US3567499A - Textile materials and the process for finishing the same - Google Patents

Textile materials and the process for finishing the same Download PDF

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US3567499A
US3567499A US672718A US3567499DA US3567499A US 3567499 A US3567499 A US 3567499A US 672718 A US672718 A US 672718A US 3567499D A US3567499D A US 3567499DA US 3567499 A US3567499 A US 3567499A
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parts
active hydrogen
groups
textile
aqueous
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Wolfgang Klebert
Karl Schafer
Heinz Griepentrog
Friedrich Reich
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Bayer AG
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Bayer AG
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/653Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain modified by isocyanate compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/61Polysiloxanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04Polysiloxanes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/12Polysiloxanes containing silicon bound to hydrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/14Polysiloxanes containing silicon bound to oxygen-containing groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/22Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/22Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/28Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/70Siloxanes defined by use of the MDTQ nomenclature
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2279Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2352Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric

Definitions

  • the organo polysiloxane is reactive with the isocyanato prepolymer on the textile substrate in order to give the textile material a full pleasantly soft, supple hand and reduce susceptibility to soiling.
  • a further object of his invention is to provide textiles having an improved finish, an improved hand, a more supple feel and which have reduced susceptibility to soiling.
  • Another object of this invention is to provide an improved method of treating textile materials.
  • Still another object of this invention is to provide a method of finishing textiles and the finished textiles which may be based on cotton, cellulose, wool, silk, polyamides, polyurethane, polyesters, polycarbonate, polyacrylonitrile, polypropylene and the like.
  • This aqueous bath is used to treat the textile material which may then be dried and subjected to an after treatment with water in order to accelerate the curing of the polyurethane material in conjunction with the organic polysiloxane on the textile substrate.
  • the crux of this invention is the use of and reaction of the hydroxy organo polysiloxane with the isocyanato prepolymer in the aqueous bath on the textile substrate since this gives the textile materials an improved hand, better resistance to soiling, and a softer more supple feel than was heretofore known with textiles treated with organo polysiloxane isocyanato prepolymers.
  • the invention therefore could be briefly summarized as follows: the process involves treating textile materials with aqueous baths which contain:
  • reaction products containing isocyanate groups which reaction products are prepared from organic compounds of molecular weight about 500 to 10,000 containing at least two active hydrogen atoms and organic polyisocyanates, and
  • Examples of organic compounds containing at least two active hydrogen containing groups and having a molecular weight of 500 to 10,000 and which are suitable for preparing the reaction products containing isocyanate groups which, to be used according to the invention, are as follows: Polyalkylene glycols such as polyethlene, polypropylene, polybutylene or polyhexylene glycols or copolymers or graft polymers of the alkylene oxides on which these polyglycols are based and polythioetherglycols which are obtainable by condensation of thiodiglycol with itself or with polyalcohols that are free from sulphur.
  • Polyalkylene glycols such as polyethlene, polypropylene, polybutylene or polyhexylene glycols or copolymers or graft polymers of the alkylene oxides on which these polyglycols are based and polythioetherglycols which are obtainable by condensation of thiodiglycol with itself or with polyalcohols that are
  • Polyesters which are obtained by the condensation of dicarboxylic acids with polyalcohols or by condensation of hydroxycarboxylic acids are also suitable as well as polyester amides such as are described, for example, in US. patent specification No. 2,424,883, and polyacetals such as are described, for example, in US. patent specification No. 3,021,289.
  • compounds containing at least two active hydrogen atoms those having two or more free hydroxyl groups are preferably used, but those having free carboxyl, mercapto or amino groups are also suitable.
  • the molecular weights of these compounds may be up to 10,000 although the preferred range lies between 750 and 5,000.
  • low molecular weight compounds such as diols, for example, 1,4-butanediol, ethylene glycol, diethylene glycol and the like which have a modifying effect on the properties of the end products may also be used.
  • Any suitable organic polyisocyanate may be used for the preparation of the reaction products and are preferably aliphatic or cycloaliphatic diisocyanates. Examples of these include tetramethylene diisocyanate, hexamethylene diisocyanate, 1,4-cyclohexane diisocyanate, 4,4-dicyclohexylmethane diisocyanate, 2,4- and 2,6-hexahydrotoluylene diisocyanate and the like.
  • Aromatic diisocyanates such as p-phenylene diisocyanate and 2,4- or 2,6- toluylene diisocyanate as well as triisocyanates, such as the reaction product of the formula obtainable by reaction of 3 mols of hexamethylene diisocyanate and 1 mol of water are also suitable.
