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WO2025075700A1 - Composition de copolymère de silicone-(méth) acrylate et formulation d'émulsion pour traitement de textiles - Google Patents

Composition de copolymère de silicone-(méth) acrylate et formulation d'émulsion pour traitement de textiles Download PDF

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Publication number
WO2025075700A1
WO2025075700A1 PCT/US2024/039475 US2024039475W WO2025075700A1 WO 2025075700 A1 WO2025075700 A1 WO 2025075700A1 US 2024039475 W US2024039475 W US 2024039475W WO 2025075700 A1 WO2025075700 A1 WO 2025075700A1
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group
alternatively
subscript
carbon atoms
surfactant
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PCT/US2024/039475
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Inventor
Matthew JELETIC
Michael TELGENHOFF
Barbara CRESSMAN
Yusei SAKURAI
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Dow Global Technologies LLC
Rohm and Haas Co
Dow Silicones Corp
Original Assignee
Dow Global Technologies LLC
Rohm and Haas Co
Dow Silicones Corp
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Publication of WO2025075700A1 publication Critical patent/WO2025075700A1/fr
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    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
    • C09D143/04—Homopolymers or copolymers of monomers containing silicon
    • 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
    • D06M13/152—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 having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • D06M15/244—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of 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
    • 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
    • D06M15/27—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of alkylpolyalkylene glycol esters of unsaturated carboxylic acids
    • 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
    • D06M15/333—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof of vinyl acetate; Polyvinylalcohol
    • 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
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
    • D06M15/3568—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing silicon
    • 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

  • a composition includes a silicone - (meth)acrylate copolymer, a manganese ion source, and a phenolic compound; and methods for preparation and use of said composition are provided.
  • the composition is useful in an emulsion formulation for treating textiles to provide the textiles with durable water repellency.
  • each D 2 is a divalent hydrocarbon group of 2 to 12 carbon atoms.
  • D 2 may have 2 to 10, alternatively 3 to 5, and alternatively 3 carbon atoms.
  • Each D 3 and each D is independently a divalent hydrocarbon group of 1 to 12 carbon atoms.
  • each D 3 and each D may be an alkylene group; alternatively ethylene.
  • D 4 and D 1 are each independently an alkylene group of 2 to 4 carbon atoms or a divalent alkylarylene group.
  • each R 8 is a crosslinkable group.
  • Each R 8 may be independently selected from the group consisting of hydroxy, amino, epoxy, ureido, and acetoxy.
  • each R 8 may be independently selected from the group consisting of hydroxy and ureido, and alternatively each R 8 may be hydroxy.
  • each R 5 is an oxygen atom.
  • Each R 6 is selected from the group consisting of -OH and alkoxy. Alternatively, the alkoxy group for R 6 may be -OCH3.
  • each R 9 is a monovalent hydrocarbon group, which is free of aliphatic unsaturation and which may be linear, branched, or cyclic (i.e., monocyclic or polycyclic), or combinations thereof.
  • R 9 may be an alkyl group or an aryl group, which may be monocyclic or polycyclic, and which may optionally have linear or branched groups.
  • suitable alkyl groups for R 9 may include methyl, t-amyl, butyl (including t-butyl), cyclohexyl, iso-decyl, isobornyl, and 2-ethylhexyl.
  • suitable aryl groups include phenyl, naphthyl, anthracyl, and benzyl.
  • R 10 may be a halide, an acetate, or a monovalent hydrocarbon group, as described above for R 9 .
  • the halide may be bromide (Br), chloride (Cl), fluoride (F) or iodide (I); alternatively Br, Cl or F; alternatively Br or Cl; and alternatively Cl.
  • Subscript zl may be 0.
  • subscript zl may be at least 0.5, alternatively at least 1, and alternatively at least 2; while at the same time, subscript zl may be up to 18, alternatively up to 15, alternatively up to 10, alternatively up to 8, and alternatively up to 5.
  • subscript zl may be 0 to 18, alternatively > 0 to 18, alternatively 0.5 to 7, alternatively 1 to 6, and alternatively 2 to 5.
  • Subscript z2 may be 0.
