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WO2019115392A1 - Formulations antisalissure pour applications textiles - Google Patents

Formulations antisalissure pour applications textiles Download PDF

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Publication number
WO2019115392A1
WO2019115392A1 PCT/EP2018/083995 EP2018083995W WO2019115392A1 WO 2019115392 A1 WO2019115392 A1 WO 2019115392A1 EP 2018083995 W EP2018083995 W EP 2018083995W WO 2019115392 A1 WO2019115392 A1 WO 2019115392A1
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Prior art keywords
acrylate
hydrophobic
monomeric
carbon atoms
range
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PCT/EP2018/083995
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English (en)
Inventor
Helmut Sieber
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HeiQ mATERIALS AG
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HeiQ mATERIALS AG
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Publication of WO2019115392A1 publication Critical patent/WO2019115392A1/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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • D06M15/29—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides containing a N-methylol group or an etherified N-methylol group; containing a N-aminomethylene group; containing a N-sulfidomethylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/273—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having epoxy groups
    • 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
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/327—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • 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

Definitions

  • the present invention relates to textile fiber finishing fabric care formulations imparting improved soil release properties to the corresponding textile fiber product.
  • the present invention furthermore relates to methods of making corresponding textile fiber finishing formulations and uses thereof.
  • Fabric especially clothing, can become soiled by a range of substances including hydrophobic stains (grease, oil) but also hydrophilic stains. Avoiding lasting stain attachment as well as removal of soils and in particular oily stains is a continuing aim for textile manufacturing and for cleaning detergent manufacturers. Despite the use of many- different surfactants and combinations thereof, the products do not achieve complete removal in particular of greasy/oily stains independent of the textile basic material. A further requirement in the textile field is instant or at least rapid stain removal at the moment of the staining.
  • Treating the fabric during manufacturing of the fibres or the clothing so that stains and soils do not effectively bind to the fabric or fiber surface may on the one hand avoid attachment of the staining substances in the first place and further provide improved cleaning of fabrics. According to this approach, the staining substances do not bind or form strong physicochemical interactions with the fabric surface and can be more easily removed from the fabric surface upon laundering or another treatment process.
  • one approach is to treat the fabric or rather the fiber surface during the manufacturing process to form the desired fabric or fiber surface exhibiting the desired stain repellency.
  • one drawback may be the reduced stain repellency over time due to exposure to adverse environmental effects and washing.
  • a second approach may be to repeatedly treat the fabric or fiber surface during the laundering or other fabric treatment process. With this approach, the stain repellency characteristics may be renewed with each treatment or after a specific time, however repeated application leads to increased costs and treatment material waste.
  • One state-of-the-art molecular system providing anti-staining properties to textile surfaces are perfluorinated hydrocarbon systems with for example 6 or 8 carbon atoms. The systems at the time provide for water repellency, oil repellency as well as soil release, i.e. ease of removal of oily stains. However, in particular for environmental reasons the perfluorinated hydrocarbon systems, in as far as not banned already, need to be replaced by other chemistries.
  • DE 1719359 proposes a method for improving the soil-release properties of textiles.
  • Acidic hydrophilic acrylate based fabric care formulations are described to impart soil release properties to fabrics, however at the same time to impart an undesired feel of stiffness.
  • the document proposes to solve that problem by adding to such an acidic hydrophilic acrylate based fabric care formulation in a mixture long chain fatty acid compounds or the corresponding alcohols, thereby achieving anti-staining properties as well as soft feel.
  • US 5763022 provides a process for improving the resistance to solvents in finishing and stabilizing fiber materials with textile binders, wherein the textile binder used is an aqueous copolymer dispersion or a redispersible copolymer powder of acrylamide based copolymers, containing (a) one or more monomer units from the group consisting of vinyl esters of unbranched or branched carboxylic acids with 1 to 12 carbon atoms, esters of acrylic acid and methacrylic acid with unbranched or branched alcohols with 1 to 12 carbon atoms, vinyl aromatics, vinyl halides and alpha-olefins, and (b) 0.3 to 10 wt %, relative to the total weight of the copolymer, of one or more N-(alkoxymethyl)- acrylamides or N-(alkoxymethyl)methacrylamides with a C1-C6 alkyl residue, or mixtures of these N-(alkoxymethyl)-meth(acrylamides with N-
  • JPS5040897 and correspondingly GB 1473362 disclose how cellulosic fibre products are rendered resistant to wet and dry creasing, shrinkage and surface abrasion, rendered soft to the touch and given increased tensile strength by treatment with a solution or dispersion of a filmforming glycidyl-containing thermoplastic random polymer, drying the product and then heating it to clear the oxirane bond of the glycidyl group.
