WO2016042085A1 - Compositions d'aminosiloxanes et d'oxydes métalliques - Google Patents

Compositions d'aminosiloxanes et d'oxydes métalliques Download PDF

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Publication number
WO2016042085A1
WO2016042085A1 PCT/EP2015/071341 EP2015071341W WO2016042085A1 WO 2016042085 A1 WO2016042085 A1 WO 2016042085A1 EP 2015071341 W EP2015071341 W EP 2015071341W WO 2016042085 A1 WO2016042085 A1 WO 2016042085A1
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WIPO (PCT)
Prior art keywords
radicals
compositions
carbon atoms
weight
general formula
Prior art date
Application number
PCT/EP2015/071341
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German (de)
English (en)
Inventor
Richard Becker
Franz Wimmer
Original Assignee
Wacker Chemie Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Wacker Chemie Ag filed Critical Wacker Chemie Ag
Publication of WO2016042085A1 publication Critical patent/WO2016042085A1/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
    • D06M15/37—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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • 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
    • D06M13/144—Alcohols; Metal alcoholates
    • 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
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups

Definitions

  • the invention relates to compositions of aminoalkyl-containing polydimethylsiloxane and metal alkoxides and their use for the treatment of substrates.
  • Fluorocarbon resin-based products are currently widely used for the oil-repellent finishing of surfaces.
  • EP 651089 is a combination of
  • Silica forms a poorly adherent layer on the substrate surface.
  • compositions (Z) relates to compositions (Z), the
  • R is unsubstituted or substituted with chlorine alkyl radicals
  • R 3 bivalent hydrocarbon radicals with 1-40
  • R 4 monovalent hydrocarbon radicals with 1-40
  • R 5 is a radical of the general formula III
  • R 6 is a bivalent radical of the general formula IV
  • x is the value 0 or a value from 1 to 40
  • y 1 or 2
  • a 0, 1, 2 or 3
  • b is the value 0, 1, 2 or 3 and
  • a + b have an average value of 1.5 to 2.5, with at most 20 mol% of the radicals R 1 being OH or OR, (ii) 0.5 to 100 parts by weight of a metal alkoxide;
  • M is a metal selected from Ti, Zr, Ge, Mn and Al, n is the valency of M,
  • R 7 monovalent hydrocarbon radicals 1-40
  • c is an integer 0, 1, 2, 3 or 4, and
  • d is an integer 0, 1 or 2
  • (v) contain at most 0.5 part by weight of silica.
  • compositions (Z) show excellent oil repellency on many substrates, especially fibers and textiles.
  • the substrates treated with the compositions (Z) show improved water and soil repellency.
  • the alkyl radicals R 1 and R may be linear, cyclic, branched, saturated or unsaturated.
  • the alkyl radicals R 1 and R may be linear, cyclic, branched, saturated or unsaturated.
  • the alkyl radicals R 1 and R may be linear, cyclic, branched, saturated or unsaturated.
  • the alkyl radicals R 1 and R may be linear, cyclic, branched, saturated or unsaturated.
  • the alkyl radicals R 1 and R may be linear, cyclic, branched, saturated or unsaturated.
  • Methoxy residue, ethoxy residue or -OH Preferably, at most 10 mol% of the radicals R 1 are OH or OR.
  • the divalent hydrocarbon radicals can be
  • radicals have 1 to 6 carbon atoms, particularly preferred
  • Alkylene radicals in particular propylene.
  • the monovalent hydrocarbon radicals R 4 can be any organic radicals.
  • radicals chlorine-substituted, linear, cyclic, branched, aromatic, saturated or unsaturated.
  • radicals chlorine-substituted, linear, cyclic, branched, aromatic, saturated or unsaturated.
  • R 4 1 to 6 carbon atoms particularly preferred are alkyl radicals. Particularly preferred substituents R 4 are methyl, ethyl, cyclohexyl and H.
  • b is 0 or 1.
  • a + b has an average value of 1.9 to 2.2.
  • x has the value 0 or a value of 1 to 18, more preferably 1 to 6.
  • radicals R 2 are -CH 2 N (R 4) 2, - (CH 2) 3 N (R 4) 2, - (CH 2) 3 (R 4) (CH 2) 2 N (R 4) 2, in particular aminoethylaminopropyl radical and cyclohexylaminopropyl radical.
  • the polydimethylsiloxane (P) is composed of at least 3, in particular at least 10 units and
  • the ratio of a to b is chosen so that the
  • Polydimethylsiloxane (P) has at least one amine number of 0.1 mequiv / g polydimethylsiloxane (P), preferably at least 0.6 mequiv / g polydimethylsiloxane (P).
  • the amine number of the Polydimethylsiloxane (P) is preferably at most 7
  • the aminoalkyl groups of the polydimethylsiloxane (P) may have been reacted in whole or in part by known chemical reactions; e.g. For example, a portion of the amine residues may be neutralized with inorganic or organic acids, e.g. Formic acid, acetic acid, propionic acid, oleic acid, stearic acid, citric acid, sulfuric acid or hydrochloric acid.
  • inorganic or organic acids e.g. Formic acid, acetic acid, propionic acid, oleic acid, stearic acid, citric acid, sulfuric acid or hydrochloric acid.
  • acid it is preferred to add acid in an amount of 0.05 to 1 mole
  • the polydimethylsiloxanes (P) are prepared by known chemical methods, e.g. Hydrolysis or equilibration.
  • Metals M preferably of Ti, Zr, Al or mixtures thereof.
  • n is determined by the valency of the metals
  • the monovalent hydrocarbon radicals may be linear, cyclic, branched, aromatic, saturated or unsaturated.
  • the radicals R 1 preferably have from 1 to 6 carbon atoms, particularly preferably alkyl radicals.
  • Particularly preferred substituents R 4 are methyl, ethyl, propyl, butyl and
  • metal alkoxides are aluminum (2-propylate), aluminum (2-butoxide), zirconium propylate,
  • compositions (Z) contain preferably from 5 to 70 parts by weight, in particular from 10 to 50 parts by weight, of metal alkoxide.
