US3420703A - Process for treating a textile material with an aqueous antistatic and handle-improving composition and the aqueous treating composition - Google Patents

Process for treating a textile material with an aqueous antistatic and handle-improving composition and the aqueous treating composition Download PDF

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US3420703A
US3420703A US455633A US45563365A US3420703A US 3420703 A US3420703 A US 3420703A US 455633 A US455633 A US 455633A US 45563365 A US45563365 A US 45563365A US 3420703 A US3420703 A US 3420703A
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liquor
aqueous
compounds
acid
treating
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Helmut Kirkschnek
Georg Von Finck
Mathieu Quaedvlieg
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • 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
    • D06M13/12—Aldehydes; Ketones
    • 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
    • D06M13/12—Aldehydes; Ketones
    • D06M13/123—Polyaldehydes; Polyketones
    • 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
    • D06M13/12—Aldehydes; Ketones
    • D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • D06M13/262—Sulfated compounds thiosulfates
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/372—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 nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • 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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • 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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • D06M15/427—Amino-aldehyde resins modified by alkoxylated compounds or alkylene oxides
    • 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
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • cationic interface-active compounds are compounds of the general formula in which R stands for a long-chain alkyl radical, such as CH (CH CH or for an alkyl-polyoxy, alkylene radical, such as (CH --CH O) CH -CH CH or their quaternisation products, and compounds of the general formula R-CONHCH CH NH-CH CH NHCONH in which R stands for a long chain alkyl radical, e.g. for the radical 15 CH2.
  • cationic polymeric compounds there may be used, for example, compounds of the formula of fibrous material such as wool, cotton, rayon, cellulose acetate, synthetic polyamides, polyesters, polyacrylonitrile and polypropylene by treating the fibrous material by exhaustion process with a heated aqueous liquor having an acid pH, the active ingredients of the liquor consisting essentially of (a) a cationic interface-active compound exemplified by R--N(CH -CH NHCO-NH or a cationic polymer thereof wherein R is a long chain alkyl radical, an alkyl-polyoxy-alkylene, or quaternization product thereof; I (b) a lower aliphatic aldehyde exemplified by formaldehyde and (c) an anionic interface-active or anionic polymeric compound exemplified by the ammonium salts of alkylaryl sulfonic acids.
  • fibrous material such as wool, cotton, rayon, cellulose acetate, synthetic polyamide
  • the present invention relates to a process for treating fibrous materials; more particularly it concerns a process wherein fibrous materials are treated by the exhaustion process, while heating, with an acidic aqueous liquor containing (a) cationic interface-active or cationic polymeric compounds which contain, in addition to a grouping at least one further grouping of this type or at least one amino group which possesses at least one hydrogen atom bound to the nitrogen atom;
  • wich x stands for a number of 3 to 100, preferably 5 to 15, or their quaternisation products, as well as compounds of the formula in which at stands for a number of 3 to 100, preferably a number of 5 to 15, or their quaternisation products which still contain at least one NH group.
  • X stands for the radical of a compound which contains at least two hydrogen atoms capable of reacting with alkylene oxides, for example, for radicals of polyhydroxy compounds, such as glycerol, trimethylol-propane, pentaerythritol and sorbitol
  • R denotes hydrogen or an alkyl radical
  • R means an aliphatic, cycloaliphatic or aromatic radical
  • R denotes hydrogen, an alkyl radical, an alkoxy radical, an alkoxyalkyl radical or an aryl radical
  • Z stands for an aliphatic, cycloaliphatic or aromatic radical containing at least 10 carbon atoms, preferably for the radical of stearyl alcohol, stearic acid, stearic acid amide, stearylamine, N-methyl-stearylamine or distearylamine, while m is a number of 2 to 6, n is a number of 1 to 4, p is
  • lower aliphatic aldehydes or of compounds capable of yielding lower aliphatic aldehydes there may be mentioned, for example, formaldehyde, polyoxymethylene dihydrate, acetaldehyde and glyoxal or hexamethylene-tetramine, dimethylol-urea, dimethylol-N,N-ethylene-urea, methylol compounds of melamine as well as the ethers of these methylol compounds with lower alcohols, especially with methyl alcohol, furthermore the methylol compounds of carboxylic acid amides, e.g. of formamide and acetamide.
  • carboxylic acid amides e.g. of formamide and acetamide.
  • the alkylol compounds formed from the compounds (a) and (b) include, for example, the reaction products of the cationic compounds mentioned above with formaldehyde, or the ethers obtained from these reaction 3 products with lower aliphatic alcohols, such as methanol or ethanol.
  • anionic interface-active compounds are the alkali metal or ammonium salts of alkylaryl-sulphonic acids, e.g. of dodecylbenzene-sulphonic acid, dibutylnaphthalene-sulphonic acid, and dinaphthyl-methane disulphonic acid, furthermore the alkali metal or ammonium salts of alkyl-sulphonic acids, eg, of hexadecyl-sulphonic acid, and also the alkali metal or ammonium salts of higher fatty acids, such as stearic acid or oleic acid, of dioctyl-sulphosuccinic acid ester, monofatty alcohol-sulphuric acid or -phosphoric acid esters fatty acid sarcosides or taurides, alkyl-polyoxyalkyleneor alkylaryl-polyoxyalkylene-carboxylic acids and -sulphonic acids.