  • the polymer is a random copolymer of 1 to 55% of one or more monoethylenically unsaturated monomers containing a glycidyl group with one or more other ethylenically unsaturated monomers.
  • the glycidyl monomers are glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether, glycidyl crotonate, dichloro glycidyl acrylate, vinyl glycidyl ether or other ester or ether.
  • the other monomer is preferably 2-ethylhexyl acrylate but many other olefins, vinyl compounds and unsaturated acids, esters and amides are specified.
  • the oxirane bond is cleared by heating in the presence of an acid catalyst to 120 to 190 C for 0.5 to 15 minutes, preferably whilst being pin centred 15% in the weft direction. No block copolymers are disclosed and no soil release properties.
  • the proposed formulation systems shall be efficient as concerns the anti-staining, in the sense that the fabric gets less prone to get stained, and that once it is stained it is easy to remove the corresponding staining during the laundry process.
  • the proposed formulations shall in addition to that be stable and easy to apply for the actual fabric treatment process, and also be stable for the storage, i.e. for the time between manufacturing and actual use.
  • the active ingredient of the corresponding formulation to be deposited on the fibers shall be resistant to be removed during laundry cycles, so it shall have a lasting effect on the fabric and should not have to be renewed.
  • the present invention thus relates to a textile treatment formulation to impart anti-staining properties to fibers or garments.
  • the proposed formulation contains an effective amount of a block-copolymer (I) or a mixture thereof, wherein the block-copolymer (I) has the following structure (and preferably consists only of these building blocks):
  • HO is a hydrophobic block, based on or formed exclusively from at least one monomeric hydrophobic building block. This block typically forms the innermost core of a resulting core-shell particle.
  • HI is a hydrophilic block, based on or formed exclusively from at least one monomeric hydrophilic acrylate building block. This block typically forms an intermediate water- swellable core layer of a resulting core-shell particle.
  • the swellablitity is believed to contribute to the anti-soiling property imparted by the system: during the washing cycle the core-shell particle swells and releases the soling substances.
  • HO_RT is a hydrophobic reactive tail block, based on or formed exclusively from at least one monomeric hydrophobic building block as well as at least one bifunctional reactive monomeric acrylate or acrylamide building block.
  • the reactive tail is adapted to either react with functional groups on the surface of the fiber, or to react with functional groups of other chemicals on the surface of the fiber.
  • the attachment by way of the reactive tails can also be by way of electrostatic interaction, van der Waals interactions or hydrogen bonding instead of or in addition to the chemical bond.
  • This block typically forms the outermost shell of a resulting core-shell particle.
  • fabric care compositions includes compositions and formulations designed for treating textiles and fabrics, such as, but not limited to, fabric softening compositions, fabric enhancing compositions, fabric freshening compositions.
  • the term "containing” means various components conjointly employed in the preparation of the formulation, so it does not exclude the presence of other chemicals in the formulation. Equally, in the present context, the terms “include”, “includes” and “including” are meant to be non- limiting.
  • the formulation is a dispersion of the block- copolymer (I) and water without additional constituents or just with a deposition aid, typically such a master formulation is then, before use, supplemented with additional ingredients for the actual application step to the fabric.
  • fabric non-specifically and may refer to any type of flexible material consisting of a network of natural or artificial fibers, including natural, artificial, and synthetic fibers, such as, but not limited to, cotton, linen, wool, polyester, silk, hemp, flax, lyocell, rayon, jute, polyamide, modacrylic, olefmic, acrylic, or a mixture and/or blend thereof.
