[go: up one dir, main page]

WO2024181924A1 - Compositions comprenant du chlorure d'acide gras, de l'anhydride alcényle succinique et/ou un dimère d'alkyle-cétène - Google Patents

Compositions comprenant du chlorure d'acide gras, de l'anhydride alcényle succinique et/ou un dimère d'alkyle-cétène Download PDF

Info

Publication number
WO2024181924A1
WO2024181924A1 PCT/SG2024/050114 SG2024050114W WO2024181924A1 WO 2024181924 A1 WO2024181924 A1 WO 2024181924A1 SG 2024050114 W SG2024050114 W SG 2024050114W WO 2024181924 A1 WO2024181924 A1 WO 2024181924A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
acid chloride
coating material
fabric
alkyl ketene
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.)
Ceased
Application number
PCT/SG2024/050114
Other languages
English (en)
Inventor
Alok CHAURASIA
Partha Pratim Mitra
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.)
Wilmar Trading Pte Ltd
Original Assignee
Wilmar Trading Pte 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 Wilmar Trading Pte Ltd filed Critical Wilmar Trading Pte Ltd
Publication of WO2024181924A1 publication Critical patent/WO2024181924A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • 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
    • D06M11/32—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 oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/36—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 oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/46—Oxides or hydroxides of elements of Groups 4 or 14 of the Periodic Table; Titanates; Zirconates; Stannates; Plumbates
    • 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
    • D06M13/08—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with halogenated hydrocarbons
    • 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
    • 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
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D06M13/228—Cyclic esters, e.g. lactones
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/01—Stain or soil resistance
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties

Definitions

  • compositions Comprising Fatty Acid Chloride, Alkenyl Succinic Anhydride And/Or Alkyl Ketene Dimer
  • the present invention relates to a coating material comprising a fatty acid chloride, an alkyl ketene dimer and a metal oxide.
  • the present invention also relates to a coating composition comprising a fatty acid chloride, an alkyl ketene dimer, a metal oxide, and a solvent, a method of preparing the coating composition, a method of coating a substrate, use of the coating material or the composition to coat a substrate, a method of conferring hydrophobicity to a textile or fabric comprising the step of applying a coating material comprising alkenyl succinic anhydride to the textile or fabric, a method of softening a textile or fabric comprising the step of contacting a composition comprising fatty acid chloride, an alkenyl succinic anhydride, an alkyl ketene dimer or a mixture thereof and a solvent, with the textile or fabric, the use of alkenyl succinic anhydride to confer hydrophobicity to a textile or fabric and the use of
  • Hydrophobic surfaces have extremely high repellency or extremely low affinity for water. Hydrophobicity of a material is determined by the contact angle of a water droplet on the surface. Generally Hydrophobic surface is understood as a surface that has a water droplet contact angle higher than 90°. Most superhydrophobic coatings made by currently available technologies are not durable. The coatings do not have good adhesion to the substrate, so they are easily scratched off, the coating deteriorates over time, and are often made from non-renewable resources.
  • textiles particularly those made of cellulose fibers after washing becomes hard and coarse and unpleasant to the touch after drying.
  • This undesired hardness generally can be overcome by treating the fabric after washing by rinsing with liquid dispersions of cationic compounds, such as a cationic fabric softening agent dispersed in water.
  • Fabric softener or conditioning compositions are commonly used to impart a fabric softening effect onto a fabric.
  • the fabric softening effect is lost and the fabric again becomes unpleasant to touch after drying, making it necessary to use a fabric softener every time after washing.
  • a coating material comprising a fatty acid chloride, an alkyl ketene dimer and a metal oxide.
  • the coating material may be used as a hydrophobic coating for maintenance, enhancement and protection of various substrates from water, to prevent oxidation of surfaces in air and moisture, especially for cellulosic materials such as wood, leather, cotton textiles, fabric, filters, membranes, and paint, where hydrophobic surfaces are particularly desired.
  • the coating material may have water repellent, self-cleaning, corrosion resistant, antifungal, and/or antibacterial properties.
  • the coating material may have anti-mold properties.
  • the coating may be strongly bonded to the surface of a substrate, rather than simply physically adsorbed onto the surface of the substrate by electrostatic interactions, thereby extending the durability of the hydrophobic effect.
  • the strong bonding may be facilitated by the long fatty acid/ester groups of the components of the coating material, i.e. the fatty acid chloride and alkyl ketene dimer, with the surface.
  • the use of a combination of the fatty acid chloride, alkyl ketene dimer and metal oxide may prevent the degradation of the substrate such as wood, leather, textile or fabric. Degradation of the substrate may occur if only one of fatty acid chloride or alkyl ketene dimer is used to coat the substrate. However, by using a combination of the fatty acid chloride, alkyl ketene dimer and metal oxide, this may be prevented.
  • the metal oxide may facilitate the coating process and provide the substrate with UV- protection.
  • a coating composition comprising a fatty acid chloride, an alkyl ketene dimer, a metal oxide, and a solvent.
  • a method of preparing the coating composition as defined above comprising the step of contacting a fatty acid chloride, an alkyl ketene dimer and a metal oxide with a solvent.
  • there is a method of coating a substrate comprising the step of applying the coating material as defined above or the coating composition as defined above onto the substrate.
  • a method of conferring hydrophobicity to a textile or fabric comprising the step of applying a coating material comprising alkenyl succinic anhydride onto the textile or fabric.
  • a coating material comprising alkenyl succinic anhydride onto the textile or fabric.
  • an alkenyl succinic anhydride to confer hydrophobicity to a textile or fabric.
  • alkenyl succinic anhydride may confer hydrophobicity to a substrate.
  • the alkenyl succinic anhydride may be more reactive or may bind more strongly to a textile or fabric than the alkyl ketene dimer.
  • the alkenyl succinic anhydride may also be less corrosive on the textile or fabric with respect to fatty acid chloride.
  • a method of softening a textile or fabric comprising the step of contacting a composition comprising fatty acid chloride, an alkenyl succinic anhydride, an alkyl ketene dimer or a mixture thereof and a solvent, with the textile or fabric.
  • composition comprising fatty acid chloride, an alkenyl succinic anhydride, an alkyl ketene dimer or a mixture thereof and a solvent, as a textile softener or a fabric softener.
  • relatively low concentrations (less than 10% w/v) of fatty acid chloride, alkenyl succinic anhydride, alkyl ketene dimer or a mixture thereof may have textile or fabric softening properties and may act as an alternative to ammonium-based fabric softeners.
  • fatty acid chloride, alkenyl succinic anhydride, alkyl ketene dimer or a mixture thereof may have long-lasting textile or fabric softening effects compared to conventional textile or fabric softeners.