  • the preparation of the reaction products containing isocyanate groups may be performed by reacting the compounds which carry at least two active hydrogen atoms with a stoichiometric excess of polyisocyanate at elevated temperatures.
  • the reaction products Which contain isocyanate groups can also be utilized in the form of the known bisulphite addition products.
  • the organopolysiloxanes having two active hydrogen atoms that are to be used according to the invention include in particular compounds of the general formula B11810 T in which n is greater than 1 and not more than 3 and in which each substituent R is one of the radicals R, X-Y or Y-XY, where R represents an aliphatic, cycloaliphatic or aromatic hydrocarbon radical which may, if desired, be substituted by an inert substituent, X represents an aliphatic or araliphatic bivalent or trivalent radical which may contain an ether, thioether, ester or amino group, and Y represents a hydroxyl, sulphydryl, carboxyl or carbonamide group or a secondary amino group, with the proviso that at least two siloxane units are of the formulae:
  • organopolysiloxanes described above can be used as starting materials for the reaction products containing isocyanate groups which are to be used according to the invention.
  • vinyl and divinyl monomers on which the polymers or copolymers to be used according to the invention may be based are as follows: ethylene, propylene, vinyl chloride, vinyl acetate, vinyl ethyl ether, styrene or divinylbenzene, butadiene, isoprene or chloroprene and a,,B-unsaturated carboxylic acids such as acrylic acid and methacrylic acid as well as their nitriles, esters and amides.
  • Polymers which contain groups capable of reacting with isocyanates are generally to be preferred; these include, for example, polymers or copolymers prepared from acrylic acid, methacrylic acid, their hydroxyalkyl esters or amides, as well as the copolymers which can be obtained when N-methylolacrylamide, N-methylolrnethacrylamide or their derivatives prepared by reacting them with alcohols containing at least one further functional group are copolymerized with other olefinically unsaturated compounds, e.g. by the process according to US. patent specification No. 3,243,399.
  • the proportion of organopolysiloxanes containing at least two active hydrogen atoms may be 1 to 20 equivalents percent, based on the reaction products containing isocyanate groups, provided that each isocyanate group is capable of reacting with one of the active hydrogen atoms of the organopolysiloxanes.
  • the ratio usually lies between 3 and 7 equivalents percent.
  • the ratio by weight between the reaction products which contain isocyanate groups and the polymers or cpolymers which may be used is preferably between 0.25 :1 and 4: 1.
  • the amount of reaction products containing isocyanate groups, organopolysiloxanes and, where present polymers or copolymers contained in the aqueous bath may also vary within wide limits, for example somewhere between 20 and 300 grams/liter. The most suitable concentration in the bath and the appropriate proportions of the individual components to each other can easily be determined from case to case by preliminary tests.
  • the impregnating baths can be prepared by emulsifying the reaction products which carry isocyanate groups and the organopolysiloxanes which have at least two active hydrogen atoms and which have been adjusted, if necessary, to a low viscosity by the addition of inert solvents that are immiscible with water, such as benzene, toluene, ethyl acetate, petrol or chlorinated hydrocarbons, by means of a high speed stirrer in water in which suitable emulsifiers such as alkylphenolpolyglycol ethers, commercial parafiin sulphonates, alkyl benzene sulphonates or the alkali salts of acid sulphur acid esters of higher aliphatic alcohols are dissolved in quantities of 0.5 to 10% by weight.
  • inert solvents such as benzene, toluene, ethyl acetate, petrol or chlorinated hydrocarbons
  • two emulsions each of which contains one of the components, may first be prepared separately and then combined, if desired with the addition of the polymers or copolymers in the form of their aqueous dispersions.
  • both components may be stirred successively into the same aqueous emulsifier solution by means of a high speed stirrer, and the polymer or copolymer emulsion may then be added to this emulsion.
  • a third method of preparation is possible with the use of polymers or copolymers.
  • a stable emulsion is first prepared from the organopolysiloxane and the polymer or copolymer emulsions, and this is then mixed with the emulsion of isocyanate groupcontaining reaction products, which last mentioned emulsion is prepared shortly before use. If desired the baths may then be diluted with water.
  • the treatment of the textile materials with the aqueous baths to be used according to the invention may be performed by steeping the textile materials in the baths and then squeezing them out or centrifuging them to reduce the weight increase to about 40 to 150%, preferably 70 to 100%, and then drying.
  • the aqueous bath may be sprayed on to the textile material which is then dried.
  • it is advisible to store the materials for a few days at room temperature after the treatment.
  • the process of storing the finished textile materials for several days, a process which is to be recommended especially in cases where less highly reactive, aliphatic isocyanates are used, can be shortened or even avoided by accelerating the reaction between the isocyanate groups and the compounds which contain active hydrogen atoms.
  • 0.1 to 10 grams/liter of water-soluble salts of metals of sub-Group I, II or VIII of the Periodic System of elements with lower aliphatic carboxylic acids are added to the aqueous bath.
  • the textile materials are impregnated and dried and this operation may be followed by a 3 to 30 minutes after-treatment in water at 10 to 100 C. which water may contain surface-active substances, 1 to 5 grams of hydrogen peroxide (30%) or 0.1 to 1 g. of catalysts which accelerate the isocyanate reaction with compounds containing active hydrogen atoms being added per liter of water at temperatures below 60 C.
