WO2021100044A1 - Procédés de fusion d'hôtes cyclodextrines avec une finition non-tissée pour former des tissés intelligents contenant divers agents bénéfiques et produits fabriqués à partir des procédés - Google Patents

Procédés de fusion d'hôtes cyclodextrines avec une finition non-tissée pour former des tissés intelligents contenant divers agents bénéfiques et produits fabriqués à partir des procédés Download PDF

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Publication number
WO2021100044A1
WO2021100044A1 PCT/IL2020/051199 IL2020051199W WO2021100044A1 WO 2021100044 A1 WO2021100044 A1 WO 2021100044A1 IL 2020051199 W IL2020051199 W IL 2020051199W WO 2021100044 A1 WO2021100044 A1 WO 2021100044A1
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WO
WIPO (PCT)
Prior art keywords
active
finishing
cyclodextrin
filamentous material
solution
Prior art date
Application number
PCT/IL2020/051199
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English (en)
Inventor
Elena POVERENOV
Miryam KLEIN
Stella Kiel
Ariel Yedvab
Original Assignee
Avgol Ltd.
The State Of Israel, Ministry Of Agriculture & Rural Development, Agricultural Research Organization
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 Avgol Ltd., The State Of Israel, Ministry Of Agriculture & Rural Development, Agricultural Research Organization filed Critical Avgol Ltd.
Publication of WO2021100044A1 publication Critical patent/WO2021100044A1/fr

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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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/16—Cyclodextrin; Derivatives thereof
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof

