable for mask construction) was immersed in the solution for 15 seconds with swirling. The sample was carefully removed from the liquid, allowing the excess to run off. The sample was air dried.
  • Example 10 Dyeing fabric with Carbomer, then solution of Example 2 in water
  • An 8.7 cm diameter disc of a polyethylene / polyester laminate fabric (suitable for a gown, apron or “hazmat” suit) was treated with a suspension of 150 mgs of an acrylic acid homopolymer (for example Carbopol 971) and 75 mgs of sodium dodecylbenzenesulfonate in 50 g water.
  • the disc was treated for 1 min, then the sample was carefully removed from the liquid, allowing the excess to run off.
  • the sample was air dried.
  • 0.025 g of the phthalocyanine prepared in Example 2 was dissolved in 100 ml of water. 2.5 g of this solution was made up to 15 g.
  • the disc prepared above was treated with 4 g of this dye solution for 1 min, then the sample was carefully removed from the liquid, allowing the excess to run off. The sample was air dried.
  • Example 11 Dyeing of fabric with Carbomer and Dye of Example 2 in water
  • 0.025 g of the phthalocyanine prepared in Example 2 was dissolved in 100 ml of water. To 75 ml of this solution was added 150 mgs of an acrylic acid homopolymer (for example Carbopol 971) and 75 mgs of sodium dodecylbenzenesulfonate. The suspension was stirred until fully dispersed. An 18 cm square of non-woven polypropylene fabric was dipped in this suspension for 2 min, then the sample was carefully removed from the liquid, allowing the excess to run off. The sample was air dried.
  • an acrylic acid homopolymer for example Carbopol 971
  • sodium dodecylbenzenesulfonate 75 mgs of sodium dodecylbenzenesulfonate
  • a 4.3 cm disc of the sample prepared in Example 6 was inoculated with a 0.1 ml presentation of either Staphylococcus aureus or Klebsiella pneumonia. After lh at 37 °C under illumination of 1500 lux, a reduction of 5.5 Log was achieved for Staph a and 2.1 Log for Kleb p.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un tissu antimicrobien pour vêtement de soins de santé comprenant un colorant photosensibilisant générant de l'oxygène singulet, de préférence, le colorant étant une phtalocyanine cationique.
EP20734586.9A 2019-07-01 2020-07-01 Colorants antimicrobiens pour vêtements de soins de santé Pending EP3994305A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP19183704 2019-07-01
PCT/EP2020/068562 WO2021001445A1 (fr) 2019-07-01 2020-07-01 Colorants antimicrobiens pour vêtements de soins de santé

Publications (1)

Publication Number Publication Date
EP3994305A1 true EP3994305A1 (fr) 2022-05-11

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EP20734586.9A Pending EP3994305A1 (fr) 2019-07-01 2020-07-01 Colorants antimicrobiens pour vêtements de soins de santé

Country Status (5)

Country Link
US (1) US20220386724A1 (fr)
EP (1) EP3994305A1 (fr)
CN (1) CN114555881A (fr)
CA (1) CA3145595A1 (fr)
WO (1) WO2021001445A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3553062A1 (fr) 2018-04-09 2019-10-16 Chemical Intelligence Limited Composés antimicrobiens et agents anticancéreux a base de phthalocyanines cationiques
EP3994216A1 (fr) 2019-07-01 2022-05-11 Chemical Intelligence Limited Colorants antimicrobiens pour masques faciaux
US12049095B2 (en) 2019-07-01 2024-07-30 Bmg (British Medical Group) Limited Antimicrobial medical glove printing method
WO2021207268A1 (fr) * 2020-04-07 2021-10-14 Abc Filtration Corp. Papr amélioré avec revêtements résistants aux virus
EP3933102A1 (fr) * 2020-06-29 2022-01-05 Ortner Cleanroom Engineering GmbH Nappe textile, vêtement, son procédé de fabrication, fonctionnalisation d'une nappe textile et l'utilisation d'un photosensibilisateur fixé à la surface d'une nappe textile
US11458220B2 (en) 2020-11-12 2022-10-04 Singletto Inc. Microbial disinfection for personal protection equipment
CN113787786B (zh) * 2021-08-09 2022-05-20 江南大学 一种夜光储能长效光动力抗菌型面料及其制备方法
US12359369B2 (en) 2022-08-11 2025-07-15 Singletto Inc. Skin protection against microbial particles
KR20240150191A (ko) * 2023-04-07 2024-10-15 삼성전자주식회사 조성물 및 이의 제조 방법

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Also Published As

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WO2021001445A1 (fr) 2021-01-07
US20220386724A1 (en) 2022-12-08
CA3145595A1 (fr) 2021-01-07
CN114555881A (zh) 2022-05-27

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