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WO2025144523A1 - Utilisation de copolymères d'ester d'aminosiloxane pour le traitement de textiles - Google Patents

Utilisation de copolymères d'ester d'aminosiloxane pour le traitement de textiles Download PDF

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Publication number
WO2025144523A1
WO2025144523A1 PCT/US2024/056571 US2024056571W WO2025144523A1 WO 2025144523 A1 WO2025144523 A1 WO 2025144523A1 US 2024056571 W US2024056571 W US 2024056571W WO 2025144523 A1 WO2025144523 A1 WO 2025144523A1
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WO
WIPO (PCT)
Prior art keywords
group
emulsion
textile
alternatively
aminosiloxane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2024/056571
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English (en)
Inventor
Brian REKKEN
Anirudha BANERJEE
Tushar Shinde
Padmadas Nair
Brett Zimmerman
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.)
Dow Global Technologies LLC
Dow Silicones Corp
Original Assignee
Dow Global Technologies LLC
Dow Silicones Corp
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Publication date
Application filed by Dow Global Technologies LLC, Dow Silicones Corp filed Critical Dow Global Technologies LLC
Publication of WO2025144523A1 publication Critical patent/WO2025144523A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino 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
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences

Definitions

  • US Patent 8013097 discloses, “a process to prepare an amine terminal silicone polyether block copolymer comprising: I) reacting; A) a polyoxyalkylene having an unsaturated hydrocarbon group at each molecular terminal B) a SiH terminated organopolysiloxane, C) a hydrosilylation catalyst, D) an optional solvent, . . .
  • a process for treating a textile comprises: i) applying an emulsion comprising an aminosiloxane ester copolymer to the textile, and ii) drying the textile.
  • the process improves hydrophilicity of the textile.
  • the alkyl group for R 1 may be selected from the group consisting of methyl and ethyl, alternatively methyl.
  • Suitable alkenyl groups for R 1 include vinyl, allyl and hexenyl; alternatively vinyl or allyl; and alternatively vinyl.
  • Suitable aryl groups for R 1 may include cyclopentadienyl, phenyl, naphthyl, and anthracenyl.
  • Suitable aralkyl groups for R 1 include tolyl, xylyl, benzyl, 1 -phenylethyl, and 2- phenylethyl.
  • the aryl group for R 1 may be phenyl.
  • Each R E is independently selected from the group consisting of a hydroxyl group and an amino-functional group of formula H N-R A -, where R A is a divalent hydrocarbon group. Alternatively, each R E may be hydroxyl. Alternatively, each R E may be the amino-functional group of formula H2N-R A -.
  • Each R A is an independently selected divalent hydrocarbon group of 1 to 12 carbon atoms, alternatively 2 to 12 carbon atoms, alternatively 2 to 5 carbon atoms, and alternatively 2 to 3 carbon atoms.
  • the divalent hydrocarbon groups for R A may be linear, branched, or cyclic, or combinations thereof.
  • Each R 2 is independently selected from the group consisting of hydrogen and methyl. Alternatively, each R 2 may be hydrogen.
  • Each R D is an independently selected divalent hydrocarbon group of 2 to 20 carbon atoms, alternatively 2 to 12 carbon atoms, alternatively 3 to 12 carbon atoms, alternatively 4 to 12 carbon atoms, alternatively 4 to 10 carbon atoms, alternatively 4 to 6 carbon atoms, alternatively 6 to 12 carbon atoms, and alternatively 6 to 10 carbon atoms.
  • the divalent hydrocarbon groups for R D may be linear, branched, cyclic, or combinations thereof.
  • Suitable divalent hydrocarbon groups for R D include alkylene groups, arylene groups, and combinations thereof.
  • Subscript a has a value such that 0 ⁇ a ⁇ 150.
  • subscript a may have a value of 2 to 150, alternatively 14 to 145, alternatively 14 to 143, alternatively 42 to 145, alternatively 42 to 143, alternatively 82 to 145, alternatively 82 to 143, and alternatively 42 to 84.
  • Subscript b has a value such that 1 ⁇ b ⁇ 100.
  • subscript b may have a value of 2 to 100, alternatively 2 to 20, alternatively 2 to 10, and alternatively 3 to 4.
  • the copolymer described above may have a number average molecular weight (Mn) of > 1 ,000 g/mole to 250,000 g/mole measured by GPC according to the test method described hereinbelow.