  • subscript z2 may be at least 0.5, alternatively at least 1 , and alternatively at least 2; while at the same time, subscript z2 may be up to 8, alternatively up to 7, alternatively up to 6, alternatively up to 5, and alternatively up to 4.
  • subscript z2 may be 0 to 8, alternatively > 0 to 8, alternatively 0.5 to 7, alternatively 1 to 6, and alternatively 2 to 5.
  • the copolymer may be prepared by any convenient means such as that disclosed in PCT Patent Application Publication W02023/019044 to Jeletic et al. by using the manganese ion source and the phenolic compound described herein as inhibitors, instead of the inhibitor described therein.
  • the copolymer may be prepared as described in U.S. Patent 10,047,199 to limura et al. by varying appropriate starting materials and their amounts and by including the manganese ion source and the phenolic compound described herein.
  • PCT Patent Application Publication W02023/019044 and U.S. Patent 10,047,199 are hereby incorporated by reference.
  • the starting materials used in the process to prepare the composition may optionally further comprise (H) a chain transfer agent; (J) an additional non- crystallizable monomer that is distinct from each of (A), (B) and (C); and a combination of both (H) and (J).
  • step (1) copolymerizing starting materials (A), (B), (C), (F), and when present (H) and/or (J), in the presence of the (K) manganese ion source and (L) the phenolic compound, may be performed in a process such as that disclosed in U.S. Patent 10,047,199 to limura et al. by varying appropriate starting materials and their amounts.
  • the resulting reaction product which comprises the copolymer, (K) the manganese ion source, and (L) the phenolic compound, may be solvent borne. When solvent is present, all or a portion of the solvent may be removed by any convenient means, such as by stripping or distillation with optionally with heat and/or optionally reduced pressure.
  • the emulsion polymerization process described above may comprise forming an emulsion comprising starting materials (A), (B), (C), (D), (E), (K), and (L) (and optionally (H) and/or (J)), and thereafter adding (F) the initiator and copolymerizing.
  • starting materials (K) and (L) may inhibit formation of acrylic radicals that can impact the formation of the copolymer during copolymerization in step (1).
  • Starting material (A) used to prepare the copolymer is a crystallizablc monomer of formula ( 2 are as described above.
  • Examples of crystallizablc monomers for starting material (A) include stcaryl (mcth)acrylatc, eicosyl (meth)acrylate, behenyl (meth)acrylate, and combinations thereof.
  • R 2 is hydrogen
  • starting material (A) may be an acrylate selected from stearyl acrylate, eicosyl acrylate, behenyl acrylate, and combinations thereof.
  • starting material (A) may be stearyl acrylate.
  • Crystallizable monomers suitable for starting material (A) are commercially available, e.g., from Millipore Sigma of St. Louis, Missouri, USA and from BASF SE of Ludwigshafen, Germany. Crystallizable means that the stalling monomer has a melting point ) > 25 °C ⁇ 5 °C.
  • starting material (B) may have a formula selected from the group consisting of: 4 are as described above.
  • Stalling material (D) is a surfactant.
  • the surfactant used in copolymerizing in step (1) of the process for making the aqueous emulsion is not specifically restricted and may be selected from the group consisting of anionic surfactants, amphoteric surfactants, cationic surfactants, nonionic surfactants, and combinations of two or more thereof.
  • the anionic surfactants include (i) sulfonic acids and their salt derivatives, including alkyl, aralkyl, alkyl naphthalene, alkyl diphenyl ether sulfonic acids, and their salts, having at least 6 carbon atoms in the alkyl substituent, such as dodecyl benzene sulfonic acid, and its sodium salt or its amine salt; (ii) alkyl sulfates having at least 6 carbon atoms in the alkyl substituent, such as sodium lauryl sulfate; (iii) the sulfate esters of polyoxyethylene monoalkyl ethers; (iv) long chain carboxylic acid surfactants, such as lauric acid, steric acid, oleic acid, and their alkali metal and amine salts.
  • sulfonic acids and their salt derivatives including alkyl, aralkyl, alkyl naphthalene, alkyl
  • compositions of the latter type such as dodecyl benzene sulfonic acid, although a catalyst as noted above, can also function as the anionic surfactant when neutralized.
  • suitable surfactants include sodium alkyl sulfonate such as HOSTAPURTM SAS-30, and triethanolamine dodecyl benzene sulfonate, such as BIO-SOFTTM N 300.