  • compositions (Z) contain no fluorine-containing silicon compounds, which means preferably that all silicon compounds used contain at most 10 ppm by weight of fluorine.
  • compositions (Z) preferably contain at most 0.1 part by weight, in particular at most 0.01 part by weight, of silica.
  • compositions (Z) may be in the form of mixtures, solutions or emulsions.
  • the mixtures, solutions or emulsions can be readily prepared by combining and mixing the individual components in any order.
  • compositions (Z) preferably contain solvents or solvent mixtures having a boiling point or boiling range of up to 120 ° C at 0.1 MPa.
  • solvents are water; Alcohols, such as methanol,
  • Amyl alcohol such as dioxane, tetrahydrofuran, diethyl ether, diisopropyl ether, diethylene glycol dimethyl ether; chlorinated hydrocarbons, such as dichloromethane, trichloromethane,
  • Hydrocarbons in particular aliphatic and aromatic hydrocarbons, such as pentane, n-hexane, hexane isomer mixtures, heptane, octane, benzine, petroleum ether, benzene, toluene,
  • Ketones such as acetone, methyl ethyl ketone, di- isopropyl ketone, methyl isobutyl ketone (MIBK); Esters, like
  • Particularly preferred solvents are the hydrocarbons.
  • the compositions (Z) contain preferably 10 to 10,000 parts by weight, in particular 100 to 5,000 parts by weight of solvent.
  • the compositions (Z) preferably contain emulsifiers.
  • emulsifiers all hitherto known, ionic and nonionic emulsifiers can be used both individually and in mixtures of different emulsifiers with which hitherto stable aqueous emulsions of
  • Organopolysiloxanes could be produced. Particular preference is given to fatty alcohol polyglycol ethers, alkylpolyglucosides, nonylphenol polyglycol ethers and quaternary ammonium salts of saturated and unsaturated fatty acids for oil in water
  • Emulsions For water-in-oil emulsions, all previously known emulsifiers can be used both individually and in mixtures of different emulsifiers. Particular preference is given to sorbitan oleate or stearates, glycerol oleates or stearates, fatty acid glycerol esters or siloxane polyglucosides (as described in EP 0 612 759) in combination with co-emulsifiers, e.g. Fatty alcohol polyglycol ethers, alkyl polyglucosides and nonylphenol polyglycol ethers.
  • co-emulsifiers e.g. Fatty alcohol polyglycol ethers, alkyl polyglucosides and nonylphenol polyglycol ethers.
  • compositions (Z) contain preferably 0.1 to 50 parts by weight, in particular 1 to 20 parts by weight
  • Emulsifier Emulsifier.
  • the compositions (Z) contain preferably 100 to 20,000 parts by weight, in particular 300 to 2,000 parts by weight Water.
  • the water is demineralized or saline water, preferably demineralized water.
  • compositions (Z) may contain, in addition to polydimethylsiloxane (P), other silicones, e.g. liquid silicones, cyclic silicones and / or solid silicones, such as silicon-containing waxes.
  • P polydimethylsiloxane
  • the compositions (Z) contain preferably 0 to 90 parts by weight, more preferably 10.0 to 60.0 parts by weight, in particular 20 to 50 parts by weight, of other silicones.
  • compositions (Z) may contain non-silicon containing waxes, such as natural waxes of vegetable origin, such as carnauba wax and candellila wax, montanic acid and
  • Montan ester waxes paraffin waxes, in particular anoxidized synthetic paraffins, polyethylene waxes, polyvinyl ether waxes and metal soap-containing waxes, carnauba wax,
  • Paraffin waxes and polyethylene waxes are preferred and
  • compositions (Z) preferably contain 0 to 100 parts by weight, in particular 5 to 50 parts by weight not
  • compositions (Z) may contain thickening agents.
  • thickeners are homopolysaccharides,
  • Polysaccharides and polyacrylates are particularly preferred.
  • compositions (Z) preferably contain from 0 to 60 parts by weight, in particular from 5 to 20 parts by weight of thickener.
  • the compositions (Z) may contain other ingredients such as preservatives, fragrances, acids, alkalis,
  • preservatives examples include formaldehyde, parabens, benzyl alcohol, propionic acid and their salts, and
  • compositions (Z) for the treatment of porous or non-porous, absorbent or non-absorbent substrates, preferably of celluloses, paper, natural and / or
  • Formulas is the silicon atom tetravalent. The sum of all
  • compositions (Z) give 100 wt .-%.
  • the amine number in mequiv / g corresponds to the amount of nitrogen in mmol in lg of substance.
  • the amine number is determined to be the number of ml of IN HCl required to neutralize 1 g of the substance.
  • all amounts and percentages are by weight, all pressures are 0.10 MPa (abs.) And all temperatures are 20 ° C. Examples:
  • the metal alkoxide was titanium tetrabutoxide.
  • Test Example 1 Water Repellency Test (Water / Alcohol - Drop Test)
  • This test method is used to determine the hydrophobic finish of textiles.
  • the treated sample to be tested is placed over a Petri dish so that there is no contact with the soil in the test area of the test sample.
  • test liquid W distilled water
  • test sample may be apart from each other.
  • the test sample may be used when setting up
  • the test fluids should not be touched with the pipette.
  • the test sample is covered with a Petri dish. From a
  • This oil repellency test is used to check the presence or effectiveness of an oleophobic finish on textiles. In this test, the resistance to wetting is determined by a specific series of test liquids.
  • the sample to be tested is laid out flat.
  • test specimen must not be touched with the pipette when placing the test fluids. Observe from an angle of approximately 45 ° for 15 seconds. If after 15 seconds no wetting of the leather or no
  • polydimethylsiloxane and metal alkoxide also shows a good water repellency but no oil repellency.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Paints Or Removers (AREA)
  • Silicon Polymers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)