  • the copolymer may have a Mn of 4,000 g/mole to 250,000 g/mole, alternatively 4,000 g/mole to 100,000 g/mole, measured by GPC.
  • the copolymer described above may have a weight average molecular weight (Mw) of 2,000 g/mol to 400,000 g/mol.
  • Mw may be 10,000 g/mol to 390,000 g/mol; alternatively 12,000 g/mol to 200,000 g/mol; alternatively 15,000 g/mol to 185,000 g/mol; alternatively 19,000 g/mol to 175,000 g/mol; alternatively 20,000 g/mol to 100,000 g/mol; alternatively 21,000 g/mol to 80,000 g/mol; alternatively 22,000 g/mol to 75,000 g/mol; alternatively 25,000 g/mol to 65,000 g/mol; alternatively 30,000 g/mol to 60,000 g/mol; alternatively 35,000 g/mol to 55,000 g/mol; and alternatively 40,000 g/mol to 50,000 g/mol.
  • the copolymer described above has both amino- and acrylate- groups in its backbone.
  • the copolymer may have a molar ratio of amino/acrylate groups in its backbone of > 1/1, alternatively at least 1.05/1, alternatively at least 1.1/1, and alternatively at least 1.15/1; while at the same time the molar ratio may be up to 2/1, alternatively up to 1.5/1, and alternatively up to 1.3/1.
  • the copolymer may have a molar ratio of amino/acrylate groups in its backbone of 1/1 to 2/1, alternatively 1.05/1 to 2/1, alternatively 1.1/1 to 2/1, alternatively 1.1/1 to 1.5/1, and alternatively 1.15/1 to 1.3/1.
  • the emulsion may comprise: (I) a liquid continuous phase comprising water, and (II) a discontinuous phase dispersed in the liquid continuous phase, where the discontinuous phase comprises the aminosiloxane ester copolymer described above.
  • the amount of copolymer added to the emulsion can vary and is not limited. However, the amount typically may range from a weight ratio of copolymer/emulsion of 1 to 70%, alternatively 2 to 60%. Water, surfactant (and additional starting materials, if present) may constitute the balance of the emulsion to 100%.
  • the water is not generally limited, and may be utilized neat (i.e., absent any carrier vehicles/solvents), and/or pure (i.e., free from or substantially free from minerals and/or other impurities).
  • the water may be processed or unprocessed prior to making the emulsion described herein. 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.
  • 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 water may be purified before use to make the emulsion.
  • the water is used in addition to the aminosiloxane ester copolymer and the surfactant (and additional starting materials, if any) to a balance of 100 % of the emulsion.
  • the emulsion comprising (A) the aminosiloxane ester copolymer further comprises (B) a surfactant.
  • the surfactant may be anionic, cationic, nonionic, or amphoteric, or a combination of two or more thereof.
  • the amount of surfactant may be 2 % to 25%, alternatively 2% to 20%, based on combined weights of all starting materials in the emulsion.
  • the anionic surfactant may selected from alkali metal sulfosuccinates, sulfonated glyceryl esters of fatty acids, salts of sulfonated monovalent alcohol esters, amides of amino sulfonic acids, sulfonated products of fatty acids nitriles, sulfonated aromatic hydrocarbons, condensation products of naphthalene sulfonic acids with formaldehyde, sodium octahydroanthracene sulfonate, sodium lauryl sulfate, alkali metal alkyl sulfates, alkyl ether sulfates having at least 8 carbon atoms, alkyl aryl ether sulfates, alkylarylsulfonates having at least 8 carbon atoms, alkylbenzenesulfonic acids, salts of alkylbenzenesulfonic acids, sulfuric esters of polyoxyethylene alkyl
  • the cationic surfactant may be selected from dodecylamine acetate, octadecylamine acetate, acetates of the amines of tallow fatty acids, homologues of aromatic amines having fatty acids, fatty amides derived from aliphatic diamines, fatty amides derived from aliphatic diamines, fatty amides derived from disubstituted amines, derivatives of ethylene diamine, quaternary ammonium compounds, salts of quaternary ammonium compounds, alkyl trimethylammonium hydroxides, dialkyldimethylammonium hydroxides, coconut oil, methylpolyoxyethylene cocoammonium chloride, dipalmitoylethyl hydroxyethylammonium methosulfate, amide derivatives of amino alcohols, amine salts of long chain fatty acids, and combinations thereof.