  • the fatty acid chloride, alkenyl succinic anhydride, alkyl ketene dimer or a mixture thereof may strongly bind to the textile or fabric, rather than being simply physically adsorbed onto the surface of the textile or fabric by electrostatic interactions.
  • the strong bonding may extend the durability of the softening effect of the fabric or textile.
  • the strong bonding may be facilitated by the long fatty acid/anhydride/ester groups of the composition, i.e. the fatty acid chloride, alkenyl succinic anhydride, or alkyl ketene dimer, with the surface.
  • the long fatty acid/ester groups may strongly attach to the surface of the fabric or textile, which may impart lubricity to the fabric or textile by lining up with the fibres. This may be different to the mechanism of conventional fabric softeners which may act by neutralizing the negative charge on the surface of the fabric or the textile.
  • Alkyl as a group or part of a group refers to a straight or branched aliphatic hydrocarbon group.
  • the group may be a terminal group or a bridging group.
  • optionally substituted means the group to which this term refers may be unsubstituted, or may be substituted with one or more groups independently selected from acyl, alkyl, alkenyl, alkynyl, thioalkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkylalkenyl, heterocycloalkyl, cycloalkylheteroalkyl, cycloalkyloxy, cycloalkenyloxy, cycloamino, halo, carboxyl, haloalkyl, haloalkynyl, alkynyloxy, heteroalkyl, heteroalkenyl heteroalkynyl, heteroalkyloxy, hydroxyl, hydroxyalkyl, alkoxy, thioalkoxy, alkenyloxy, haloalkoxy, haloalkenyl, haloalkynyl,
  • softening in the context of this application refers to coating of the surface of a textile or fabric with chemical compounds, to impart a softer and fluffier texture to the textile or fabric.
  • softener should be construed accordingly.
  • the term "about”, in the context of concentrations of components of the formulations, typically means +/- 5% of the stated value, more typically +/- 4% of the stated value, more typically +/- 3% of the stated value, more typically, +/- 2% of the stated value, even more typically +/- 1% of the stated value, and even more typically +/- 0.5% of the stated value.
  • range format may be disclosed in a range format. It should he understood that the description in range format is merely for convenience and brevity and should not be construed as an inflexible limitation on the scope of the disclosed ranges. Accordingly, the description of a range should be considered to have specifically disclosed all the possible sub -ranges as well as individual numerical values within that range. For example, description of a range such as from 1 to 6 should be considered to have specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6 etc., as well as individual numbers within that range, for example, 1, 2, 3, 4, 5, and 6. This applies regardless of the breadth of the range.
  • FIG. 1 refers to a graph showing the contact angle of a 100% cotton cloth that has been coated with the inventive coating after multiple washes without detergent.
  • FIG. 2 refers to a graph showing the contact angle of a 100% cotton cloth that has been coated with the inventive coating after multiple washes with detergent.
  • FIG. 3 refers to a set of photographic images showing a water droplet placed on top of a 100% cotton cloth that has been coated with the inventive coating.
  • FIG. 3AJ shows the cotton cloth coated with the inventive coating before washing
  • FIG. 3BJ shows the cotton cloth coated with the inventive coating after one wash
  • FIG. 3CJ shows the cotton cloth coated with the inventive coating after four washes.
  • FIG. 4 refers to a photographic images showing water droplets placed on Jute coated with the inventive coating
  • a coating material comprising a fatty acid chloride, an alkyl ketene dimer and a metal oxide.
  • the metal oxide may be titanium dioxide or silicon dioxide.
  • the number of carbons in the fatty acid chloride may be in the range of 2 to 60, 2 to 4, 2 to 8, 2 to 16, 2 to 30, 4 to 8, 4 to 16, 4 to 30, 4 to 60, 8 to 16, 8 to 30, 8 to 60, 16 to 30, 16 to 60 or 30 to 60.
  • the fatty acid chloride may comprise an aliphatic fatty acid chloride or an aromatic fatty acid chloride.
  • the fatty acid chloride may have the following formula (1): wherein m is an integer from 1 to 20. m may be an integer from 1 to 5, 1 to 10, 1 to 15, 1 to 20, 5 to 10, 5 to 15, 5 to 20, 10 to 15, 10 to 20 or 15 to 20. m may be 14.
  • the fatty acid chloride may be selected from the group consisting of palmitoyl chloride, stearic acid chloride, lauryl acid chloride and any mixture thereof.
  • the alkyl ketene dimer may have the following formula (II): wherein R 1 and R 2 are independently an optionally substituted alkyl.
  • the optionally substituted alkyl may be substituted or unsubstituted.
  • the optionally substituted alkyl may be a Ci to C20 alkyl, Ci to C5 alkyl, Ci to C10 alkyl, Ci to C15 alkyl, Cs to C10 alkyl, Cs to Cis alkyl, Cs to C20 alkyl, C10 to Cis alkyl, C10 to C20 alkyl or Cis to C20 alkyl.
  • the alkyl ketene dimer may have the following formula (III): wherein a and b are each independently an integer from 1 to 20. a and b may each independently be an integer from 1 to 5, 1 to 10, 1 to 15, 1 to 20, 5 to 10, 5 to 15, 5 to 20, 10 to 15, 10 to 20 or 15 to 20. a and b may independently be 16 or18.
  • the proportion of the functional groups (or a or b as defined above) having a chain length of C18 may be in the range of about 30% to about 95%, about 30% to about 45%, about 30% to about 60%, about 30% to about 75%, about 45% to about 60%, about 45% to about 75%, about 45% to about 95%, about 60% to about 75%, about 60% to about 95% or about 75% to about 95%, based on the total number of functional groups.
  • the alkyl ketene dimer may be alkyl ketene dimer 1895, alkyl ketene dimer 1865, alkyl ketene dimer 1875, or alkyl ketene dimer 1840.