  • the after-treatment may also be performed by treating the impregnated and dried textile materials with steam at to C. for /2 to 10 minutes.
  • Zinc salts of lower carboxylic acids are particularly suitable salts to add to the bath.
  • Suitable catalysts for the after treatment are, for example, tin compounds such as dibutyl tin dilaurate or dimaleate, aqueous solutions of stannous chloride stabilized with glycollic acid, tertiary amines such as triethylamine, dimethylcyclohexylamine, triethylenediamine and N-ethylmorpholine or the acetyl acetonates of nickel, cobalt or iron.
  • the process according to the invention makes it possible to obtain excellent finishes on textile materials of natural or synthetic origin, for example textile materials of cotton, regenerated cellulose, wool or silk as well as of polyamide, polyurethane, polyester, polycarbonate, polyacrylonitrile or polypropylene fibers, especially from the point of view of their crease resistance, abrasion resistance and dimensional stability.
  • the treated textile materials are distinguished by a full, pleasant, soft and supple handle and an increased dirt repellency.
  • the treated textiles are useful to make clothing such as trousers, coats and the like.
  • EXAMPLE 1 A blended fabric of about 55% polyacrylonitrile fibers and about 45% wool was treated with an aqueous bath which contained, per liter, about 20 parts of an emulsion of a reaction product containing isocyanate groups, about 15 parts of the mixture of an emulsion of an organopolysiloxane with the aqueous dispersion of a coploymer and about 0.3 part of zinc acetate.
  • the blended fabric of polyacrylonitrile fibers and wool was squeezed out to a bath uptake of about 90%, dried for about 10 minutes at 110 C. and then treated for up to about 1 minute with steam at 102 C.
  • the fabric, treated according to the invention has a soft, smooth handle and the following advantages compared to an untreated fabric:
  • the emulsion of the reaction product containing isocyanate groups was prepared as follows:
  • the mixture of the emulsion of an organopolysiloxane with the dispersion of a copolymer was prepared as follows:
  • Dry creasing angle Wet creasing angle formula 5 Warp Weft Warp HOCH Si(CH ⁇ O-Si(CH & I Untreated fabric 102 105 65 70 OeSHCHQFCHZOH aarzarrara was emulsified with about 596 parts or water which con- 0 0 0 tained about 4 parts of the sodium salt of an alkyl Fabric treated with 100 g.
  • the cotton 1 f T? f f 1 fabric treated according to the invention has a smooth, and i i part 0 Zmc acetate abnc 0 Po soft handle and a high wet creasing angle in addition to acrylommle fibers was Squeeze? out to a bath p? good abrasion resistance. The effects are largely resistant about dned t about 130 and then ticated wlth to Washing steam at about 102 C. for up to about 2 minutes.
  • the fabric treated according to the invention has a pleasant, smooth handle and improved response to creasing.
  • the fabric was Excess diisocyanate was then removed at about 160 squeezed out to a bath uptake of about 100%, dried at C. in a thin layer evaporator at about 0.1 mm. Hg: A 50% about 100 C. and then heated afterwards at C. for emulsion was then prepared from about 500 parts of the 5 minutes.
  • the rayon fabric treated according to the inresulting reaction product which contained about 5.7%
  • vention has a full, smooth Wool-like handle, good abrasion 75 by weight of free isocyanate groups, with the use of about 9 100 parts of ethyl acetate and about 400 parts of water with the addition of a commercial surface-active parafiin sulphonate.
  • the yarns were treated with the aqueous bath by immersion contrifuged to reduce the bath uptake to about 60% and dried at about 130 C.
  • the yarns treated according to the invention have a pleasant, soft handle and do not tend to felt or shrink when washed.
  • the process for finishing a textile material to impart an improved hand and a reduced susceptibility to soiling which comprises treating a textile material with an aqueous bath which consists of essentially of 1) an isocyanato prepolymer prepared by a process which comprises reacting an organic polyisocyanate with an organic compound having a molecular weight of about 500 to about 10,000 and containing at least two active hydrogen containing groups as determined by the Zerewitinoif method (2) and 1 to 20 equivalent percent, based on said prepolymer of an organopolysiloxane having a molecular weight of up to about 25,000 and containing at least two active hydrogen containing groups as determined by the Zerewitinoff method; and reacting said prepolymer (1) and said polysiloxane (2) in situ on said textile material.
  • said aqueous bath additionally contains 0.1 to g. per liter of water-soluble lower carboxylic acid salts of metals of Groups I, II or VIII, of the Periodic System of elements, and wherein after treating with said aqueous bath; said textile material is dried and then treated for 3 to 30 minutes in water at 10100 C. or for /2-10 minutes with steam at 100- 110 C., said water optionally including 1-5 g. of hydrogen peroxide or 0.1-l g. of catalysts which accelerate the reaction of isocyanate groups with compounds containing active hydrogen atoms.
  • a textile material treated according to the process of claim 1 wherein said aqueous composition also contains 0.1-10 g. per liter of a water-soluble lower carboxylic acid salt of a metal of Groups I, II, or VIII of the Periodic System of elements.
  • organopolysiloxane has the general formula RuSiO in which n is greater than 1 and not more than 3 and in which each substituent R is one of the radicals R, -XY, or
  • R, Y and X have the meaning indicated above and m is the integer 1 or 2, and the substituents R in the remaining siloxane units being exclusively the radicals R.