  • Nonionic surfactants are commercially available, for example, alkylphenol alkoxylates are available under the tradename ECOSURFTM EH; secondary alcohol ethoxylates, nonylphenol ethoxylates, and ethylene oxide/propylene oxide copolymers are commercially available under the tradename TERGITOLTM; and specialty alkoxylates such as amine ethoxylates and octylphenol ethoxylates are available under the tradename TRITON TM, all from The Dow Chemical Company.
  • alkylphenol alkoxylates are available under the tradename ECOSURFTM EH
  • secondary alcohol ethoxylates, nonylphenol ethoxylates, and ethylene oxide/propylene oxide copolymers are commercially available under the tradename TERGITOLTM
  • specialty alkoxylates such as amine ethoxylates and octylphenol ethoxylates are available under the tradename TRITON TM, all from
  • nonionic surfactants include TERGITOLTM 15-S-5, also from The Dow Chemical Company, which has an HLB value of 10.5; Lutensol XP 50 with an HLB value of 10, Lutensol XP 79 (an alcohol ethoxylate), Lutensol XP 100 (an alcohol ethoxylate), and Lutensol XP 140 with an HLB value of 16, each of which is available from BASF.
  • the amount of surfactant in the emulsion may be, for example, 0.03% to 25%, alternatively 0.03% to 4% based on combined weights of all the starting materials in the emulsion described herein.
  • the surfactant may comprise an amphoteric surfactant.
  • Suitable amphoteric surfactants include betaines such as alkyl(C12-14)betaine, cocoamidopropylbetaine, cocoamidopropyldimethyl-hydroxysulphobetaine, dodecylbetaine, hexadecylbetaine, and tetradecylbetaine; sultaines such as cocamidopropylhydroxysultaine; lecithin; hydrogenated lecithin; cocoamphodiacetates; cocoiminodipropionate; and dodecyliminodipropionate.
  • the surfactant in the emulsion may be a nonionic surfactant.
  • the surfactant may be an organic surfactant.
  • the surfactant may be both organic and nonionic.
  • the emulsion may be formed as a water-in-oil emulsion (w/o), which contains a water- in-oil surfactant, (which may subsequently be inverted by addition of more water).
  • the water- in-oil surfactant may be nonionic and may be selected from polyoxyalkylene-substituted silicones, silicone alkanolamides, silicone esters and silicone glycosides, as described above.
  • the emulsion is an oil-in-water (o/w) emulsion, it may include nonionic surfactants known in the art to prepare o/w emulsions.
  • Suitable nonionic surfactants for this embodiment are exemplified by the polyoxyethylene alkyl ethers, polyoxyethylene alkylphenol ethers, polyoxyethylene lauryl ethers, polyoxyethylene sorbitan monooleates, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, polyethylene glycol, polypropylene glycol, diethylene glycol, ethoxylated trimethylnonanols, and polyoxyalkylene glycol modified polysiloxane surfactants, as described above.
  • the amino-functional polydiorganosiloxane produced as described herein may comprise unit formula: (R 4 3SiOi/2)a(R 4 2SiO2/2)h(R 8 R 4 SiO2/2)c(R 8 R 4 2SiOi/2)d, where each R 4 is independently selected from a monovalent hydrocarbon group and a monovalent halogenated hydrocarbon group; each R 8 is independently selected from an endblocking group and an amino-functional group, with the proviso that at least one R 8 per molecule is the aminofunctional group; and subscripts a, b, c, and d represent average numbers of each unit in the unit formula.
  • the monovalent hydrocarbon group for R 4 may be as described above for R 1 , e.g., alkyl, alkenyl, aryl, and combinations thereof (such as aralkyl and aralkenyl).
  • halogenated hydrocarbon group means a hydrocarbon where one or more hydrogen atoms bonded to a carbon atom have been formally replaced with a halogen atom.
  • Monovalent halogenated hydrocarbon groups include haloalkyl groups, halogenated aryl groups, and haloalkenyl groups.
  • Haloalkyl groups include fluorinated alkyl groups such as trifluoromethyl (CF3), fluoromethyl, trifluoroethyl, 2-fluoropropyl, 3, 3, 3 -trifluoropropyl, 4,4,4- trifluorobutyl, 4,4,4,3,3-pentafluorobutyl, 5,5,5,4,4,3,3-heptafluoropentyl, 6, 6, 6, 5, 5, 4, 4,3,3- nonafluorohexyl, 8,8,8,7,7-pentafluorooctyl, 2,2-difluorocyclopropyl, 2,3-difluorocyclobutyl, 3,4-difluorocyclohexyl, and 3,4-difluoro-5-methylcycloheptyl; and chlorinated alkyl groups such as chloromethyl, 3-chloropropyl 2,2-dichlorocyclopropyl, 2,3-dichlorocyclopentyl.