  • alkylaryl-sulphonic acids
  • Suitable anionic polymeric compounds are, for example, the alkali metal or ammonium salts of glycollic acid etherified with cellulose, of polyvinyl-sulphonic acid and polyacrylic acid; the molecular weight of these polymeric compounds is advantageously about 1000 to 10,000.
  • the amounts or proportions of the components contained in the aqueous liquor may vary within wide limits; expedient amounts or proportions which ensure the optimum absorption can easily be determined by preliminary experiments.
  • the quantity of cationic compounds depends upon the desired amount to be applied; in general, it will amount to about 0.5-%, referred to be achieved by the exhaustion process and at comparatively low temperatures, depending upon the type of cationic compounds employed, on a great variety of fibrous materials, e.g. on fibres, threads, yarns, fabrics or knitted fabrics of natural and especially of synthetic origin, such as wool, cotton, rayon, cellulose acetate, synthetic polyamides, polyesters, polyacrylonitrile and polypropylene. It is noteworthy that the effects achieved are largely resistant to washing, and this already before the treated fibrous materials have been dried, so that the materials can be freed before the drying operation from any excess of liquor by rinsing.
  • agents suitable for the finish of fibrous materials for example, plasticisers, anti-slip agents and stiffening agents may also be used when carrying out the process according to the invention.
  • Example 1 Yarns of fibres of polyacrylonitrile, polyester, polyamide or cotton, or of rayon are treated in an open or closed apparatus which permits a mechanical circulation of the goods or the liquor, in a liquor-to-goods ratio of 40:1 with an aqueous liquor which contains, per litre, 0.5 g. of the cationic compound the weight of the fibrous material.
  • the quantity of lower aliphatic aldehydes or of aldehyde-yielding compounds is advantageously so chosen that more than 1 mol aldehyde, generally about 2-5 mol aldehyde, are present per one mol of cationic compound.
  • the anionic compounds are normally used in such a quantity that the equivalent ratio between the anionic and cationic compounds lies within the range of 0.5-3:1; it is expedient to choose the equivalent ratio at which a dilute aqueous acidic solution of the components, when heated to -55 C., shows the strongest cloudiness, since the power of the cationic compounds to draw on the fibrous materials, possibly together with anionic compounds, is then greatest.
  • Organic acids such as formic acid and oxalic acid, are advantageously used for acidifying the aqueous liquor.
  • the treatment of the fibrous materials according to the invention is expediently carried out by initially moving the fibres for 30 to minutes in an aqueous bath having a liquor-to-goods ratio of 20:1 to 50:1 containing the components concerned and having a pH value of, advantageously, 2 to 4, and raising the temperature during this period to about 60 C.; following the resulting ausorption of the cationic compounds, which can be recognised from the fact that the cloudy liquor has become clear, the temperature of the bath is raised to 65-70" C. and maintained at this level for about 15-30 minutes, While adjusting the pH value to a value below 3 in order to complete the reaction of the cationic compounds with the aldehydes on the fibrous materials.
  • the aldehydes instead of adding the aldehydes to the liquor from the start, it is also possible to add them to the liquor only during the treatment. If desired, the temperature of the liquor may also be raised above 70 C. to 90 to 100 C. and the duration of the treatment thus shortened, provided this is tolerated by the fibrous material.
  • the liquor also contains a defoaming agent based on silicone in a quantity of 0.025 g. per litre.
  • the liquor which is initially clear at room temperature, is heated to about 55 C. in the course of 15 minutes whereby a marked cloudiness appears. The temperature is then raised to C. within 15 to 20 minutes and the bath is kept at this temperature for a few minutes until the liquor has again become clear.
  • the temperature of the bath is then raised to -70 C., the pH value adjusted to 2.6 to 2.8 by the addition of oxalic acid, and the bath is kept at the same temperature for a further 30 minutes.
  • the liquor is then cooled to 30 C. by the addition of cold water, the yarns are rinsed with water at 30 C. for about 5 minutes, then centrifuged and dried in the usual manner in a drying cabinet at 50 to 60 C.
  • the yarns thus treated have a pleasant soft feel which is substantially resistant to washing.
  • Yarns of synthetic fibrous materials exhibit moreover an antistatic effect which is also substantially resistant to washing.
  • the ratio of cationic to anionic compound stated above, which is advantageous for achieving the optimum absorption, was established by a simple preliminary experiment in the following manner: six aqueous solutions each of which contained, per litre, 0.5 g. of the cationic compound and 1.25 g. of 40% formaldehyde and was adjusted with oxalic acid to a pH value of about 3, were mixed at 20 C. with different amounts of the anionic compound, viz. with 0.1 g., 0.2 g., 0.3 g., 0.4 g., 0.5 g. and 0.6 g., respectively, and the almost clear solutions thus prepared were then heated to 4555 C.; the solution containing 0.4 g.