  • the coating material may further comprise an additive selected from the group consisting of an anti-UV agent, anti-bacterial agent, anti-fungal agent, anti-mold, anti-oxidant agent, fragrance and any mixture thereof.
  • the coating material may further comprise a solvent.
  • the solvent may be an organic solvent or an aqueous solvent.
  • the organic solvent may be chloroform, dichloromethane, hexane, ether, petroleum oil, kerosene, methanol, ethanol, butanol, octanol and any mixture thereof.
  • the aqueous solvent may be water.
  • the water may be tap water.
  • a coating composition comprising a fatty acid chloride, an alkyl ketene dimer, a metal oxide, and a solvent.
  • the fatty acid chloride or the alkyl ketene dimer may each be present at a range of about 0.001% w/v to about 10% w/v of the solvent.
  • the fatty acid chloride or the alkyl ketene dimer may each be present at a range of about 0.001% w/v to about 10% w/v, about 0.001% w/v to about 0.01% w/v, about 0.001% w/v to about 0.1% w/v, about 0.001% w/v to about 1% w/v, about 0.01% w/v to about 0.1% w/v, about 0.01% w/v to about 1% w/v, about 0.01% w/v to about 10% w/v, about 0.1% w/v to about 1% w/v, about 0.1% w/v to about 10% w/v, or about 1% w/v to about 10% w/v of the solvent.
  • the metal oxide may be present at a range of about 0.01% w/v to about 0.15% w/v of the solvent.
  • the metal oxide may be present at a range of about 0.01% w/v to about 0.15% w/v, about 0.01% w/v to about 0.05% w/v, about 0.01% w/v to about 0.1% w/v, about 0.05% w/v to about 0.1% w/v, about 0.05% to about 0.15% w/v, or about 0.1% w/v to about 0.15% w/v of the solvent.
  • a method of preparing the coating composition as defined above comprising the step of contacting a fatty acid chloride, an alkyl ketene dimer and a metal oxide with a solvent.
  • the method may further comprise the step of adding an additive selected from the group consisting of an anti-UV agent, anti-bacterial agent, anti-fungal agent, anti-mold agent, anti-oxidant agent, fragrance and any mixture thereof.
  • the additive may be added at an amount of about 0.001% w/v to about 1% w/v, about 0.001% w/v to about 0.01% w/v, about 0.001% w/v to about 0.1% w/v, about 0.01% w/v to about 0.1% w/v, about 0.01% w/v to about 1% w/v, or about 0.1% w/v to about 1% w/v.
  • the method may comprise the step of removing the solvent to obtain the coating material as defined above.
  • the step of removing the solvent may comprise drying.
  • the drying may be by heating.
  • the drying may be performed at room temperature or at a temperature in the range of about 100 °C to about 115 °C, about 100 °C to about 105 °C, about 100 °C to about 110 °C, about 105 °C to about 100 °C, about 105 °C to about 115 °C, or about 110 °C to about 115 °C.
  • the heating may facilitate the formation of the bond between the coating material and a substrate, as well as the drying of the coating material.
  • a method of coating a substrate comprising the step of applying the coating material as defined above or the coating composition as defined above onto the substrate.
  • the applying step may comprise dipping the substrate in the coating composition.
  • the dipping step may be performed for a duration in the range of about 0.001 seconds to about 10 hours, about 0.001 seconds to about 1 second, about 0.001 seconds to about 1 minute, about 0.001 seconds to about 1 hour, about 1 second to about 1 minute, about 1 second to about 1 hour, about 1 second to about 10 hours, about 1 minute to about 1 hour, about 1 minute to about 10 hours, or about 1 hour to about 10 hours.
  • the method may further comprise the step of heating the coating material.
  • the heating may be performed at a temperature in the range of about 60 °C to about 120 °C, about 60 °C to about 80 °C, about 60 °C to about 100 °C, about 80 °C to about 100 °C, about 80 °C to about 120 °C, or about 100 °C to about 120 °C.
  • the heating step may activate the coating material to bind with the substrate.
  • the coating material may bind to the surface of the substrate by covalent bonding, ionic bonding, hydrogen bonding, Van der Waals forces, Keesom forces, or London dispersion forces..
  • the coating material may be strongly bonded onto the substrate by covalent bonding, ionic bonding, hydrogen bonding, Van der Waals forces, Keesom forces, or London dispersion forces.
  • the coating material may confer hydrophobicity to the substrate.
  • the substrate may comprise hydroxy or amine functional groups on the surface.
  • the substrate may be wood, leather, Jute fiber, Hemp fiber, textile, fabric, or any mixture thereof.
  • the leather may be natural, synthetic or a combination thereof.
  • the fabric or textile may be natural, synthetic or a combination thereof.
  • the textile or fabric may be woven, knitted or a combination thereof.
  • the textile or fabric may comprise cellulose, chiffon, cotton, crepe, nylon, silk, polyester, rayon, wool, flax fibre, linen, pile, imitation fur, velvet or any mixture thereof.
  • the textile or fabric may comprise cellulose fibres.
  • the textile or fabric may comprise cellulose or cotton.
  • the fatty acid chloride or the alkyl ketene dimer may each be present at a range of about 0.001% w/v to about 3% w/v in the coating.
  • the alkenyl succinic anhydride may have the following formula (IV): wherein R 3 and R 4 are independently an optionally substituted alkyl.
  • the optionally substituted alkyl may be substituted or unsubstituted.
  • the optionally substituted alkyl may be a Ci to C25 alkyl, Ci to Cs alkyl, Ci to C10 alkyl, Ci to C15 alkyl, Ci to C20 alkyl, Cs to Cm alkyl, Cs to Cis alkyl, Cs to C20 alkyl, Cs to C25 alkyl, C10 to Cis alkyl, Cm to C20 alkyl, C10 to C25 alkyl, Cis to C20 alkyl, Cis to C25 alkyl or C20 to C25 alkyl.