  • Suitable amphoteric surfactants include amino acid surfactants, betaines (e.g., lauryl betaine, bis-(2-hydroxyethyl) tallow betaine, cocamidopropylbetaine, N-alkylamidobetaines, and derivatives thereof), proteins and derivatives thereof, glycinates (glycine derivatives, such as cocamphoglycinate, cocamphocarboxy-glycinates, and cocamphodipropionate), sultaines (e.g., cocamidopropylhydroxysultaine and lauryl sultaine), alkyl aminopropionates, alkyl polyaminocarboxylates and alkylamphoacetates, lecithin and hydrogenated lecithin, and combinations thereof.
  • surfactants are commercially available from various suppliers under different tradenames. For example, REWOTERICTM AM TEG is produced by Evonik of Essen, Germany; AMPHOSOLTM CG is available from Step
  • Cationic surfactants useful herein include compounds containing quaternary ammonium hydrophilic moieties in the molecule which are positively charged, such as quaternary ammonium salts, which may be represented by formula (D-2-1): R 12 R 13 R 14 R 15 N + X’" where R 12 to R 15 are alkyl groups containing 1-30 carbon atoms, or alkyl groups derived from tallow, coconut oil, or soy; and X’ is a halogen, e.g., chlorine or bromine.
  • quaternary ammonium salts which may be represented by formula (D-2-1): R 12 R 13 R 14 R 15 N + X’" where R 12 to R 15 are alkyl groups containing 1-30 carbon atoms, or alkyl groups derived from tallow, coconut oil, or soy; and X’ is a halogen, e.g., chlorine or bromine.
  • Representative quaternary ammonium halide salts are dodecyltrimethyl ammonium chloride/lauryltrimethyl ammonium chloride (LTAC), cetyltrimethyl ammonium chloride (CTAC), hexadeclyltrimethyl ammonium chloride, didodecyldimethyl ammonium bromide, dihexadecyldimethyl ammonium chloride, dihexadecyldimethyl ammonium bromide, dioctadecyldimethyl ammonium chloride, dieicosyldimethyl ammonium chloride, and didocosyldimethyl ammonium chloride.
  • LTAC dodecyltrimethyl ammonium chloride/lauryltrimethyl ammonium chloride
  • CTAC cetyltrimethyl ammonium chloride
  • hexadeclyltrimethyl ammonium chloride didodecyldimethyl ammonium bromide
  • the surfactant used in copolymerizing in step (1) may be (D-3) a nonionic surfactant.
  • suitable nonionic surfactants which can be used include polyoxyalkylene copolymers, such as polyoxyethylene alkyl ethers, polyoxyethylene alkylphenol ethers, alkyl glycosides (e.g., alkylglucosides), polyoxyethylene fatty acid esters, polyoxyethylene lauryl ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitan monooleates, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, polyethylene glycol (such as polyethylene glycol having 23 cthylcnc-oxidc units), polypropylene glycol, diethylene glycol, ethoxylated trimethylnonanols, tristyrylphenol ethers (TSP’s), distyryl phenol
  • alkyl-oxo alcohol polyglycol ethers such as GENAPOLTM UD 050, and GENAPOLTM UDI 10
  • alkyl polyethylene glycol ether based on ClO-Guerbet alcohol and ethylene oxide such as LUTENSOLTM XP 79
  • other alcohol ethoxylates for example, C11-15 alkyl alcohol ethoxylate with tradename ECOSURFTM EH, such as ECOSURFTM EH-40, from TDCC.
  • TSPs and DSP’s are commercially available from Stepan.
  • Suitable nonionic surfactants also include poly(oxyethylene)-poly(oxypropylene)- poly(oxyethylene) tri-block copolymers.
  • Poly(oxyethylene)-poly(oxypropylene)- poly(oxyethylene) tri-block copolymers are also commonly known as Poloxamers. They are nonionic triblock copolymers composed of a central hydrophobic chain of polyoxypropylene (polypropylene oxide)) flanked by two hydrophilic chains of polyoxyethylene (poly(ethylene oxide)).