  • Example2 The process described in Example 1 is modified in that the suitable amount of 40% formaldehyde is not added to the liquor from the start, but only in the course of the treatment at 50 to 65 C. The finishing effects thus achieved are the same as those obtained by the method according to Example 1.
  • Example 3 The process described in Example 1 is modified in that the liquor contains, instead of 0.4 g. of a 42% commercial sodium salt of monolauryl alcohol-sulphuric acid ester, per litre 0.4 g. of a 66% commercial sodium salt of oleic acid methyl tauride or 0.4 g. of a 70% commercial sodium salt of dibutyl-naphthalene-sulphonic acid.' The finishing effects thus achieved are the same as those obtained by the method according to Example 1.
  • Example 4 Yarns of fibres of polyacrylonitrile, polyester, polyamide or cotton, or of rayon are treated in a cheese dyeing apparatus, after a conventional dyeing and after careful rinsing, in a liquor-to-goods ratio of 20:1 with an aqueous liquor which contains, per liter, 1 g. of the cationic compound of Example 1, 2.5 g. of the 40% formaldehyde, .05 g. of the defoaming agent based on silicone, and corresponding to commercial sodium salt of monolauryl alcohol-sulfuric acid ester as generally described in Examples 1 and 5, the liquor having b en adjusted by means of oxalic acid to an initial pH value of 2.6.
  • the liquor which is almost clear at room temperature is then heated to about 55 C. within 15 minutes, while changing the direction of the circulating liquor as frequently as possible, whereby a marked cloudiness of the liquor becomes apparent.
  • the temperature of the liquor is then raised to 60 C. within 1520 minutes, while, starting after about minutes, the pH value is gradually adjusted to 2.2 by slowly adding a dilute aqueous oxalic acid solution in order to ensure a uniform and slow absorption.
  • the liquor is advantageously adjusted at the beginning to a pH value of 2.8-3, instead of to 2.6, and then gradually adjusted to a pH value of 2.2 in the course of the treatment.
  • the liquor which has become completely clear is maintained at pH 2.2 and at 65-70 C. for a further 30 minutes.
  • the liquor is then cooled to about 30 C. by the addition of cold water.
  • the yarns are then rinsed for 2-3 minutes and dried at 50-60 C. in the usual manner.
  • the fibrous material thus treated has a pleasant soft feel which is substantially resistant to washing; yarns of synthetic origin moreover exhibit an antistatic effect which is also substantially resistant to washing.
  • Example 5 Yarns of fibres of polyacrylonitrile, polyester, polyamide or cotton, or of rayon are treated in an open or closed apparatus which permits a mechanical circulation of the goods or the liquor, in a liquor-to-goods ratio of 40:1 with an aqueous liquor which contains at the start of the treatment, per litre, 0.5 g. of the cationic compound and 0.4 g. of a 42% commercial sodium salt of monolauryl alcohol-sulphuric acid ester, and has been adjusted with oxalic acid to a pH value of 4; the liquor also contains 0.2 g./litre of a defoaming agent based on silicone.
  • the slightly cloudy liquor is heated to about 55 C. in the course of 15 minutes, whereby the cloudiness increases.
  • a further 0.17 g. of a 42% commercial sodium salt of monolauryl alcohol-sulphuric acid ester are then added to the bath; the liquor is subsequently heated to 60 C. in the course of 15-20 minutes and kept at this temperature for a few minutes until it has become clear.
  • 1 gram of a 50% commercial dimethylol-N,N'-ethy eneurea is then added per litre of liquor, the pH value is adjusted to 2.6 by means of oxalic acid, and the liquor is kept at 65-70 C. for about 30 minutes.
  • the liquor is then cooled to 30 C. by the addition of cold water and the fibre material is rinsed for 2-5 minutes, then centrifuged and dried at 50-60 C. in a drying cabinet in the usual manner.
  • the yarns thus treated have a soft feel which is substantially resistant to washing, and exhibit to some extent also a hydrophobic effect.
  • Example 6 The process described in Example 1 is modified in that the liquor contains, per litre, 0.5 g. of pentamethylol-melamine or 1 g. of a 50% commercial dimethylol-N,N'-ethylene-urea, instead of 1.25 g. of 40% formaldehyde.
  • the finishing effects thus achieved are the same as those obtained by the method according to Example 1.