  • the alkenyl succinic anhydride may have the following formula (V) : wherein c and d are each independently an integer from 1 to 24. c and d may each independently be an integer of from 1 to 5, 1 to 10, 1 to 15, 1 to 20, 1 to 24, 5 to 10, 5 to 15, 5 to 20, 5 to 24, 10 to 15, 10 to 20, 10 to 24, 15 to 20, 15 to 24 or 20 to 24. c and d may each independently be 12 or 14.
  • the alkenyl succinic anhydride may comprise a mixture of different alkenyl succinic anhydrides.
  • the alkenyl succinic anhydride may comprise at least partially branched carbon chains.
  • the alkenyl succinic acid may comprise isomerized carbon chains.
  • the alkenyl succinic anhydride may comprise a mixture of Cig to Cis partially branched and isomerized carbon chains.
  • the coating material comprising alkenyl succinic anhydride may further comprise an alkyl ketene dimer, a fatty acid chloride, and any combination thereof.
  • the coating material comprising alkenyl succinic anhydride may further comprise an alkyl ketene dimer.
  • the coating material comprising alkenyl succinic anhydride may further comprise a fatty acid chloride.
  • the coating material comprising alkenyl succinic anhydride may further comprise an alkyl ketene dimer and fatty acid chloride.
  • a method of softening a textile or fabric comprising the step of contacting a composition comprising a fatty acid chloride, an alkenyl succinic anhydride, an alkyl ketene dimer or a mixture thereof and a solvent, with the textile or fabric.
  • the composition may comprise a fatty acid chloride.
  • the composition may comprise an alkenyl succinic anhydride.
  • the composition may comprise an alkyl ketene dimer.
  • the composition may comprise a fatty acid chloride and an alkenyl succinic anhydride.
  • the composition may comprise a fatty acid chloride and alkyl ketene dimer.
  • the composition may comprise an alkenyl succinic anhydride and an alkyl ketene dimer.
  • the composition may comprise a fatty acid chloride, an alkenyl succinic anhydride and an alkyl ketene dimer.
  • the contacting step may comprise dipping the textile or fabric in the composition comprising the fatty acid chloride, an alkenyl succinic anhydride, alkyl ketene dimer or a mixture thereof and the solvent.
  • the fatty acid chloride, an alkenyl succinic anhydride or the alkyl ketene dimer may each be present at a range of about 0.001% w/v to about 0.5% w/v of the solvent.
  • the fatty acid chloride, an alkenyl succinic anhydride or the alkyl ketene dimer may each be present at a range of about 0.001% w/v to about 0.5% w/v, about 0.001% w/v to about 0.005% w/v, about 0.001% w/v to about 0.01% w/v, about 0.01% w/v to about 0.05% w/v, about 0.001% w/v to about 0.1% w/v, about 0.005% w/v to about 0.01% w/v, about 0.005% w/v to about 0.05% w/v, about 0.005% w/v to about 0.1% w/v, about 0.005% w/v to about 0.5% w/v, about 0.01% w/v to about 0.05% w/v, about 0.01% w/v to about 0.5% w/v, about 0.01% w/v to about 0.05% w/v, about 0.01%
  • the method of may further comprise the step of adding a metal oxide to the composition, prior to contacting with the textile or fabric.
  • the metal oxide may be present at a range of about 0.01% w/v to about 0.15% w/v of the solvent.
  • the method may further comprise adding an additive selected from the group consisting of an anti-UV agent, anti-bacterial agent, anti-fungal agent, anti-mold agent, anti-oxidant agent, fragrance and any mixture thereof to the composition, prior to contacting with the textile or fabric.
  • an additive selected from the group consisting of an anti-UV agent, anti-bacterial agent, anti-fungal agent, anti-mold agent, anti-oxidant agent, fragrance and any mixture thereof to the composition, prior to contacting with the textile or fabric.
  • the dipping step may be performed for a duration in the range of aboutO.001 seconds to about 10 hours, about 0.001 seconds to about 1 second, about 0.001 seconds to about 1 minute, about 0.001 seconds to about 1 hour, about 1 second to about 1 minute, about 1 second to about 1 hour, about 1 second to about 10 hours, about 1 minute to about 1 hour, about 1 minute to about 10 hours, or about 1 hour to about 10 hours.
  • the method may further comprise the step of heating the composition.
  • the heating may be performed at a temperature in the range of about 60 °C to about 120 °C, about 60 °C to about 80 °C, about 60 °C to about 100 °C, about 80 °C to about 100 °C, about 80 °C to about 120 °C, or about 100 °C to about 120 °C.
  • the heating step may activate the coating material to bind with the substrate.
  • the coating material may bind to the surface of the substrate by covalent bonding, ionic bonding, hydrogen bonding, Van der Waals forces, Keesom forces, or London dispersion forces.
  • the heating step may facilitate the formation of the bond between the coating material and the substr ate, as well as the drying of the coating material.
  • an alkenyl succinic anhydride to confer hydrophobicity to a textile or fabric.
  • composition comprising fatty acid chloride, an alkenyl succinic anhydride, an alkyl ketene dimer or a mixture thereof and a solvent, as a textile softener or a fabric softener.
  • the fatty acid chloride, an alkenyl succinic anhydride, the alkyl ketene dimer or a mixture thereof may be strongly bonded to the textile or fabric by covalent bonding, ionic bonding, hydrogen bonding, Van der Waals forces, Keesom forces, or London dispersion forces.
  • the fabric or textile may be natural, synthetic or a combination thereof.
  • the textile or fabric may be woven, knitted or a combination thereof.
  • the textile or fabric may comprise cellulose, chiffon, cotton, crepe, nylon, silk, polyester, rayon, wool, flax fibre, linen, pile, imitation fur, velvet or any mixture thereof.
  • the textile or fabric may comprise cellulose fibres.
  • the textile or fabric may comprise cellulose or cotton.