Definitions

  • the present invention relates generally to methods of finishing filamentous material, such as nonwoven fabrics, and the products made with such methods.
  • the host molecule b-cyclodextrin (b-CD) that belongs to a family of cyclodextrins is a cyclic oligosaccharide with a truncated cone structure which is regulatory safe and utilized in food, medicine, and cosmetics.
  • the hydrophobic inner cavity of the b-CD could allow for a complex creation with different active agents.
  • a hydrophilic active agent can also interact with b-CD by hydrogen interactions to form a complexation. In specific conditions, these interactions can be broken, and the active agent can be released.
  • a method is disclosed to finish a filamentous material (e.g., nonwoven fabric) that differs from the literature cited herein.
  • the method includes the linkage of unmodified b-CD to the surface of an unmodified fabric utilizing the typical commercially available hydrophilic finishing formulations (e.g., silastol) that are regularly used in the nonwoven industry.
  • the inventive method is compatible with the existing equipment and factory lines in the nonwoven industry.
  • the reaction of the method can be carried out in water without appreciable organic solvents or adding extrinsic agents.
  • the approach allows the use of a high variety of active agents which could be loaded into the filamentous material and controllably released.
  • the inventors of the present invention have named this approach "the bucket concept".
  • the active finishing utilized in the present invention that contains b-CD bucket, allows the incorporation of otherwise incompatible active agents (for instance hydrophobic agents) with nonwoven fabrics, to protect sensitive active agents that have a tendency for fast decomposition, to encapsulate volatile active agents to prevent their escape from the fabric surface, and, in general, to increase the capacity of the fabrics toward active agents.
  • the bucket concept allows prolonged controlled release of the active agents that can be regulated by temperature, humidity, or pH.
  • Active agents that can be used for the purposes of the present invention include, but are not limited to, hydrophilic agents, hydrophobic agents, and more specifically, curcumin, thymol and linoleic acid.
  • a method of finishing a filamentous material includes the steps of: providing a filamentous material; providing an active finishing mixture comprising a cyclodextrin and at least one active agent; and applying the active finishing mixture to the filamentous material.
  • the methods of the present invention do not utilize fabric surface activation and/or auxiliary linkers and/or organic solvents.
  • the cyclodextrin is one or more of: an unmodified a-cyciodextrin; an unmodified b-cyclodextrin; or an unmodified g-cyc!odextrin.
  • the filamentous material is a non-woven fabric.
  • the step of applying the finishing mixture comprises one or more of the following: coating the filamentous material with the active finishing mixture; immersing the filamentous material in the active finishing mixture; or printing the active finishing mixture on the filamentous material.
  • the active agent is curcumin or iinoleic acid.
  • the method further includes the steps of: preparing a first solution comprising water, b-cyclodextrin, and a finishing formulation; preparing a second solution comprising said at least one active agent; and mixing said first and second solutions to produce said active finishing mixture.
  • neither the first nor the second solutions comprise organic solvents or auxiliary linkers.
  • the step of preparing the first solution further comprises maintaining a concentration of the b-cyciodextrin of about 0.4 mM and maintaining a concentration of the finishing formulation between about 0.005% and about 0.8% (w/v).
  • the step of mixing the first and second solutions includes stirring the first and second solutions for about 24 hours at an ambient or room temperature of between about 15° C and about 25° C.
  • the step of preparing the second solution comprises combining the active agent in the form of curcumin with ethanol.
  • the method further includes the sequential steps of: preparing a first solution comprising distilled water and b- cyciodextrin at a concentration of about 0.4 mM; adding said active agent in the form of linoleic acid to said first solution; mixing said first solution; adding a finishing formulation to said first solution; and then mixing said first solution to form said active finishing mixture.
  • a filamentous material in another broad form of the present invention, includes a nonwoven fabric substrate and an active finishing mixture applied to the nonwoven fabric substrate.
  • the active finishing mixture includes a cyclodextrin and at least one active agent.
  • the cyclodextrin is an unmodified b-cyclodextrin.
  • the at least one active agent is linoleic acid or curcumin.
  • Fig. 1 is a schematic illustration of a filamentous material substrate with an active finishing according to the present invention wherein the finishing includes b-CD with active agents;
  • Fig. 2A is a graph showing attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectra that shows the incorporation of curcumin on Avgol nonwoven materials using the bucket concept of the present invention
  • Fig. 2B is a graph showing attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectra that show the incorporation of thymol on Avgol nonwoven materials using the bucket concept of the present invention
  • Fig. 3A shows a bar chart comparing the amount of a curcumin loaded active agent in various filamentous materials prepared with the inventive method compared to filamentous material controls;
  • Fig. 3B shows a bar chart comparing the amount of a thymol loaded active agent in various filamentous materials prepared with the inventive method compared to filamentous material controls;