  • a method for improving the handle of and imparting antistatic properties to fibrous materials inclusive of one or more of wool, cotton, rayon, cellulose acetate, synthetic polyamides, polyesters, polyacrylonitrile and polypropylene comprising treating the fibrous material by exhaustion process with a heated aqueous liquor having an acid pH, the active ingredients of said liquor consisting essentially of (a) a cationic component comprising one of (1) the cationic interface-active compound selected from the group consisting of the corresponding quaternization product thereof wherein R is a long-chain alkyl or an alkylpolyoxy-alkylene radical; a compound of the formula wherein R is a long-chain alkyl radical; and a compound of the formula wherein X is an organic radical containing at least two hydrogen atoms reactive with alkylene oxides; m is 2-6; n is 1-4; p is ll00; q is 0-4; r is 1-100; R is a member selected from the group consisting of hydrogen and al
  • R is a Egg-Chain alkyl an y
  • a component selected from the group consisting of polyoxyalkylene radlcal a Compound of the (1) one of lower aliphatic aldehyde and a comformula ponent capable of yielding a lower aliphatic aldez z 2 z CO-NH hyde, and wherein R is a long-chain alkyl radical
  • an anionic component consisting of one of R (1) an anionic interface-active compound selected X 3 from the group consist
  • R is a member selected from the group con- (2) an anionic polymeric component inclusive of sisting of hydrogen, alkyl, alkoxy, alkoxyalkyl, one of an alkali metal and an ammonium salt and y and Z is a member Selected f m the of glyconic acid th -ifi d with cellulose, of group consisting of aliphatic and aromatic radicals containing at least 10 carbon atoms;
  • a cationic polymeric component selected from group consisting of polyvinyl sulphonic acid, and polyacrylic acid; the molecular weight of these polymeric compo- 40 nents being about WOO-10,000;
  • the method of claim 1 wherein the aqueous liquor 5.
  • a fabric-treating composition consisting of an aque- 117 133 8, 139,4, 141, 143, 26029.4, 29.6

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

United States Patent us. at 117-4395 Claims Int. Cl. C08g 41/00; C10m; D06m ABSTRACT OF THE DISCLOSURE A method of improving handle and antistatic properties 3,420,703 Patented Jan. 7, 1969 ICC Examples of cationic interface-active compounds are compounds of the general formula in which R stands for a long-chain alkyl radical, such as CH (CH CH or for an alkyl-polyoxy, alkylene radical, such as (CH --CH O) CH -CH CH or their quaternisation products, and compounds of the general formula R-CONHCH CH NH-CH CH NHCONH in which R stands for a long chain alkyl radical, e.g. for the radical 15 CH2.
As cationic polymeric compounds there may be used, for example, compounds of the formula of fibrous material such as wool, cotton, rayon, cellulose acetate, synthetic polyamides, polyesters, polyacrylonitrile and polypropylene by treating the fibrous material by exhaustion process with a heated aqueous liquor having an acid pH, the active ingredients of the liquor consisting essentially of (a) a cationic interface-active compound exemplified by R--N(CH -CH NHCO-NH or a cationic polymer thereof wherein R is a long chain alkyl radical, an alkyl-polyoxy-alkylene, or quaternization product thereof; I (b) a lower aliphatic aldehyde exemplified by formaldehyde and (c) an anionic interface-active or anionic polymeric compound exemplified by the ammonium salts of alkylaryl sulfonic acids.
The present invention relates to a process for treating fibrous materials; more particularly it concerns a process wherein fibrous materials are treated by the exhaustion process, while heating, with an acidic aqueous liquor containing (a) cationic interface-active or cationic polymeric compounds which contain, in addition to a grouping at least one further grouping of this type or at least one amino group which possesses at least one hydrogen atom bound to the nitrogen atom;
(b) lower aliphatic aldehydes or compounds yielding lower aliphatic aldehydes; and/or alkylol compounds formed from (a) and (b) or their ethers with lower alcohols; and
(c) anionic interface-active or anionic polymeric compounds;
whereupon the materials are squeezed or centrifuged and dried in the usual manner, a rinsing operation being inserted before drying, if desired.
in wich x stands for a number of 3 to 100, preferably 5 to 15, or their quaternisation products, as well as compounds of the formula in which at stands for a number of 3 to 100, preferably a number of 5 to 15, or their quaternisation products which still contain at least one NH group. Especially suitable are cationic interface-active compounds of the formula in which X stands for the radical of a compound which contains at least two hydrogen atoms capable of reacting with alkylene oxides, for example, for radicals of polyhydroxy compounds, such as glycerol, trimethylol-propane, pentaerythritol and sorbitol, R denotes hydrogen or an alkyl radical, R means an aliphatic, cycloaliphatic or aromatic radical, and R denotes hydrogen, an alkyl radical, an alkoxy radical, an alkoxyalkyl radical or an aryl radical, and Z stands for an aliphatic, cycloaliphatic or aromatic radical containing at least 10 carbon atoms, preferably for the radical of stearyl alcohol, stearic acid, stearic acid amide, stearylamine, N-methyl-stearylamine or distearylamine, while m is a number of 2 to 6, n is a number of 1 to 4, p is a number of l to 100, q is a number of 0 to 4, and r is a number of l to 100, or the quaternisation products thereof. Relevant compounds are described in Belgian patent specifications Nos. 639,105 and 638,860.
As lower aliphatic aldehydes or of compounds capable of yielding lower aliphatic aldehydes there may be mentioned, for example, formaldehyde, polyoxymethylene dihydrate, acetaldehyde and glyoxal or hexamethylene-tetramine, dimethylol-urea, dimethylol-N,N-ethylene-urea, methylol compounds of melamine as well as the ethers of these methylol compounds with lower alcohols, especially with methyl alcohol, furthermore the methylol compounds of carboxylic acid amides, e.g. of formamide and acetamide.