  • the cellulose may be in the form of Hemp or Jute.
  • a fatty acid chloride solution was prepared by adding 18 g of palmitoyl chloride (Wilmar (China) Olco Co., Ltd, China) in 300 ml of dichloromethane (DCM) (Sigma-Aldrich, St. Louis, Missouri, USA). Then, a cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the solution for 3 minutes. After that, the cotton cloth was taken out and washed with DCM four times, to remove any unbounded palmitoyl chloride from the treated cloth. The cloth was dried at 80 °C for 10 minutes under normal air.
  • DCM dichloromethane
  • a fatty acid chloride (palmitoyl chloride) solution was prepared by adding 9 g of palmitoyl chloride in 300 ml of dichloromcthanc (DCM) in a similar manner to Example 2.
  • DCM dichloromcthanc
  • 0.27 g TiO> nanoparticlcs (Sigma-Aldrich, St. Lous, Missouri, USA) having an average particle size of less than 100 nm, was added.
  • a 100% cotton cloth (3 inch by 2 inch) was immersed in the solution for 3 minutes. After that, the cotton cloth was taken out and washed with DCM 4 times, to remove any unbounded palmitoyl chloride from the treated cloth.
  • the cloth was dried at 80 °C for 10 minutes under normal air.
  • alkyl ketene dimer solution was prepared by adding 18 g of alkyl ketene dimer 1895 (Wilmar, Singapore) in 300 ml of dichloromethane (DCM) (Sigma-Aldrich, St. Louis, Missouri, USA). Then, a 100% cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the solution for 3 minutes. After that, the cotton cloth was dried at 80 °C for 10 minutes under normal air, and after that was taken out and washed with DCM 4 times, to remove any unbounded alkyl ketene dimer from the treated cloth. The cloth was dried again at 80 °C for 10 minutes under normal air.
  • DCM dichloromethane
  • Example 2 In a similar manner to Example 1 , excellent hydrophobic character was observed and it was found that even after 6 washes, the contact angle remained above 140°. The fact that hydrophobicity was observed even after 6 washes showed that the bond between the coating and the cotton cloth was strong.
  • Example 4 The same procedures as Example 4 was repeated but with 9 g alkyl ketene dimer 1895 instead of 18 g of alkyl ketene dimer 1895.
  • An alkyl ketene dimer solution was prepared by adding 9 g of alkyl ketene dimer 1895 in 300 ml of dichloromethane (DCM) in a similar manner to Example 5.
  • DCM dichloromethane
  • 0.27 g TiCb nanoparticles Sigma-Aldrich, St. Lous, Missouri, USA
  • a 100% cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the solution for 3 minutes.
  • the cotton cloth was dried at 80 °C for 10 minutes under normal air, and after that, the cotton cloth was taken out and washed with DCM 4 times, to remove any unbounded alkyl ketene dimer from the treated cloth.
  • the cotton cloth was dried again at 80 °C for 10 minutes under normal air.
  • An alternative example of the coating was prepared by dissolving 3 g of alkyl ketene dimer 1895 in 100 mL of dichloromcthanc (DCM). Then, a 100% cotton cloth (3 inch by 2 inch) or Jute was dipped into the solution for 3 minutes and taken out to be dried, by keeping it at 80 °C for 10 minutes.
  • DCM dichloromcthanc
  • the contact angle of the cloth was found to be about 150 °. A water drop placed on the cloth was stable and was not absorbed into the cloth even after 1 hour.
  • Washing was firstly performed with normal tap water without any detergent. Each wash cycle was performed for 20 minutes at 180 rpm using a tergotometer, followed by drying the cloth in an oven at 80 °C for 10 minutes under normal air. The contact angle was measured after each wash, as shown in Fig. 1.
  • washing was then performed with normal tap water and detergent (P&G). Specifically, 2.0 g of P&G dynamo detergent was dissolved in one liter of water. Each wash cycle was performed for 20 minutes at 180 rpm using a tergotometer, followed by drying the cloth in an oven at 80 °C for 10 minutes under normal air. The contact angle was measured after each wash, as shown in Fig. 2.
  • P&G normal tap water and detergent
  • alkenyl succinic anhydride solution was prepared by adding 18 g of alkenyl succinic anhydride having a mixture of C H, to Cis partially branched and isomerized carbon chains (Wilmar, Singapore) in 300 ml of dichloromethane (DCM) (Sigma-Aldrich, St. Louis, Missouri, USA).
  • DCM dichloromethane
  • a cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the solution for 3 minutes. After that, the cotton cloth was taken out and washed with DCM four times, to remove any unbounded alkenyl succinic anhydride from the heated cloth. The cloth was dried at 80 °C for 10 minutes under normal air.
  • alkenyl succinic anhydride alkyl ketene dimer (50:50 by weight) solution was prepared by adding 9 g of alkenyl succinic anhydride having a mixture of Ci6 to Cis partially branched and isomerized carbon chains and 9 g of alkyl ketene dimer 1895 in 300 ml of dichloromethane (DCM) (Sigma- Aldrich, St. Louis, Missouri, USA).
  • DCM dichloromethane
  • a cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the solution for 3 minutes. After that, the cotton cloth was taken out and washed with DCM four times, to remove any unbounded alkenyl succinic anhydride or alkyl ketene dimer from the treated cloth. The cloth was dried at 80 °C for 10 minutes under normal air.
  • Example 2 In a similar manner to Example 1 , excellent hydrophobic character was observed and it was found that even after 6 washes, the contact angle remained above 140°. The fact that hydrophobicity was observed even after 6 washes showed that the bond between the coating and the cotton cloth was strong.
  • alkenyl succinic anhydride alkyl ketene dimer (25:75 by weight) solution was prepared by adding 4.5 g of alkenyl succinic anhydride having a mixture of Cm to Cis partially branched and isomerized carbon chains and 13.5 g of alkyl ketene dimer 1895 in 300 ml of dichloromethane (DCM) (Sigma-Aldrich, St. Louis, Missouri, USA).