  • the term "deposition aid” means a compound or composition that assists in deposition of a substance, in particular of the block-copolymer (I), typically as a core-shell particle, on a surface, such as the surface of a fabric or fiber during a treatment process. Deposition aids may allow for or at least assist complete and uniform deposition of the substance on the fabric surface.
  • hydrophobic means that the corresponding block has the tendency to mix with and/or contact alkanes, oils, fats, and greasy substances, this at least to an extent which is more pronounced than a block that is designated hydrophilic in the present context. It is therefore a block whose interactions with oil or other hydrophobic solvents substances are more thermodynamically favorable than their interactions with water and other polar substances.
  • the term "hydrophilic" means that the corresponding block has the tendency to mix with and/or contact water and other polar substances, this at least to an extent which is more pronounced than a block that is designated hydrophobic in the present context. It is therefore a block whose interactions with water and other polar substances are more thermodynamically favorable than their interactions with oil or other hydrophobic solvents.
  • the proposed block-copolymer (I) is free from halogen containing building blocks, in particular free from perhalogen building blocks and/or from siloxane or polysiloxane building blocks.
  • the bifunctional reactive monomeric acrylate or acrylamide building block in (HO_RT) is selected from the group consisting of N-alkylol acrylamide, epoxy-acrylate, or mixtures thereof.
  • the alkyl group in the N-alkylol acrylamide is typically a linear saturated alkyl chain with 1 - 10, preferably 1 - 3 carbon atoms.
  • the bifunctional reactive monomeric acrylate or acrylamide building block in (HO_RT) is selected from the group consisting of glycidyl acrylate, glycidyl methacrylate, N-methylol acrylamide, N-methylol methacrylamide, or mixtures thereof.
  • glycidyl based systems is preferred.
  • glycidyl methacrylate alone or N-methylol methacrylamide alone, most preferably glycidyl methacrylate is used.
  • the average number of monomeric acrylate or acrylamide building blocks within (HO_RT) is preferably in the range of 1-20, more preferably in the range of 2-15.
  • the at least one monomeric hydrophobic building block in (HO_RT) is selected from at least one hydrophobic acrylate and/or hydrophobic vinylester monomer.
  • the at least one monomeric hydrophobic building block in (HO RT) can also be based on or formed exclusively from at least two different hydrophobic acrylate and/or hydrophobic vinylester monomers.
  • the weight ratio between the two different hydrophobic acrylate and/or hydrophobic vinylester monomers in (HO_RT) is in the range of 2:1 - 1 :2, preferably in the range of 1.25:1 - 1 : 1.25.
  • the two different hydrophobic acrylate and/or hydrophobic vinylester monomers in (HO RT) differ in their hydrophobicity.
  • the monomeric hydrophobic building block in (FIO_RT) can be based on or formed exclusively from at least one hydrophobic acrylate and/or hydrophobic vinylester monomer as well as at least one more hydrophilic acrylate and/or more hydrophilic vinylester monomer.
  • the monomeric hydrophobic building block in (FIO_RT) can also be based on or formed exclusively from at least two different hydrophobic acrylate and/or hydrophobic vinylester monomers as well as at least one hydrophilic acrylate and/or hydrophilic vinylester monomer.
  • the at least one monomeric hydrophobic building block in (HO_RT) may also be preferably selected from alkyl acrylate and alkyl methacrylate monomers, wherein the alkyl chain is a saturated branched or linear alkyl group with 3-12 carbon atoms, preferably with 4-8 carbon atoms, most preferably with 6 carbon atoms, wherein preferably the at least one hydrophobic acrylate building block is selected as 2-ethylhexyl acrylate.
  • the at least one monomeric hydrophobic building block in (HO RT) can further be preferably a saturated branched, cyclic and/or linear alkyl vinyl ester, wherein the alkyl chain is a saturated branched, cyclic or linear alkyl group with 5-20 carbon atoms, preferably with 4-17 carbon atoms, most preferably with 7-12 carbon atoms, wherein preferably the at least one hydrophobic vinylester monomer is selected as vinylneodecanoat.