Abstract

La présente invention a pour objet des compositions (Z) comprenant (i) 100 parties en poids de polydiméthylsiloxane (P) présentant des groupes aminoalkyle ayant un nombre d'amines d'au moins 0,1 méquivalent/g de polydiméthylsiloxane (P), constitué de motifs de formule générale (I) R1 aR2 bSiO(4-a-b/2) (ii) 0,5 à 100 parties en poids d'un oxyde métallique choisi à partir d'oxydes métalliques monomères de formule générale (V) M[(OH2(CH2)c)d OR7]n et R1, R2, M, R7, a, c, d et n qui ont les significations données à la revendication 1, (iv) aucun composé de silicium fluoré et (v) au plus 0,5 partie en poids d'acide silicique. L'invention concerne également leur utilisation pour traiter des substrats poreux ou non poreux et absorbants ou non absorbants.
PCT/EP2015/071341 2014-09-19 2015-09-17 Compositions d'aminosiloxanes et d'oxydes métalliques WO2016042085A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102014218864.4A DE102014218864A1 (de) 2014-09-19 2014-09-19 Zusammensetzungen von Aminosiloxanen und Metallalkoxiden
DE102014218864.4 2014-09-19

Publications (1)

Publication Number Publication Date
WO2016042085A1 true WO2016042085A1 (fr) 2016-03-24

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WO (1) WO2016042085A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018091077A1 (fr) 2016-11-16 2018-05-24 Wacker Chemie Ag Composition contenant des composés organosiliciés à fonction bêta-cétocarbonyle

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0055606A1 (fr) * 1980-12-29 1982-07-07 Toray Silicone Company Limited Emulsions de silicone à fonction amino
EP0113992A1 (fr) * 1982-12-27 1984-07-25 Dow Corning Corporation Aminosiloxanes à une composante durcis par l'humidité pour fixer et conditionner les cheveux
US4846886A (en) 1988-05-05 1989-07-11 Dow Corning Corporation Water beading-water shedding repellent composition
EP0612759A1 (fr) 1993-02-26 1994-08-31 Wacker-Chemie GmbH Composés organosilicié comportant un reste glycosidique et procédé pour leur préparation
EP0651089A1 (fr) 1993-10-27 1995-05-03 Dow Corning Toray Silicone Company, Limited Méthode de traitement de fils par adsorption

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0055606A1 (fr) * 1980-12-29 1982-07-07 Toray Silicone Company Limited Emulsions de silicone à fonction amino
EP0113992A1 (fr) * 1982-12-27 1984-07-25 Dow Corning Corporation Aminosiloxanes à une composante durcis par l'humidité pour fixer et conditionner les cheveux
US4846886A (en) 1988-05-05 1989-07-11 Dow Corning Corporation Water beading-water shedding repellent composition
EP0612759A1 (fr) 1993-02-26 1994-08-31 Wacker-Chemie GmbH Composés organosilicié comportant un reste glycosidique et procédé pour leur préparation
EP0651089A1 (fr) 1993-10-27 1995-05-03 Dow Corning Toray Silicone Company, Limited Méthode de traitement de fils par adsorption

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018091077A1 (fr) 2016-11-16 2018-05-24 Wacker Chemie Ag Composition contenant des composés organosiliciés à fonction bêta-cétocarbonyle
US10954343B2 (en) 2016-11-16 2021-03-23 Wacker Chemie Ag Compositions comprising beta-ketocarbonyl-functional organosilicon compounds

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