The alkylol compounds formed from the compounds (a) and (b) include, for example, the reaction products of the cationic compounds mentioned above with formaldehyde, or the ethers obtained from these reaction 3 products with lower aliphatic alcohols, such as methanol or ethanol.
Examples of anionic interface-active compounds are the alkali metal or ammonium salts of alkylaryl-sulphonic acids, e.g. of dodecylbenzene-sulphonic acid, dibutylnaphthalene-sulphonic acid, and dinaphthyl-methane disulphonic acid, furthermore the alkali metal or ammonium salts of alkyl-sulphonic acids, eg, of hexadecyl-sulphonic acid, and also the alkali metal or ammonium salts of higher fatty acids, such as stearic acid or oleic acid, of dioctyl-sulphosuccinic acid ester, monofatty alcohol-sulphuric acid or -phosphoric acid esters fatty acid sarcosides or taurides, alkyl-polyoxyalkyleneor alkylaryl-polyoxyalkylene-carboxylic acids and -sulphonic acids. Suitable anionic polymeric compounds are, for example, the alkali metal or ammonium salts of glycollic acid etherified with cellulose, of polyvinyl-sulphonic acid and polyacrylic acid; the molecular weight of these polymeric compounds is advantageously about 1000 to 10,000.
The amounts or proportions of the components contained in the aqueous liquor may vary within wide limits; expedient amounts or proportions which ensure the optimum absorption can easily be determined by preliminary experiments. For example, the quantity of cationic compounds depends upon the desired amount to be applied; in general, it will amount to about 0.5-%, referred to be achieved by the exhaustion process and at comparatively low temperatures, depending upon the type of cationic compounds employed, on a great variety of fibrous materials, e.g. on fibres, threads, yarns, fabrics or knitted fabrics of natural and especially of synthetic origin, such as wool, cotton, rayon, cellulose acetate, synthetic polyamides, polyesters, polyacrylonitrile and polypropylene. It is noteworthy that the effects achieved are largely resistant to washing, and this already before the treated fibrous materials have been dried, so that the materials can be freed before the drying operation from any excess of liquor by rinsing.
If desired, other agents suitable for the finish of fibrous materials, for example, plasticisers, anti-slip agents and stiffening agents may also be used when carrying out the process according to the invention.
The following examples serve to illustrate the invention without, however, limiting its scope.
Example 1 Yarns of fibres of polyacrylonitrile, polyester, polyamide or cotton, or of rayon are treated in an open or closed apparatus which permits a mechanical circulation of the goods or the liquor, in a liquor-to-goods ratio of 40:1 with an aqueous liquor which contains, per litre, 0.5 g. of the cationic compound the weight of the fibrous material. The quantity of lower aliphatic aldehydes or of aldehyde-yielding compounds is advantageously so chosen that more than 1 mol aldehyde, generally about 2-5 mol aldehyde, are present per one mol of cationic compound. The anionic compounds are normally used in such a quantity that the equivalent ratio between the anionic and cationic compounds lies within the range of 0.5-3:1; it is expedient to choose the equivalent ratio at which a dilute aqueous acidic solution of the components, when heated to -55 C., shows the strongest cloudiness, since the power of the cationic compounds to draw on the fibrous materials, possibly together with anionic compounds, is then greatest. Organic acids, such as formic acid and oxalic acid, are advantageously used for acidifying the aqueous liquor.
The treatment of the fibrous materials according to the invention is expediently carried out by initially moving the fibres for 30 to minutes in an aqueous bath having a liquor-to-goods ratio of 20:1 to 50:1 containing the components concerned and having a pH value of, advantageously, 2 to 4, and raising the temperature during this period to about 60 C.; following the resulting ausorption of the cationic compounds, which can be recognised from the fact that the cloudy liquor has become clear, the temperature of the bath is raised to 65-70" C. and maintained at this level for about 15-30 minutes, While adjusting the pH value to a value below 3 in order to complete the reaction of the cationic compounds with the aldehydes on the fibrous materials.
Instead of adding the aldehydes to the liquor from the start, it is also possible to add them to the liquor only during the treatment. If desired, the temperature of the liquor may also be raised above 70 C. to 90 to 100 C. and the duration of the treatment thus shortened, provided this is tolerated by the fibrous material.
By means of the process according to the invention valuable effects, for example, softening and hydrophobing efiects, crease-proof and anti-static effects can CHr-(CHz) tr-CH;
1.25 g. of 40% formaldehyde and 0.4 g. of a 42% commercial sodium salt of monolauryl alcohol-sulphuric acid ester, and which has been adjusted with oxalic acid to a pH value of 2.6; the liquor also contains a defoaming agent based on silicone in a quantity of 0.025 g. per litre. The liquor which is initially clear at room temperature, is heated to about 55 C. in the course of 15 minutes whereby a marked cloudiness appears. The temperature is then raised to C. within 15 to 20 minutes and the bath is kept at this temperature for a few minutes until the liquor has again become clear. The temperature of the bath is then raised to -70 C., the pH value adjusted to 2.6 to 2.8 by the addition of oxalic acid, and the bath is kept at the same temperature for a further 30 minutes. The liquor is then cooled to 30 C. by the addition of cold water, the yarns are rinsed with water at 30 C. for about 5 minutes, then centrifuged and dried in the usual manner in a drying cabinet at 50 to 60 C. The yarns thus treated have a pleasant soft feel which is substantially resistant to washing. Yarns of synthetic fibrous materials exhibit moreover an antistatic effect which is also substantially resistant to washing.