  • the at least one monomeric hydrophilic building block in (HO RT) is preferably selected from a hydrophilic acrylate and/or methacrylate, preferably as a hydroxyalkyl acrylate and/or hydroxyalkyl methacrylate, wherein the alkyl chain is a saturated branched, cyclic or linear alkyl group with 1-5 carbon atoms, preferably with 2-4 carbon atoms, wherein preferably the hydrophilic acrylate monomer is selected from the group consisting of: 2- hydroxyethyl acrylate, 2 -hydroxy ethyl methacrylate or a mixture thereof. Most preferably the hydrophilic acrylate is selected as 2 -hydroxy ethyl methacrylate.
  • HO_RT is based on or formed exclusively from
  • bifunctional reactive monomeric acrylate or acrylamide building block selected as glycidyl methacrylate alone or N-methylol methacrylamide alone
  • the mass proportion of the sum of the monomeric hydrophobic building blocks to the bifunctional reactive monomeric acrylate or acrylamide building block can be in the range of 3:1 to 15:1, preferably 5:1 - 10:1, and/or the mass proportion of the two monomeric hydrophobic building blocks is in the range of 2: 1 - 1 :2, preferably 1.2:1 - 1 :1.2.
  • the weight ratio of the sum of the at least one monomeric hydrophobic building blocks and the sum of the at least one bifunctional monomeric acrylate or acrylamide building blocks in (HO R.T) can be in the range of 15: 1 - 2:1, preferably in the range of 10:1 - 5:1.
  • the block (HO) can be based on or formed exclusively from at least one hydrophobic acrylate and/or hydrophobic vinylester monomer.
  • HO can be based on or formed exclusively from at least two different hydrophobic (meth)acrylate and/or hydrophobic vinylester monomers, and wherein further preferably the two different hydrophobic (meth)acrylate and/or hydrophobic vinylester monomers differ in their hydrophobicity.
  • (HO) can be based on or formed exclusively from at least one hydrophobic (meth)acrylate and/or hydrophobic vinylester monomer as well as at least one hydrophilic (meth)acrylate and/or hydrophilic vinylester monomer.
  • HO can also be based on or formed exclusively from at least two different hydrophobic (meth)acrylate and/or hydrophobic vinylester monomers, preferably differing in their hydrophobicity, as well as at least one hydrophilic (meth)acrylate and/or hydrophilic vinylester monomer.
  • the at least one hydrophobic acrylate monomer in (HO) is preferably selected from alkyl acrylate and alkyl methacrylate monomers, wherein the alkyl chain is a saturated branched or linear alkyl group with 3-12 carbon atoms, preferably with 4-8 carbon atoms, most preferably with 6 carbon atoms, wherein preferably the at least one hydrophobic acrylate building block is selected as 2-ethylhexyl acrylate.
  • the at least one hydrophobic vinylester monomer in (HO) is preferably a saturated branched, cyclic and/or linear alkyl vinyl ester, wherein the alkyl chain is a saturated branched, cyclic or linear alkyl group with 5-20 carbon atoms, preferably with 4-17 carbon atoms, most preferably with 7-12 carbon atoms, wherein preferably the at least one hydrophobic vinylester monomer is selected as vinylneodecanoat.
  • the at least one hydrophilic (meth)acrylate monomer in (HO) is preferably selected hydroxyalkyl acrylate and/or hydroxyalkyl methacrylate, wherein the alkyl chain is a saturated branched, cyclic or linear alkyl group with 1 -5 carbon atoms, preferably with 2-4 carbon atoms, wherein preferably the hydrophilic acrylate monomer is selected from the group consisting of: 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate or a mixture thereof, wherein preferably the hydrophilic acrylate is selected as 2-hydroxyethyl methacrylate.
  • the average number of monomeric building blocks within (HO) can be in the range of 2- 20, preferably in the range of 3-15.
  • (HO) is most preferably based on or formed exclusively from
  • mass proportion of the sum of the monomeric hydrophobic building blocks to the hydrophilic acrylate and/or hydrophilic vinylester monomer can be in the range of 5:1 to 1 :1, preferably 3:1 - 2:1, and/or the mass proportion of the two monomeric hydrophobic building blocks is in the range of 2: 1 - 1 :2, preferably 1.2: 1 - 1 : 1.2.