  • Poly(oxyethylene)-poly(oxypropylene)-poly(oxyethylene) tri-block copolymers are commercially available from BASF of Florham Park, New Jersey, USA, and are sold under the tradename PLURONICTM, such as PLURONICTM L61, L62, L64, L81, P84.
  • the amount of nonionic surfactant may be at least 0.1%, alternatively at least 0.2%, alternatively at least 0.3%, alternatively at least 0.4%, alternatively at least 0.5%, alternatively at least 1%; while at the same time the amount of nonionic surfactant may be up to 10%, alternatively up to 5%, alternatively up to 4%, alternatively up to 3%, alternatively up to 2%, alternatively up to 1%, on the same basis.
  • the amount of nonionic surfactant may be 0.2% to 4%, alternatively 0.3% to 3%, alternatively 0.4 to 2.5%, and alternatively 1% to 2%; on the same basis.
  • Starling material (E) is water.
  • the water is not generally limited, for example, the water may be processed or unprocessed. Examples of processes that may be used for purifying the water include distilling, filtering, deionizing, and combinations of two or more thereof, such that the water may be deionized, distilled, and/or filtered. Alternatively, the water may be unprocessed (e.g. may be tap water, i.e., provided by a municipal water system or well water, used without further purification). The amount of water is sufficient to form an aqueous emulsion for copolymerizing in step (1) of the process described above.
  • the peroxide compound may be a peroxide or a hydroperoxide, such as t-butylperoctoate, t-butyl perbenzoate, dicumyl peroxide, di-t-butyl peroxide, t-butyl hydroperoxide, cumene hydroperoxide, di-t-amyl peroxide and combinations of two or more thereof.
  • di-peroxide initiators may be used alone or in combination with other initiators.
  • the additional monomer may be present in an amount of at least 0.5%, alternatively at least 1%, and alternatively at least 2%; while at the same time the additional monomer may be present in an amount up to 18%, alternatively up to 15%, alternatively up to 10%, alternatively up to 8%, and alternatively up to 5%, on the same basis.
  • the amount of (H) the additional monomer may be > 0 to 18%, alternatively 0.5% to 7%, alternatively 1% to 6%, and alternatively 2% to 5%, on the same basis.
  • Starting material (J) is an optional reactive surfactant that may be used to facilitate emulsion copolymerization, and that may react to form part of the copolymer.
  • the reactive surfactant may have formula:
  • a reactive surfactant of formula subscript vl has a value sufficient to give the reactive surfactant a number average molecular weight of 300 g/mol to 950 g/mol is commercially available from Sigma- Aldrich, Inc. of St. Louis, Missouri, USA.
  • the reactive surfactant is optional and may be added in an amount of 0 to 5 weight % based on combined weights of starting materials (A), (B), and (C), and when present (H), and (J).
  • Reactive surfactants are commercially available, e.g., from Ethox.
  • the reactive surfactant may be added in an amount of > 0 to 2 weight % on the same basis.
  • the amount of the manganese ion source may be > 0 ppm, alternatively at least 0.5 ppm, alternatively at least 1 ppm, alternatively at least 1 .5; while at the same time, the amount of manganese ion source may be up to 10 ppm, alternatively up to 5 ppm, alternatively up to 4 ppm, and alternatively up to 3 ppm, and alternatively up to 2 ppm, based on combined weights of all starting materials in the emulsion formulation for treating the textile.
  • Mixing under shear may be performed by any convenient means for forming an aqueous emulsion formulation, such as sonication and with subsequent microfluidization.
  • Equipment for mixing under shear such as sonicators, homogenizers, microfluidizers, and speedmixers are known in the art and are commercially available.
  • each D 5 is an independently selected alkylene oxide group of 2 or more carbon atoms.
  • R 19 may be, for example, 2-ethylhexyl, lauryl, or other alkyl group of 8 to 15 carbon atoms.
  • subscript n may be 23 to 40, alternatively 23 to 30.
  • each D 5 may be independently selected from the group consisting of ethylene oxide and propylene oxide.
  • each D 5 may be ethylene oxide.
  • This process for preparing the emulsion formulation suitable for treating the textile may optionally further comprise adding a further additional starting material.