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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)
  • Polyurethanes Or Polyureas (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US672718A 1966-10-06 1967-10-04 Textile materials and the process for finishing the same Expired - Lifetime US3567499A (en)

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3668228A (en) * 1968-06-13 1972-06-06 Ciba Ltd Solutions of curing catalysts for polysiloxanes
US3852230A (en) * 1970-10-14 1974-12-03 Vyzk Ustav Kozedelny Impregnating compositions for fibrous sheet materials from polyurethane and olefin copolymer
US4052495A (en) * 1975-05-19 1977-10-04 Dow Corning Corporation Method of obtaining release of polyurethane polymers and compositions therefor
US4057595A (en) * 1975-05-19 1977-11-08 Dow Corning Corporation Method of modifying the physical properties of urethane elastomers
US4137360A (en) * 1973-09-07 1979-01-30 Bayer Aktiengesellschaft Microporous sheets and a process for making them
US4468492A (en) * 1983-07-15 1984-08-28 Ppg Industries, Inc. Polymeric organo functional silanes as reactive modifying materials
US4528343A (en) * 1981-06-22 1985-07-09 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Antithrombogenic elastomer, molded products of the same, and a process for manufacturing the same
WO1985005322A1 (en) * 1984-05-21 1985-12-05 Thoratec Laboratories Corporation Moisture vapor permeable materials
WO1985005373A1 (en) * 1984-05-21 1985-12-05 Thoratec Laboratories Corporation Moisture vapor permeable materials containing segmented block multipolymer
US4579964A (en) * 1983-03-31 1986-04-01 Union Carbide Corporation Alkoxysilyl functional silicones
US5120813A (en) * 1980-02-29 1992-06-09 Th. Goldschmidt Ag Moisture vapor permeable materials
US5258443A (en) * 1990-10-30 1993-11-02 Imperial Chemical Industries, Plc Curable aqueous composition comprising a high molecular weight silane functional polymer and a relatively low molecular weight silane functional polymer
US5886082A (en) * 1995-04-05 1999-03-23 Kansai Paint Co., Ltd. Aqueous coating composition
US5910535A (en) * 1996-05-03 1999-06-08 Decora, Incorporated Water based coating composition having sacrificial layer for stain removal
US6084020A (en) * 1994-08-16 2000-07-04 Decora, Incorporated Non-stick polymer-coated articles of manufacture, and process and coatings for the production thereof
US20100267861A1 (en) * 2007-12-07 2010-10-21 Benecke-Kaliko Ag. Polymer mixture
WO2013017033A1 (en) 2011-07-29 2013-02-07 Dow Corning (China) Holding Co., Ltd. Coating composition, method for coating surface of material using the same, and surface treated materials having the same