  • the block (HI) is preferably formed from at least one hydrophilic (meth)acrylate monomer selected to be hydroxyalkyl acrylate and/or hydroxyalkyl methacrylate, wherein the alkyl chain is a saturated branched, cyclic or linear alkyl group with 1-5 carbon atoms, preferably with 2-4 carbon atoms.
  • the hydrophilic (meth)acrylate monomer is selected from the group consisting of: 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate or a mixture thereof, wherein preferably the hydrophilic acrylate is selected, preferably exclusively, as 2-hydroxyethyl methacrylate.
  • the average number of monomeric building blocks within (HI) is preferably in the range of 2-20, more preferably in the range of 3-15.
  • the weight proportion of the blocks in the block-copolymer (I) is, according to a preferred embodiment, selected to be as follows
  • (HO) / (HI) is in the range of 1 :5 - 1 : 1 , preferably in the range of 1 :3 - 1 : 1.5, or in the range of 1 :2;
  • (HO) / (HO_RT) is in the range of 1 :2 - 2:1 , preferably in the range of 1.5:1 - 1 :1.5, or in the range of 1 : 1.
  • a particularly preferred embodiment of (I) is as follows:
  • (HO) is based exclusively on vinylneodecanoat, 2-ethylhexyl acrylate and 2-hydroxyethyl methacrylate, preferably in a weight proportion of in the range of 1 : 1 : 1 ;
  • HO RT is based exclusively on vinylneodecanoat, 2-ethylhexyl acrylate and either glycidyl methacrylate alone or N-methylol methacrylamide alone,
  • the block-copolymer (I) can be and typically is present in the formulation as a core shell particle, the (HO) block forming an innermost core, the (HI) block forming an intermediate, preferably water swellable shell and the (HO_RT) block forming an outer reactive shell.
  • the block-copolymer (I) can be present in the formulation as an emulsion or dispersion in water and at least partially embedded in a micellar structure, wherein the micellar structure is preferably formed by at least one surfactant, preferably formed by at least one of an alkylbenzene sulfonic acid, preferably dodecylbenzene sulfonic acid and/or an polyoxyethylene (EO) and/or polyoxypropylene (PO) non-ionic surfactant, preferably ethoxylated fatty systems such as alcohol iso-tridecyl alcohol 6 (EO) (which is an alpha- tridecyl-omega-hydroxy-poly(oxy-l,2-ethanediyl) with on average 6 oxy-l,2-ethanediyl blocks).
  • EO alcohol iso-tridecyl alcohol 6
  • the present invention relates to a use of a formulation as detailed above or a treatment liquor comprising a formulation as detailed above for the coating of fibers and/or textiles, wherein preferably the fibers and/or textiles are based on cotton, hemp, flax, lyocell, rayon, jute, wool, polyester, polyamide, modacrylic, olefinic, acrylic, or a mixture and/or blend thereof, preferably cellulose based fibres such as cotton, in particular to impart a soil release effect.
  • a softener formulation and/or cationic fixer formulation preferably based on quaternary polyamine systems.
  • the invention relates to a method for treatment of fibers and/or textiles, wherein preferably the fibers and/or textiles are based on cotton, hemp, flax, lyocell, rayon, jute, wool, polyester, polyamide, modacrylic, olefinic, acrylic, or a mixture and/or blend thereof, preferably cellulose based fibres such as cotton, with a formulation according to any of claims 1-11, or with a treatment liquor comprising a formulation as given above, in particular to impart a soil release effect.
  • the fibers and/or textiles can be treated by the formulation or using a treatment liquor based on such a formulation during a time span of 10 to 40 minutes, preferably in the range of 15 to 30 minutes, at a temperature in the range of 20 to 60 °C, preferably at a temperature in the range of 30 to 50 °C or by forced application.
  • the fibers and/or textiles are typically subjected to at least one of the following post-treatments after drying: compacting, calendaring, decatizing, raising, emerizing, condensation of crosslinkers or selfcrosslinking polymers.