  • the further additional starting material may be selected from the group consisting of (V) a wax, (VI) a biocide, (VII) additional water (which may be the same as starting material (E)), (VIII) a flame retardant, (IX) a wrinkle reducing agent, (X) an antistatic agent, (XI) a penetrating agent and a combination of two or more of (V) to (XI).
  • the aqueous emulsion prepared in the process comprising step (1), described above may be used to prepare the emulsion formulation suitable for treating the textile.
  • the process described above comprising step (1) further comprises step (2): adding starling material (IV), the water dispersible crosslinker, to the aqueous emulsion.
  • This process for preparing the emulsion formulation suitable for treating the textile may optionally further comprise, after step (1), adding the further additional starting material.
  • crosslinker (IV) examples include U.S. Patent Application 2017/0204558 to Knaup; U.S. Patent 9,777,105 to Hamajima et al., beginning at col. 11, line 54, which are hereby incorporated by reference for the purpose of describing suitable crosslinkers.
  • the exact amount of crosslinker (IV) depends on various factors including the type and amount of (I) silicone - (meth)acrylate copolymer and the textile to be treated, however, the weight of the crosslinker (IV) may 0.25% to 3.75% on fabric weight, alternatively 0.25% to 1%, and alternatively 0.25% to 0.5%, on the same basis.
  • Starting material (V) is a wax, which may optionally be added to provide improved water repellency or softness to the textile to which the emulsion formulation will be applied.
  • the amount of wax will vary depending on factors including the type of wax selected, the benefit desired, and the fabric to be treated with the emulsion formulation. However, the amount of wax may be 0 to 75%, alternatively 0 to 50%, alternatively 25% to 50% based on weight of (I) the silicone - (meth)acrylate copolymer. Alternatively, when used, the amount of wax may be > 0%, alternatively at least 10%, and alternatively at least 25%, while at the same time the amount of wax may be up to 75%, alternatively up to 50% on the same basis.
  • suitable waxes include paraffin waxes (e.g., n-paraffins, iso-paraffins, and/or cycloparaffins), silicone waxes such as silicone wax with long chain alkyl groups (e.g., alkyl methyl silicone wax) and/or amino-silicone wax, and a combination of two or more thereof.
  • Suitable waxes are disclosed, for example, in U.S. Patent Application 2017/0204558 to Knaup and U.S. Patent 10,844,151 to Probst, et al.
  • Waxes may be delivered as water-based dispersions, for example Michelman wax 743 and others from Michelman of Cincinnati, Ohio, U.S.A.
  • Other waxes are also commercially available, for example, from Sasol Wax of Hamburg, Germany, and silicone waxes, such as DOWSILTM AMS-C30, are available from Dow Silicones Corporation of Midland, Michigan, U.S.A.
  • the Bundesmann test may be carried out using the ISO 9865 method.
  • An SDL Atlas M230 Bundesmann test apparatus may be used to collect face rating data after 0, 1, 10, and 20 washes. The instrument may be calibrated so that each cup collected between 190 and 210mL after 150s. Face Ratings may be assigned based on the images in the ISO 9865 method using half increments as intermediate assignments. Face Ratings may be repeated and reported as averages. A passing value may be > 4.5 to 5.
  • any ranges and subranges relied upon in describing the present invention independently and collectively fall within the scope of the appended claims, and are understood to describe and contemplate all ranges including whole and/or fractional values therein, even if such values are not expressly written herein.
  • One of skill in the art readily recognizes that the enumerated ranges and subranges sufficiently describe and enable various embodiments of the present invention, and such ranges and subranges may be further delineated into relevant halves, thirds, quarters, fifths, and any other subrange subsumed within the range.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Une composition comprend un copolymère de silicone-(méth)acrylate, une source d'ions manganèse et un composé phénolique. La composition peut être utilisée avec des matériaux de départ supplémentaires comprenant un tensioactif, de l'eau et un agent de réticulation dispersible dans l'eau dans une formulation d'émulsion. La formulation d'émulsion peut être utilisée pour traiter un textile. L'invention concerne également des procédés de préparation de la composition et de la formulation d'émulsion.
PCT/US2024/039475 2023-10-05 2024-07-25 Composition de copolymère de silicone-(méth) acrylate et formulation d'émulsion pour traitement de textiles Pending WO2025075700A1 (fr)

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