  • Fig. 4 shows a bar chart comparing the activity (IL-1 a) of a filamentous material (100% viscose nonwoven fabric) loaded with an active agent (curcumin) prepared according to the inventive method to a control;
  • Fig. 5A shows a graph of the release rate of a curcumin active agent from of a filamentous material prepared according to the inventive method in a 10% EtOFI solution at 25 s C;
  • Fig. 5B shows a graph of the release rate of a curcumin active agent from of a filamentous material prepared according to the inventive method in a pH 7 solution at 37 s C;
  • Fig. 5C shows a graph of the release rate of a curcumin active agent from of a filamentous material prepared according to the inventive method in a pH 4.5 solution at 37 s C;
  • Fig. 6 is a photograph showing an active finishing mixture according to the present invention, the active finishing mixture comprising b-CD, curcumin as an active agent, ethanol, water, and a finishing formulation of silastol 163;
  • Fig. 7A shows a photograph of a first exemplary coating means used in the active finishing method according to the present invention, and Fig. 7A shows a kiss-roll means of coating a filamentous material with the active finishing;
  • Fig. 7B shows a photograph of a second exemplary coating means used in the active finishing method according to the present invention, and Fig. 7B shows a dip-coating means of coating a filamentous material with the active finishing;
  • Fig. 8 shows a bar chart comparing the biological activity (MTT) of a filamentous material loaded with an active agent (curcumin) prepared according to the inventive method to a control;
  • Fig. 9A shows a bar chart comparing the biological activity (MTT) of a filamentous material loaded with various active agents prepared according to the inventive method.
  • Fig. 9B shows a bar chart comparing the therapeutic effect activity (IL-1 a) of a filamentous material loaded with various active agents prepared according to the inventive method.
  • Filamentous material may be a woven, nonwoven, film or other disposable polymer construct.
  • Suitable polymeric materials include thermal melt and thermoset polymers, with thermal melt plastics being particularly preferred.
  • Thermal melt plastics include polyolefins, and more preferably polypropylene or polyethylene.
  • Other polymers suitable for use include polyesters, such as polyethylene terephthalate; polyamides; polyacrylates; polystyrenes; thermoplastic elastomers, block polymers, polymer alloys; and blends of these and other known fiber forming thermoplastic materials.
  • Useful embodiments of products including the active finishing according to the present invention may include such things as: “SMS” or spunbond-meltblown- spunbond nonwoven fabrics wherein a first spunbond layer comprises an antimicrobial agent, a second spunbond layer comprises an antimicrobial inactivation agent, and a meltblown material creates a spatial separation between the first and second spunbond layers.
  • SMS spunbond-meltblown- spunbond nonwoven fabrics wherein a first spunbond layer comprises an antimicrobial agent, a second spunbond layer comprises an antimicrobial inactivation agent, and a meltblown material creates a spatial separation between the first and second spunbond layers.
  • Such an embodiments can include variations in the number, composition, construction and basis weight of layers of spunbond and/or meltblown as well as inclusion of one or more components comprising manmade or natural finite length fibers such as absorbents including cellulosics and superabsorbent beads, particles or fibers.
  • Useful embodiments of products including the active finishing according to the present invention may include such things as: feminine pads comprising one or more antimicrobial agents with antimicrobial inactivation disposable envelopes; antimicrobial component adult incontinence diapers with antimicrobial inactivation; individual or bulk disposal bags; and antimicrobial bandaging with antimicrobial inactivation wrap.
  • Typical nonwoven fabrics made from certain polymers, such as polypropylene, are hydrophobic.
  • a finishing formulation or surface treatments to impart hydrophilic properties to the nonwoven fabric substrate to achieve performance in liquid strike-through and liquid runoff that is required for their use in absorbent products.
  • Suitable finishing treatments are proprietary blends of synthetic surfactant solutions which are commercially available, for example, from Schill + Seilacher AG (e.g. Silastol PHP 26, Silastol PHP 90, & Silastol 163), and Pulcra Chemicals (e.g. Stantex S 6327, Stantex S 6087-4, & Stantex PP 602).
  • Figure 1 shows a schematic illustration of a method according to the present invention, whereby a filamentous material substrate is treated with an active finishing comprising b-CD with effective encapsulation of an active agent or agents.
  • the present invention involves the linkage of unmodified b-CD to the unmodified fabric's surface.
  • the active finishing utilizes finishing formulations (e.g., Silastol 163, or other commercially available finishing formulations) that are regularly used in the nonwoven industry and compatible with the existing equipment and factory lines.
  • the active finishing reaction is advantageously carried out in water without organic solvents or adding extrinsic agents, and may be applied by conventional or special means such as spraying, dipping or immersing, contact, printing, or other application methods.
  • the preferred active finishing method of the present invention utilizes b-CD as a bucket to allow the incorporation of otherwise active agents that are incompatible with non-woven fabrics (for instance hydrophobic agents), to protect sensitive active agents that have a tendency of fast decomposition, to encapsulate volatile active agents and prevent their escape from the fabric surface, and, in general, to increase the capacity of the fabrics toward active agents.