  • Last but not least the invention relates to a fiber or textile treated with such a formulation or resulting from a method as given above, in particular garment, article of clothing, including underwear, outerwear, protective clothing, sports clothing, in particular based on cellulose fibres.
  • the invention relates to a method of making the block-copolymer (I) of the formulation as given above, wherein
  • a surfactant preferably formed by at least one of an alkylbenzene sulfonic acid, preferably dodecylbenzene sulfonic acid and/or an polyoxyethylene (EO) and/or polyoxypropylene (PO) non-ionic surfactant, preferably ethoxylated or propoxylated fatty alcohol systems, including iso-tridecyl alcohol 6 (EO) at least one hydrophobic monomer for the formation of the (HO) block is polymerized, in a second subsequent step, if need be after addition of catalyst and/or activator, in an emulsion polymerization, the monomer forming the (HI) block, in one or several repeated steps, is added to form a structure of the type:
  • EO polyoxyethylene
  • PO polyoxypropylene
  • the aim is to synthesize a soil release polymer having good results especially with hydrophobic (oily) stains on cellulose fibers. This is achieved by a three-step sequential copolymerization.
  • Iso-tridecyl alcohol with 6EO e.g. Lutensol TO 6, BASF SE
  • Bruggolite FF6 M (Briiggemann KG), reducing agent, containing ascorbic acid (AA), sodium formaldehyde sulfoxylate (SFS) along with t-butyl hydroperoxide (TBHP), 10% solution in water
  • VeoVa 10 Vinyl ester of versatic acid, neodecanoic acid vinyl ester, available from Hexion
  • the emulsion becomes turbid.
  • the reaction enthalpy keeps the temperature from dropping too fast, but does not lead to a temperature increase.
  • GMA Glycidyl methacrylate
  • the emulsion becomes turbid.
  • the reaction enthalpy keeps the temperature front dropping too fast, but does not lead to a temperature increase.
  • the fabric is dried for 2 minutes at 120°C and cured for 5 minutes at 150°C
  • a 100% cotton interlock is padded with
  • Liquor add-on (pick-up) of 80% Liquor add-on (pick-up) of 80%.
  • the fabric is dried for 2 minutes at 120°C and cured for 1 minute at 170°C
  • a 100% cotton shirting fabric is padded with
  • the fabric is dried for 2 minutes at l20°C and cured for 5 minutes at l50°C
  • a 100% cotton interlock is padded with
  • Liquor add-on (pick-up) of 80% Liquor add-on (pick-up) of 80%.
  • the fabric is dried for 2 minutes at l20°C and cured for 1 minute at 170°C
  • a 100% cotton shirting fabric is padded with
  • the fabric is dried for 2 minutes at l20°C and cured for 5 minutes at l50°C
  • the fabric is dried for 2 minutes at 120°C and cured for 5 minutes at 150°C
  • a 100% cotton interlock is padded with
  • Liquor add-on (pick-up) of 80% Liquor add-on (pick-up) of 80%.
  • the fabric is dried for 2 minutes at 120°C and cured for 1 minute at 170°C
  • a 100% cotton shirting fabric is padded with
  • the fabric is dried for 2 minutes at l20°C and cured for 5 minutes at l50°C
  • the fabrics finished with the application recipes 1 to 9 were divided into 4 parts, one part was left as is, one part subjected to 1 domestic laundry operation ISO 6330 4N and tumble dried, one part subjected to 10 domestic laundry operations ISO 6330 4N and tumble dried, and one part subjected to 30 domestic laundry operations ISO 6330 4N and tumble dried.
  • the textile samples were tested for soil-release property by carrying out the AATCC (American Association of Textile Chemists and Colorists) Test Method 130-2010; i.e. they were stained with corn (maize) oil, the stain squeezed into the textile by placing a defined weight for a defined time onto it, and then the stained textile swatches were subjected to the washing process III of the said test method. After air drying the samples were evaluated using the scale of the AATCC TM 130-2010.