The ratio of cationic to anionic compound stated above, which is advantageous for achieving the optimum absorption, was established by a simple preliminary experiment in the following manner: six aqueous solutions each of which contained, per litre, 0.5 g. of the cationic compound and 1.25 g. of 40% formaldehyde and was adjusted with oxalic acid to a pH value of about 3, were mixed at 20 C. with different amounts of the anionic compound, viz. with 0.1 g., 0.2 g., 0.3 g., 0.4 g., 0.5 g. and 0.6 g., respectively, and the almost clear solutions thus prepared were then heated to 4555 C.; the solution containing 0.4 g. of the anionic compounds per litre thereby exhibited the strongest cloudiness, whereas the solutions which contained 0.3 g. and 0.5 g. of the anionic compound showed only a slight cloudiness, and the solutions containing 0.1 g., 0.2 g. and 0.6 g. of the anionic compound exhibited practically no cloudiness at all.
Example2 The process described in Example 1 is modified in that the suitable amount of 40% formaldehyde is not added to the liquor from the start, but only in the course of the treatment at 50 to 65 C. The finishing effects thus achieved are the same as those obtained by the method according to Example 1.
Example 3 The process described in Example 1 is modified in that the liquor contains, instead of 0.4 g. of a 42% commercial sodium salt of monolauryl alcohol-sulphuric acid ester, per litre 0.4 g. of a 66% commercial sodium salt of oleic acid methyl tauride or 0.4 g. of a 70% commercial sodium salt of dibutyl-naphthalene-sulphonic acid.' The finishing effects thus achieved are the same as those obtained by the method according to Example 1.
Example 4 Yarns of fibres of polyacrylonitrile, polyester, polyamide or cotton, or of rayon are treated in a cheese dyeing apparatus, after a conventional dyeing and after careful rinsing, in a liquor-to-goods ratio of 20:1 with an aqueous liquor which contains, per liter, 1 g. of the cationic compound of Example 1, 2.5 g. of the 40% formaldehyde, .05 g. of the defoaming agent based on silicone, and corresponding to commercial sodium salt of monolauryl alcohol-sulfuric acid ester as generally described in Examples 1 and 5, the liquor having b en adjusted by means of oxalic acid to an initial pH value of 2.6. The liquor which is almost clear at room temperature is then heated to about 55 C. within 15 minutes, while changing the direction of the circulating liquor as frequently as possible, whereby a marked cloudiness of the liquor becomes apparent. The temperature of the liquor is then raised to 60 C. within 1520 minutes, while, starting after about minutes, the pH value is gradually adjusted to 2.2 by slowly adding a dilute aqueous oxalic acid solution in order to ensure a uniform and slow absorption. When using cheese apparatus with a particularly vigorous liquor circulation, the liquor is advantageously adjusted at the beginning to a pH value of 2.8-3, instead of to 2.6, and then gradually adjusted to a pH value of 2.2 in the course of the treatment. After the stated time, the liquor which has become completely clear, is maintained at pH 2.2 and at 65-70 C. for a further 30 minutes. The liquor is then cooled to about 30 C. by the addition of cold water. The yarns are then rinsed for 2-3 minutes and dried at 50-60 C. in the usual manner. The fibrous material thus treated has a pleasant soft feel which is substantially resistant to washing; yarns of synthetic origin moreover exhibit an antistatic effect which is also substantially resistant to washing.
Example 5 Yarns of fibres of polyacrylonitrile, polyester, polyamide or cotton, or of rayon are treated in an open or closed apparatus which permits a mechanical circulation of the goods or the liquor, in a liquor-to-goods ratio of 40:1 with an aqueous liquor which contains at the start of the treatment, per litre, 0.5 g. of the cationic compound and 0.4 g. of a 42% commercial sodium salt of monolauryl alcohol-sulphuric acid ester, and has been adjusted with oxalic acid to a pH value of 4; the liquor also contains 0.2 g./litre of a defoaming agent based on silicone. The slightly cloudy liquor is heated to about 55 C. in the course of 15 minutes, whereby the cloudiness increases. A further 0.17 g. of a 42% commercial sodium salt of monolauryl alcohol-sulphuric acid ester are then added to the bath; the liquor is subsequently heated to 60 C. in the course of 15-20 minutes and kept at this temperature for a few minutes until it has become clear. 1 gram of a 50% commercial dimethylol-N,N'-ethy eneurea is then added per litre of liquor, the pH value is adjusted to 2.6 by means of oxalic acid, and the liquor is kept at 65-70 C. for about 30 minutes. The liquor is then cooled to 30 C. by the addition of cold water and the fibre material is rinsed for 2-5 minutes, then centrifuged and dried at 50-60 C. in a drying cabinet in the usual manner. The yarns thus treated have a soft feel which is substantially resistant to washing, and exhibit to some extent also a hydrophobic effect.