  • the bucket concept allows prolonged controlled release of the active agents that can be regulated by temperature, humidity, or pH ( Figure 1).
  • the synthetic procedure for preparation of b-CD/curcumin/finishing formulation and application on nonwovens includes the following steps: i) providing 1 L of an active finishing solution comprising of b-CD, curcumin, and finishing formulation, two solutions were prepared: 1. to 868 ml distilled water 170 ml of the finishing formulation (0.8%w/v) and 4 g of b-CD were added, then the mixture was stirred at ambient temperature to homogeneity; 2. add 1 .3 g of curcumin to 130 ml of ethanol, the mixture was stirred at ambient temperature to homogeneity. Then mixture 2 was added to the mixture 1 and the obtained mixture was eventually stirred at ambient temperature for 24 hrs. ii) applying the obtained final mixture to nonwoven fabrics by coating/printing/ dip coating.
  • the synthetic procedure for preparation of b-CD/linoleic acid/finishing formulation and application on nonwovens includes the following steps: i) providing 107 ml of an active finishing solution comprising of b-CD, linoleic acid, and finishing formulation, 0.45 g of b-CD (0.4 mM) was dissolved in 100 ml of distilled water. To this solution, 6 ml linoleic acid was added, and the mixture was stirred for 30 min to allow the inclusion of linoleic acid into b-CD molecules. Then 1 ml of the finishing formulation was added to the mixture and it allowed to stir at ambient temperature for 24 hrs. ii) applying the obtained final mixture to nonwoven fabrics by coating/printing/ dip-coating.
  • a general synthetic procedure for preparation of b-CD/active agent/finishing formulation and application on nonwovens includes the following steps: i) providing an active finishing solution comprising of b-CD, an active agent, and finishing formulation, two solutions must be prepared: 1. an aqueous solution of b-CD and finishing formulation, keeping the b-CD concentration about 0.4 mMol and the finishing formulation concentration ranging from 0.005 up to 0.8% (w/v). Then an active agent/an active agent solution should be added to the above mixture and the received mixture must be kept stirred at ambient temperature for 24 hrs. ii) applying the obtained final mixture to nonwoven fabrics by coating/printing/dip coating.
  • hydrophobic molecules will have a higher probability to enter the b-CD in an aqueous solution than hydrophilic molecules of the same size.
  • another cyclodextrin molecule can be selected depending on the characteristics of the active agent molecule, such as a-CD for smaller molecules, and g-CD for larger molecules.
  • Nonwoven polypropylene fabrics manufactured by Avgol Ltd. were used to prepare smart nonwovens with the bucket concept.
  • an active finishing solution was prepared by linkage of b-CD to a commercial finishing formulation (according to the protocols of paragraphs [0039] and [0040] detailed above), followed by a deposition of the prepared solution using spreading on the nonwoven surface.
  • the incorporation of active agents was confirmed by FTIR-ATR. In this case, the active agents selected were curcumin and thymol.
  • the release study demonstrated a link between the release rate of curcumin and environmental factors such as temperature and pH. It was found that the release rate decreases in acidic pH and with the temperature elevation. The decrease in the release rate in an acidic pH can be explained by the positive charge of curcumin molecules at this pH. Thus, the inventors have found that the affinity of curcumin to b-CD molecules at the acidic pH increases due to hydroxylic groups.
  • a pilot experiment was performed at Avgol Ltd. For this experiment, 30 L of a solution comprised of b-CD, curcumin, ethanol, water, and a finishing formulation (Silastol 163) was prepared.
  • the fabric used was 13 gsm Spunbond, Hydrophobic.
  • the pilot experiment was done using two coating methods: coating by the kiss-roll method and by dip-coating method.
  • the coating was applied to a fabric which “kisses” the surface of a coating roll.
  • Figure 7A In the second method, a fabric was immersed in the coating solution.
  • Figure 7B In the second method, a fabric was immersed in the coating solution.
  • DPG dipotassium glycyrrhizinate
  • vitamin B3 niacinamide
  • linoleic acid linoleic acid
  • Preparing a composition, useful to coat e.g. textile materials, shoes, diapers, airplanes and plastics comprises dispersing a gel- forming materia! in an aqueous soiution and adding cyciodextrin derivative to the dispersion.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention concerne un procédé de finition d'un matériau filamenteux comprenant l'application d'un mélange de finition active à un matériau filamenteux. Le mélange de finition active comprend une cyclodextrine et au moins un agent actif. Le procédé utilise la finition qui est régulièrement utilisée dans l'industrie des textiles non-tissés et est compatible avec l'équipement existant et les lignes d'usine existantes. La finition active comprend préférablement de la β-cyclodextrine qui permet l'incorporation d'agents actifs sensibles autrement incompatibles (par exemple des agents hydrophobes), pour protéger les agents actifs sensibles qui ont une tendance à la décomposition rapide, pour encapsuler des agents actifs volatils et empêcher leur fuite de la surface de textile et, en général, pour accroître la capacité des textiles vis-à-vis des agents actifs.
PCT/IL2020/051199 2019-11-20 2020-11-19 Procédés de fusion d'hôtes cyclodextrines avec une finition non-tissée pour former des tissés intelligents contenant divers agents bénéfiques et produits fabriqués à partir des procédés WO2021100044A1 (fr)

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US201962938140P 2019-11-20 2019-11-20
US62/938,140 2019-11-20

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WO2021100044A1 true WO2021100044A1 (fr) 2021-05-27

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