  • the amount of co-solvent in the emulsion depends on various factors including the content of aminosiloxane ester copolymer in the emulsion, however, the amount of co-solvent may be 0 to 10%, alternatively > 0, alternatively at least 1%, based on combined weights of all starting materials in the emulsion; while at the same time the amount of co-solvent may be up to 10%, alternatively up to 8%, and alternatively up to 5%, on the same basis.
  • the acid compound may optionally be added to the emulsion for adjusting pH.
  • Suitable acids include acetic acid, formic acid, propionic acid, and combinations thereof.
  • Suitable acids for adjusting pH are disclosed, for example, in US Patent 6180117.
  • starting materials for use in the emulsion described above there may be overlap between types of starting materials because certain starting materials described herein may have more than one function.
  • the additional starting materials are distinct from one another and from the aminosiloxane ester copolymer, the surfactant, and the water.
  • Illustrative examples of continuous mixers/compounders include extruders, such as single-screw, twin-screw, and multi-screw extruders, co-rotating extruders, such as those manufactured by Krupp Werner & Pfleiderer Corp (Ramsey, NJ), and Leistritz (NJ); twin-screw counterrotating extruders, two-stage extruders, twin-rotor continuous mixers, dynamic or static mixers or combinations of these equipment.
  • extruders such as single-screw, twin-screw, and multi-screw extruders
  • co-rotating extruders such as those manufactured by Krupp Werner & Pfleiderer Corp (Ramsey, NJ), and Leistritz (NJ)
  • twin-screw counterrotating extruders twin-stage extruders
  • twin-rotor continuous mixers dynamic or static mixers or combinations of these equipment.
  • the starting materials described above may be combined under any suitable conditions for forming an emulsion.
  • any acid compound may be added at the end of the method, i.e., once the desired dilution level is reached.
  • the optional additional starting material may be added by any convenient means.
  • Certain additional starting materials, such as the co-solvent may be emulsified with the aminosiloxane ester copolymer, for example, when the aminosiloxane ester copolymer is prepared with the co-solvent.
  • additional starting materials may be combined by mixing with the emulsion comprising the aminosiloxane ester copolymer after formation of the emulsion, e.g., when an amino- functional polydiorganosiloxane is used, the amino-functional polydiorganosiloxane may be emulsified, and the resulting emulsion may be mixed with an emulsion comprising the aminosiloxane ester copolymer, as described above.
  • 90% ⁇ 5% of the emulsion comprising the aminosiloxane ester copolymer and 10% ⁇ 5% of an aqueous emulsion comprising the amino-functional polydiorganosiloxanes, a surfactant, and water may be combined by mixing to form the emulsion to be used in the process for treating textiles.
  • the emulsion described above may be used in a process for treating textiles, e.g., fibers and/or fabrics.
  • the process comprises: i) applying the emulsion described above to a textile, and ii) drying the textile.
  • the emulsion may be applied to the textile by any convenient method.
  • the emulsion may be applied by padding, dipping, spraying or exhausting.
  • the emulsion may be applied to the textile during making the fiber or fabric, or later such as during laundering the textile.
  • the amount of emulsion applied to the textile depends on various factors including the type of textile and the amount of aminosiloxane ester copolymer in the emulsion.
  • the amount of the emulsion applied to the textile may be sufficient to provide 0.2 % to 15 % of the emulsion on the textile, based on dry weight of the textile, alternatively 0.2 % to 5 %, on the same basis.
  • the amount of the emulsion applied to the textile may be sufficient to deliver 0.1 % to 0.5 % of the aminosiloxane ester copolymer on the textile, based on dry weight of the textile.
  • step ii) After the emulsion is applied to the textile, it can be dried in step ii) by any convenient means. Drying may be performed at ambient or elevated temperature (with heating). Alternatively, drying in step ii) may comprise heating.
  • Suitable fibers may have the form of threads, strands, filaments, tows, or yams, and suitable fabrics include woven and nonwoven materials such as webs, mats, loop-formingly knitted or loop-drawingly knitted.
  • Suitable fibers may be of any natural or synthetic origin.