Example 6 The process described in Example 1 is modified in that the liquor contains, per litre, 0.5 g. of pentamethylol-melamine or 1 g. of a 50% commercial dimethylol-N,N'-ethylene-urea, instead of 1.25 g. of 40% formaldehyde. The finishing effects thus achieved are the same as those obtained by the method according to Example 1.
We claim:
1. A method for improving the handle of and imparting antistatic properties to fibrous materials inclusive of one or more of wool, cotton, rayon, cellulose acetate, synthetic polyamides, polyesters, polyacrylonitrile and polypropylene, comprising treating the fibrous material by exhaustion process with a heated aqueous liquor having an acid pH, the active ingredients of said liquor consisting essentially of (a) a cationic component comprising one of (1) the cationic interface-active compound selected from the group consisting of the corresponding quaternization product thereof wherein R is a long-chain alkyl or an alkylpolyoxy-alkylene radical; a compound of the formula wherein R is a long-chain alkyl radical; and a compound of the formula wherein X is an organic radical containing at least two hydrogen atoms reactive with alkylene oxides; m is 2-6; n is 1-4; p is ll00; q is 0-4; r is 1-100; R is a member selected from the group consisting of hydrogen and alkyl; R is a member selected from the group consisting of aliphatic, cycloaliphatic and aromatic radicals; R is a member selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxy- 7 8 alkyl, and aryl; and Z is a member selected from ous liquor having an acid pH, the active ingredients of the group consisting of aliphatic and aromatic said liquor consisting essentially of radicals containing at least 10 carbon atoms; (a) a cation component comprising one of (l) the cationic interface-active compound se- (2) a cationic polymeric component selected from 5 lasted from the group conslstmg of the group consisting of RN(CH CH NHCO-NH H2N-C ONH[CH2CH2?I-CH2CH2NH- OC-(CHz)5-CONH] xoHzoHn -CHiomNIt-o O-NH:
C2115 C2H5 and the corresponding quaternization product the corresponding quaternization product therethereof wherein x is an integer of 3-100. of, wherein R is a Egg-Chain alkyl an y (b) a component selected from the group consisting of polyoxyalkylene radlcal; a Compound of the (1) one of lower aliphatic aldehyde and a comformula ponent capable of yielding a lower aliphatic aldez z 2 z CO-NH hyde, and wherein R is a long-chain alkyl radical; and a (2) an alkylol formed from (a) and (b) (1); and compound of the formula (3) the corresponding ether of (2) with a lower OH 0 H alcohol; and (oHHbH-o),,on,- bH-orn-NH- R2-NH -b-N (c) an anionic component consisting of one of R (1) an anionic interface-active compound selected X 3 from the group consisting of dialkyl-sulphof R succinic acid ester, monofatty alcohol-sulphuric 2 O)tCHzGH-CH2Z]n acid ester, monofatty alcohol-phosphoric acid wherein X is an organic radical containing at ester, fatty acid sarcoside, fatty acid tauride, 164st two hydrogen atoms feafltive With ky alkyl-polyoxy alkylene-carboxylic acid, alkyl- Oxldes; m 1S 14; P 15 1-100; 4 1S r is 1-100; R is a member selected from the group consisting of hydrogen and alkyl; R is a member selected from the group consisting of aliphatic, cycloaliphatic-and aromatic radicals;
aryl-polyoxy alkylene-sulphonic acid, and the alkali metal or ammonium salts of alkylaryl sulphonic acids, of alkyl sulphonic acids, and of higher fatty acids; and R is a member selected from the group con- (2) an anionic polymeric component inclusive of sisting of hydrogen, alkyl, alkoxy, alkoxyalkyl, one of an alkali metal and an ammonium salt and y and Z is a member Selected f m the of glyconic acid th -ifi d with cellulose, of group consisting of aliphatic and aromatic radicals containing at least 10 carbon atoms;
(2) a cationic polymeric component selected from group consisting of polyvinyl sulphonic acid, and polyacrylic acid; the molecular weight of these polymeric compo- 40 nents being about WOO-10,000;
Hits-o ONH[CH;CH;NH.CH;CHNH. o G(CHi) -C ONH];CH2(CH2)16CH2 the ratio in molar equivalents of (a), (b) and (c) being i and the corresponding quaternization product about 1:2-5:3. thereof wherein x is an integer of 3-100.
2. The method of claim 1 wherein the aqueous liquor 5. The composition of claim 4 wherein the aqueous contains about .5-10% by Weight of fib t i l f liquor contains a ratio of anionic to cationic components the (a) cationic component and about 2 5 mol of the of about .5-3:1 and is maintained at a of about 2-4. (b) alhehyde component per mol of cationic component; the equivalent ratio of anionic to cationic components References C'ted being about .5-3:1, and the pH of the aqueous liquor is UNITED STATES PATENTS about 2,694,688 11/1954 Hughes.