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3668228A (en) * 1968-06-13 1972-06-06 Ciba Ltd Solutions of curing catalysts for polysiloxanes
US3852230A (en) * 1970-10-14 1974-12-03 Vyzk Ustav Kozedelny Impregnating compositions for fibrous sheet materials from polyurethane and olefin copolymer
US3900621A (en) * 1970-10-14 1975-08-19 Vyzk Ustav Kozedelny Impregnating compositions for fibrous sheet materials
US4137360A (en) * 1973-09-07 1979-01-30 Bayer Aktiengesellschaft Microporous sheets and a process for making them
US4052495A (en) * 1975-05-19 1977-10-04 Dow Corning Corporation Method of obtaining release of polyurethane polymers and compositions therefor
US4057595A (en) * 1975-05-19 1977-11-08 Dow Corning Corporation Method of modifying the physical properties of urethane elastomers
US5120813A (en) * 1980-02-29 1992-06-09 Th. Goldschmidt Ag Moisture vapor permeable materials
US4686137A (en) * 1980-02-29 1987-08-11 Thoratec Laboratories Corp. Moisture vapor permeable materials
US4623347A (en) * 1981-06-22 1986-11-18 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Antithrombogenic elastomer products
US4528343A (en) * 1981-06-22 1985-07-09 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Antithrombogenic elastomer, molded products of the same, and a process for manufacturing the same
US4579964A (en) * 1983-03-31 1986-04-01 Union Carbide Corporation Alkoxysilyl functional silicones
US4468492A (en) * 1983-07-15 1984-08-28 Ppg Industries, Inc. Polymeric organo functional silanes as reactive modifying materials
WO1985005373A1 (en) * 1984-05-21 1985-12-05 Thoratec Laboratories Corporation Moisture vapor permeable materials containing segmented block multipolymer
WO1985005322A1 (en) * 1984-05-21 1985-12-05 Thoratec Laboratories Corporation Moisture vapor permeable materials
US5258443A (en) * 1990-10-30 1993-11-02 Imperial Chemical Industries, Plc Curable aqueous composition comprising a high molecular weight silane functional polymer and a relatively low molecular weight silane functional polymer
US6084020A (en) * 1994-08-16 2000-07-04 Decora, Incorporated Non-stick polymer-coated articles of manufacture, and process and coatings for the production thereof
US6120849A (en) * 1994-08-16 2000-09-19 Decora, Incorporated Process for producing coated articles of manufacture
US6153304A (en) * 1994-08-16 2000-11-28 Decora Incorporated Hydrophobic coating system for application to an inorganic, organic or metallic substrate
US5886082A (en) * 1995-04-05 1999-03-23 Kansai Paint Co., Ltd. Aqueous coating composition
US5910535A (en) * 1996-05-03 1999-06-08 Decora, Incorporated Water based coating composition having sacrificial layer for stain removal
US20100267861A1 (en) * 2007-12-07 2010-10-21 Benecke-Kaliko Ag. Polymer mixture
US8314179B2 (en) * 2007-12-07 2012-11-20 Benecke-Kaliko Ag Polymer mixture
WO2013017033A1 (en) 2011-07-29 2013-02-07 Dow Corning (China) Holding Co., Ltd. Coating composition, method for coating surface of material using the same, and surface treated materials having the same
EP2736961A4 (en) * 2011-07-29 2015-01-14 Dow Corning China Holding Co Ltd COATING COMPOSITION, METHOD FOR SURFACE COATING OF MATERIALS THEREFOR AND SURFACE-COATED MATERIALS THEREWITH

Also Published As

Publication number Publication date
CH476889A (de) 1969-09-30
FR1545897A (fr) 1968-11-15
NL6713562A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1968-04-08
DE1619032A1 (de) 1969-10-30
SE327387B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1970-08-24
BE704806A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1968-02-15
CH1398867A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1969-04-30
GB1179310A (en) 1970-01-28

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