  • textiles which can be treated by the process of this invention, include those of natural origin such as cotton, hemp, linen, silk, and wool; synthetics such as polyester, polyamide, polyacrylonitrile, polyolefins such as polyethylene and polypropylene, polyvinyl alcohol; interpolymers of vinyl acetate, rayon, polyurethane; manmade and/or regenerated cellulosics; and combinations and blends of two or more thereof.
  • the textile fabrics can be present in the form of fabric webs or garments or parts of garments.
  • aqueous aminosiloxane ester copolymer emulsions with the starting materials (as described in Table 1) in amounts shown below in Table 3 were prepared as described in PCT Patent Application Publication WO2023/278918 according to the conditions in Table 2.
  • an aminosiloxane ester copolymer, a surfactant, and a first amount of water were mixed by a high shear mixer. Three aliquots of dilution water were added, with mixing after each addition. The acetic acid solution was added and mixed. SYNPERONICTM 13/12 was then added at the end of the process.
  • Emulsification Process conditions for each step are shown below in Table 2. Amounts of each starting material (in weight %) are shown below in Table 3.
  • each emulsion was applied on a substrate via an exhaust method and dried, as follows:
  • the exhaust method was a batch wise process wherein an aminosiloxane ester copolymer (active) was transferred to a fabric substrate by desorption and absorption of the active from the emulsion (described in Tables 3, 5, and 6) to the substrate (mainly due to the substantivity of the particular emulsion).
  • the exhaust method was done relatively from a diluted bath on a machine such as jet, overflow or winch.
  • the exhaustion rate was relevant to ecological considerations of wastewater loads.
  • the conditions for the Exhaust method are shown below in Table 7.
  • each emulsion was applied on a substrate via a padding method and dried, as follows:
  • the padding method was a continuous process for emulsion application.
  • the aminosiloxane ester copolymer (active) (or the comparative active from a Comparative Example) was applied by forced application (padding) from relatively concentrated emulsions, which transferred the active onto the fabric.
  • the amount of active transfer was controlled by concentration of active and expression on substrate. For example, 60% expression meant 60% active was transferred on to the substrate. Expression was adjusted by controlling the pressure between two rollers of the padding mangle through which the substrate was squeezed. Conditions for padding are shown below in Table 8.
  • Water Absorbency Testing was performed according to: AATCC 79 - 2000. A water penetration value of less than 10 seconds, alternatively 1 to 2 seconds, indicated good hydrophilicity/quick absorption.
  • Example 2 demonstrated surprisingly low contact angle and water penetration values, even though the aminosiloxane ester copolymer had a longer DP dimethylsiloxane segment (84) compared to the other aminosiloxane ester copolymers tested (with 44 DP dimethylsiloxane segments) even though lengthening dimethylsiloxane segments would typically be expected to decrease hydrophilicity.
  • Example 5 the inventors surprisingly found that combining emulsions of an aminosiloxane ester copolymer and 8041 as actives produced the lowest contact angle of all samples tested, demonstrating a synergistic effect when combining a hydrophobic amino-functional siloxane and the aminosiloxane ester copolymer described herein.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention concerne un procédé de traitement d'un textile destiné à conférer un caractère hydrophile qui comprend l'application d'une émulsion de copolymère d'ester d'aminosiloxane sur le textile et le séchage du textile. L'émulsion de copolymère d'ester d'aminosiloxane comprend un tensioactif et de l'eau en plus du copolymère d'ester d'aminosiloxane.
PCT/US2024/056571 2023-12-26 2024-11-20 Utilisation de copolymères d'ester d'aminosiloxane pour le traitement de textiles Pending WO2025144523A1 (fr)

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WO2023278918A1 (fr) 2021-06-28 2023-01-05 Dow Silicones Corporation Copolymère d'ester d'aminosiloxane et procédés de préparation et d'utilisation du copolymère

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US1075864A (en) 1913-10-14 Scott & Williams Inc Hosiery.
DE1273099B (de) * 1961-09-27 1968-07-18 Union Carbide Corp UEberzugs- und Impraegniermittel zum Hydrophobieren von Oberflaechen
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US5387417A (en) 1991-08-22 1995-02-07 Dow Corning Corporation Non-greasy petrolatum emulsion
US6180117B1 (en) 1994-05-27 2001-01-30 General Electric Company Method of preparing microemulsions of amino silicone fluids and MQ resin mixtures
US5811487A (en) 1996-12-16 1998-09-22 Dow Corning Corporation Thickening silicones with elastomeric silicone polyethers
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