3. The method of claim 1 wherein the fibrous material 2,715,078 8 195 5 C h is treated for about 30-40 minutes in the aqueous bath 3,044,962 7/1962 Brunt et al. 252110 having a liquor-to-goods ratio of about 2050:1 and a pH of 2-4, maintaining a temperature of liquor and ma- WILLIAM MARTIN, Primary Examinerterial at about 60 C. to effect absorption of the cationic T, G DAVIS, Assistant Examiner. compounds, and thereafter raising the temperature to about 70 c. at a pH below 3. Cl
4. A fabric-treating composition consisting of an aque- 117 133 8, 139,4, 141, 143, 26029.4, 29.6
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,420,703 January 7, 1969 Helmut Kirschnek et a1.
It is certified that error appears in the above identified patent and that said Letters Patent are hereby corrected as shown below:
Columns 1 and 2, lines 18 to 23, the righthand portion of the formula reading "NHCONH" should read NH-CO-NH Column 5, lines 64 to 75, that portion of the formula reading (1H CH CH -O-CH -CH-O- should read CH -O-CH -CH-O Column 7, line 52, "alhehyde" should read aldehyde Column 8, lines 21 to 27, that portion of the formula reading R 1 [(CO -CH-O) should read [(CH -CH-0) Column 8, line 46, that portion of the formula reading Signed and sealed this 24th day of March 1970.
(SEAL) Attest:
EDWARD M.FLETCHER,JR. WILLIAM E SCHUYLER, JR. Attesting Officer Commissioner of Patents
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US3563375A (en) * 1967-08-08 1971-02-16 Auby Prod Chim Method of selectively separating solid particles by electrostatic sorting in fluidized bed
US4002785A (en) * 1973-02-27 1977-01-11 Sandoz Ltd. Organic compound
US4170682A (en) * 1977-05-18 1979-10-09 Kellwood Company Treatment of nylon fabric for wettability and product thereof
US4719099A (en) * 1977-03-15 1988-01-12 L'oreal Composition and process for the treatment of keratin materials with polymers
US4761273A (en) * 1981-05-08 1988-08-02 L'oreal Composition in the form of an aerosol foam, based on a cationic polymer and an anionic polymer
EP0587988A2 (en) * 1992-08-31 1994-03-23 W.L. Gore & Associates GmbH Oleophobic and/or permanent hydrophobic modification at polymeric surfaces, process for their preparation and application
US5775303A (en) * 1995-06-30 1998-07-07 Cummins Engine Company, Inc. High Pressure Fuel Line Connection
CN106381699A (en) * 2016-10-13 2017-02-08 无锡市华诚印染剂厂 Anti-wrinkling antistatic fabric softener

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* Cited by examiner, † Cited by third party
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FR2434888A1 (en) * 1978-08-29 1980-03-28 Iws Nominee Co Ltd Shrink-proofing wool etc. - by treating fabric with water soluble hardenable polymer in aq. medium, then adding deposition agent

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US2694688A (en) * 1953-02-27 1954-11-16 Du Pont Antistatic compositions for textiles
US2715078A (en) * 1948-10-27 1955-08-09 Monsanto Chemicals Process of impregnating cellulosic material with thermosetting resin
US3044962A (en) * 1957-10-31 1962-07-17 British Nylon Spinners Ltd Preparation of detergent compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2715078A (en) * 1948-10-27 1955-08-09 Monsanto Chemicals Process of impregnating cellulosic material with thermosetting resin
US2694688A (en) * 1953-02-27 1954-11-16 Du Pont Antistatic compositions for textiles
US3044962A (en) * 1957-10-31 1962-07-17 British Nylon Spinners Ltd Preparation of detergent compositions

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3563375A (en) * 1967-08-08 1971-02-16 Auby Prod Chim Method of selectively separating solid particles by electrostatic sorting in fluidized bed
US4002785A (en) * 1973-02-27 1977-01-11 Sandoz Ltd. Organic compound
US4719099A (en) * 1977-03-15 1988-01-12 L'oreal Composition and process for the treatment of keratin materials with polymers
US4170682A (en) * 1977-05-18 1979-10-09 Kellwood Company Treatment of nylon fabric for wettability and product thereof
US4761273A (en) * 1981-05-08 1988-08-02 L'oreal Composition in the form of an aerosol foam, based on a cationic polymer and an anionic polymer
EP0587988A2 (en) * 1992-08-31 1994-03-23 W.L. Gore & Associates GmbH Oleophobic and/or permanent hydrophobic modification at polymeric surfaces, process for their preparation and application
EP0587988A3 (en) * 1992-08-31 1994-04-06 W.L. Gore & Associates GmbH Oleophobic and/or permanent hydrophobic modification at polymeric surfaces, process for their preparation and application
US5856246A (en) * 1992-08-31 1999-01-05 Witzko; Richard Permanent hydrophobic and oleophotic modification for polymer surfaces and process of making same
US5775303A (en) * 1995-06-30 1998-07-07 Cummins Engine Company, Inc. High Pressure Fuel Line Connection
CN106381699A (en) * 2016-10-13 2017-02-08 无锡市华诚印染剂厂 Anti-wrinkling antistatic fabric softener

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