  • DCM dichloromethane
  • a cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the solution for 3 minutes. After that, the cotton cloth was taken out and washed with DCM four times, to remove any unbounded alkenyl succinic anhydride or alkyl ketene dimer from the treated cloth. The cloth was dried at 80 °C for 10 minutes under normal air.
  • Example 2 In a similar manner to Example 1 , excellent hydrophobic character was observed and it was found that even after 6 washes, the contact angle remained above 140°. The fact that hydrophobicity was observed even after 6 washes showed that the bond between the coating and the cotton cloth was strong.
  • aqueous alkenyl succinic anhydride alkyl ketene dimer (50:50 by weight) emulsion was prepared by adding 9 g of aqueous alkenyl succinic anhydride having a mixture of Cie to Cis partially branched and isomerized carbon chains and 9 g of alkyl ketene dimer 1895 in 300 ml of deionized water.
  • a cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the emulsion for 3 minutes. After that, the cotton cloth was taken out and washed with deionized water four times, to remove any unbounded aqueous alkenyl succinic anhydride or alkyl ketene dimer from the treated cloth. The cloth was dried at 80 °C for 10 minutes under normal air.
  • a fatty acid chloride solution was prepared by adding 3 g of palmitoyl chloride (Wilmar (China) Oleo Co., Ltd, China) in 300 ml of dichloromethane (DCM) (Sigma- Aldrich, St. Louis, Missouri, USA). Then, a 100% cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the solution for 3 minutes. After that, the cotton cloth was taken out and washed with DCM 4 times, to remove any unbounded palmitoyl chloride from the treated cloth. The cloth was dried at 80 °C for 10 minutes under normal air.
  • DCM dichloromethane
  • alkyl ketene dimer solution was prepared by adding 3 g of alkyl ketene dimer 1895 (Wilmar, Singapore) in 300 ml of dichloromcthanc (DCM) (Sigma-Aldrich, St. Louis, Missouri). Then, a 100% cotton cloth (3 inch by 2 inch) (purchased from a market) was immersed in the solution for 3 minutes. After that, the cloth was dried at 80 °C for 10 minutes under normal air. After that, the cotton cloth was taken out and washed with DCM 4 times, to remove any unbounded alkyl ketene dimer from the treated cloth. After that, the cloth was dried at 80 °C for 10 minutes under normal air.
  • DCM dichloromcthanc
  • Example 14 Fabric Softener C (Sample-1)
  • alkyl ketene dimer emulsion was prepared by adding 6 g of alkyl ketene dimer 1895 (Wilmar, Singapore) in 100 ml of tap water to form an aqueous emulsion solution and was denoted Sample-1. Sample-1 and its diluents were tested for fabric softness and smoothness after application on 100% cotton woven fabric (white) (3 inch by 2 inch) after prewashing with AATCC Standard Reference detergent powder (without optical brightener).
  • the cotton woven fabric was immersed in Sample- 1 and its diluents as outlined in Table 1 for less than 1 minute at room temperature, and excess solution was removed by padding.
  • An M:L ratio (ratio of mass (in grams) of fabric : volume (in mL) of sample solution) of 1:30 was used. That is, for 1 gram of fabric, 30 mL of sample solution. For example, if the weight of an A4 sized fabric was 10 grams, then it was treated with 300 mL of sample solution at a particular concentration.
  • the fabric used was 100% Cotton woven fabric (RFD) having a weight of approximately 155 grams per square meter. RFD stands for Ready for Dyeing (bleach unfinished cloth).
  • the treated cotton woven fabric was then dried at 105 °C to 108 °C for 3 minutes using hot air.
  • Panelist No.l H>E>D>G>F>C>B>A
  • Samples H and E were evaluated to have the most softness and/or smoothness, while Sample A was evaluated to have the least softness and/or smoothness.
  • the coating material and the coating composition as defined above may be used to impart hydrophobicity to a substrate such as wood, leather, textile, fabric and any mixture thereof.
  • a composition comprising fatty acid chloride, an alkenyl succinic anhydride, an alkyl ketene dimer or a mixture thereof and a solvent, may be useful as a textile softener or a fabric softener.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention concerne un matériau de revêtement comprenant un chlorure d'acide gras, un dimère d'alkyle-cétène et un oxyde métallique. La présente invention concerne également une composition de revêtement comprenant un chlorure d'acide gras, un dimère d'alkyle-cétène, un oxyde métallique et un solvant, un procédé de préparation de la composition de revêtement, un procédé de revêtement d'un substrat, l'utilisation du matériau de revêtement ou de la composition pour revêtir un substrat, un procédé pour conférer un caractère hydrophobe à un substrat comprenant l'étape consistant à appliquer un matériau du revêtement comprenant de l'anhydride alcényle succinique sur le substrat, un procédé de ramollissement d'un textile ou d'un tissu comprenant l'étape de mise en contact d'une composition comprenant du chlorure d'acide gras, un anhydride alcényle succinique, un dimère d'alkyle-cétène ou un mélange de ceux-ci et un solvant, avec le textile ou le tissu, l'utilisation d'anhydride alcényle succinique pour conférer un caractère hydrophobe d'un substrat et l'utilisation d'une composition comprenant du chlorure d'acide gras, un anhydride alcényle succinique, un dimère d'alkyle-cétène ou un mélange de ceux-ci et un solvant, en tant qu'adoucissant textile ou adoucisseur de tissu.
PCT/SG2024/050114 2023-02-28 2024-02-28 Compositions comprenant du chlorure d'acide gras, de l'anhydride alcényle succinique et/ou un dimère d'alkyle-cétène Ceased WO2024181924A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SG10202300533W 2023-02-28
SG10202300533W 2023-02-28