  • AATCC American Association of Textile Chemists and Colorists
  • Stain release ratings were determined by placing the stained, washed, and dried fabric flat in the center of a non-glare blacktop table with one edge of the table touching a Stain Release Replica (available from the AATCC). The fabric was viewed from a distance of ca.. 75 cm and the residual stain was compared to the Stain Release Replica to the nearest 0.5 rating. Ratings are given from 1 (minimum) to 5 (maximum). In the United States, a normally accepted level of stain release is a rating of 3.

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

Abstract

La présente invention concerne une formulation de traitement textile pouvant conférer durablement des propriétés anti-taches à des fibres ou à des vêtements, en particulier à des fibres ou à des vêtements en coton ou à base de coton, ladite formulation contenant une quantité efficace d'un copolymère séquencé (I) ou d'un mélange correspondant. Le copolymère séquencé (I) comprend au moins une ou plusieurs séquences de la structure suivante ou est constitué de la structure suivante : (HO)-(HI)-(HO_RT) (I), dans laquelle (HO_RT) est une séquence de queue réactive hydrophobe, à base ou formée exclusivement d'au moins une séquence de construction monomère hydrophobe ainsi que d'au moins une séquence de construction monomère acrylate ou acrylamide réactive bifonctionnelle ; (HO) est une séquence hydrophobe, à base ou formée exclusivement d'au moins une séquence de construction monomère hydrophobe ; (HI) est une séquence hydrophile, à base ou formée exclusivement d'au moins une séquence de construction monomère acrylate hydrophile.
PCT/EP2018/083995 2017-12-13 2018-12-07 Formulations antisalissure pour applications textiles Ceased WO2019115392A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP17206990.8 2017-12-13
EP17206990 2017-12-13

Publications (1)

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WO2019115392A1 true WO2019115392A1 (fr) 2019-06-20

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1719359A1 (de) 1968-02-15 1970-10-29 Pfersee Chem Fab Verfahren zur Verbesserung der Soil-Release-Eigenschaften von Geweben
GB1473362A (en) 1973-08-01 1977-05-11 Daido Maruta Finishing Process for treating fibrous products
US5763022A (en) 1994-09-15 1998-06-09 Wacker-Chemie Gmbh Solvent-resistant textile binder
US20030114583A1 (en) * 2001-10-31 2003-06-19 Wacker Polymer Systems Gmbh & Co., Kg Hydrophobicized copolymers
WO2003054284A1 (fr) 2001-05-15 2003-07-03 E.I. Du Pont De Nemours And Company Materiau d'hydrofugation et d'oleofugation a durabilite elevee et a faible jaunissement destine a des textiles
US20030226211A1 (en) * 2002-03-08 2003-12-11 University Of Southern Mississipi Waterborne fabric and textile coating or treatment
US20060116495A1 (en) 2003-01-20 2006-06-01 Kurt Stark Silicone polymerisates

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1719359A1 (de) 1968-02-15 1970-10-29 Pfersee Chem Fab Verfahren zur Verbesserung der Soil-Release-Eigenschaften von Geweben
GB1473362A (en) 1973-08-01 1977-05-11 Daido Maruta Finishing Process for treating fibrous products
US5763022A (en) 1994-09-15 1998-06-09 Wacker-Chemie Gmbh Solvent-resistant textile binder
WO2003054284A1 (fr) 2001-05-15 2003-07-03 E.I. Du Pont De Nemours And Company Materiau d'hydrofugation et d'oleofugation a durabilite elevee et a faible jaunissement destine a des textiles
EP1399618A1 (fr) * 2001-05-15 2004-03-24 E.I. Du Pont De Nemours And Company Materiau d'hydrofugation et d'oleofugation a durabilite elevee et a faible jaunissement destine a des textiles
US20030114583A1 (en) * 2001-10-31 2003-06-19 Wacker Polymer Systems Gmbh & Co., Kg Hydrophobicized copolymers
US20030226211A1 (en) * 2002-03-08 2003-12-11 University Of Southern Mississipi Waterborne fabric and textile coating or treatment
US20060116495A1 (en) 2003-01-20 2006-06-01 Kurt Stark Silicone polymerisates

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