Publications (1)

Publication Number Publication Date
WO2024181924A1 true WO2024181924A1 (fr) 2024-09-06

Family

ID=92590330

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SG2024/050114 Ceased WO2024181924A1 (fr) 2023-02-28 2024-02-28 Compositions comprenant du chlorure d'acide gras, de l'anhydride alcényle succinique et/ou un dimère d'alkyle-cétène

Country Status (1)

Country Link
WO (1) WO2024181924A1 (fr)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2182366A (en) * 1985-10-22 1987-05-13 Kemira Oy Neutral size
GB2221928A (en) * 1988-08-17 1990-02-21 Stephenson Group Waterproofing treatment of textile materials
WO1994018389A1 (fr) * 1993-02-15 1994-08-18 Eka Nobel Ab Procede de reduction du contenu de solvant organique dans des agents hydrophophes reagissant avec la cellulose
US5447689A (en) * 1994-03-01 1995-09-05 Actimed Laboratories, Inc. Method and apparatus for flow control
WO1999041452A1 (fr) * 1998-02-17 1999-08-19 Hercules Incorporated Collage du papier
US6342268B1 (en) * 1997-08-14 2002-01-29 Daniel Samain Method for treating a solid material to make it hydrophobic, material obtained and uses
US20160168696A1 (en) * 2013-07-26 2016-06-16 Institut Polytechnique De Grenoble Method for forming a hydrophobic layer
WO2020100101A1 (fr) * 2018-11-16 2020-05-22 Stora Enso Oyj Procédé pour rendre hydrophobe un substrat de cellulose à l'aide d'un halogénure d'acide gras
WO2021165898A1 (fr) * 2020-02-21 2021-08-26 Stora Enso Oyj Substrat à base de cellulose multicouche résistant à l'eau

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2182366A (en) * 1985-10-22 1987-05-13 Kemira Oy Neutral size
GB2221928A (en) * 1988-08-17 1990-02-21 Stephenson Group Waterproofing treatment of textile materials
WO1994018389A1 (fr) * 1993-02-15 1994-08-18 Eka Nobel Ab Procede de reduction du contenu de solvant organique dans des agents hydrophophes reagissant avec la cellulose
US5447689A (en) * 1994-03-01 1995-09-05 Actimed Laboratories, Inc. Method and apparatus for flow control
US6342268B1 (en) * 1997-08-14 2002-01-29 Daniel Samain Method for treating a solid material to make it hydrophobic, material obtained and uses
WO1999041452A1 (fr) * 1998-02-17 1999-08-19 Hercules Incorporated Collage du papier
US20160168696A1 (en) * 2013-07-26 2016-06-16 Institut Polytechnique De Grenoble Method for forming a hydrophobic layer
WO2020100101A1 (fr) * 2018-11-16 2020-05-22 Stora Enso Oyj Procédé pour rendre hydrophobe un substrat de cellulose à l'aide d'un halogénure d'acide gras
WO2021165898A1 (fr) * 2020-02-21 2021-08-26 Stora Enso Oyj Substrat à base de cellulose multicouche résistant à l'eau

Similar Documents

Publication Publication Date Title
CN105164332B (zh) 获得斥水性和或水溶性污物排斥性纺织品的方法和组合物
US4207071A (en) Durable modification of fibrous substrates using a polyoxyethylene-containing silane and articles therefrom
US6872424B2 (en) Durable finishes for textiles
Ibrahim et al. Functional finishes of stretch cotton fabrics
US4007305A (en) Method of imparting nondurable soil release and soil repellency properties to textile materials
US7858539B2 (en) Processes for generating halamine compounds on textile substrates to produce antimicrobial finish
Fahmy et al. Synthesis of new silicone-based adducts to functionalize cotton fabric
US6827746B2 (en) Textile finishing process
WO2011005963A1 (fr) Procédé de réduction des plis à l'aide d'une composition d'entretien de textile
EP2203505A2 (fr) Procédé de modification de la surface d'un textile synthétique
WO2024181924A1 (fr) Compositions comprenant du chlorure d'acide gras, de l'anhydride alcényle succinique et/ou un dimère d'alkyle-cétène
WO2011111658A1 (fr) Procédé de traitement de fibre cellulosique ou de produit en fibre cellulosique
EP1141469A1 (fr) Procede d'appretage de textiles
KR101940730B1 (ko) 4차화된 헤테로고리기를 포함한 폴리실록산
DE102009014164A1 (de) Multifunktionelles Beschichtungsmittel
US3193397A (en) Phosphonitrilic flameproofing materials
AU2017269291A1 (en) Compositions for the treatment of articles, and articles treated thereform
DE102007054627A1 (de) Wasserverträgliche Sole zur Beschichtung verschiedener Substrate
DE102006024727A1 (de) Mit Wasser verdünnbares Konzentrat zur Beschichtung verschiedener Substrate
Singh et al. Multifunctional modification of cotton fabric for antimicrobial, flame-retardant and oleophobic properties
CN114144554A (zh) 纤维用抗静电加工药剂及其利用
JP4777000B2 (ja) 外干し洗濯物への付着花粉の破裂抑制及び花粉の付着抑制方法
WO2024141950A1 (fr) Dérivé cellulosique, compositions et utilisations associées
US20090176094A1 (en) Fibre Modified By Application Of An Organosiliconate Agent, A Fibre Modifying Agent Comprising An Organosilikonate and A Method of Modifying A Fibre With Said Agent
JP2025177244A (ja) 繊維用帯電防止加工剤、帯電防止加工繊維及び帯電防止加工繊維の製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24764287

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE