US2926064A - Process for making wool resistant to felting and shrinking - Google Patents

Process for making wool resistant to felting and shrinking Download PDF

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Publication number
US2926064A
US2926064A US593312A US59331256A US2926064A US 2926064 A US2926064 A US 2926064A US 593312 A US593312 A US 593312A US 59331256 A US59331256 A US 59331256A US 2926064 A US2926064 A US 2926064A
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United States
Prior art keywords
wool
epoxide
solution
group
aqueous bath
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US593312A
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English (en)
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Rapp Alfred
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Boehme Fettchemie GmbH
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Boehme Fettchemie GmbH
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    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
    • D06M11/54—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur dioxide; with sulfurous acid or its salts
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/08—Oxirane

Definitions

  • This invention relates to a process for making wool and wool-containing textile fabrics resistant to felting and shrinking, which comprises treating the wool or fabric with fat-like or resin-like compounds containing epoxide groups and with compounds having a halogenating and/or oxidizing eifect.
  • wool and wool-containing textile materials can be made resistant against felting and shrinking by a treatment with fat-like or resin-like compounds containing epoxide groups and with compounds having a halogenating and/or oxiding effect.
  • the process in accordance with the present invention which can be carried out in a single bath, is characterized over the known processes by a substantial improvement in the resistance against felting and shrinking produced the-reby in the wool fiber.
  • the treatment period is substantially reduced and a considerable saving in chlorine is achieved, so that the wool is treated under mild conditions.
  • the treated wool does not turn yellow and has a very pleasant and soft feel. Fin-ally, the effects achieved thereby are maintained 'even after repeated launderings of the treated wool and wool-containing fabric;
  • the epoxide compounds used for the treatment of wool in accordance with the present invention are known compounds and can be produced according to well known methods.
  • Compounds of this type are, for example, the reaction products of epihalogenhydrins with compounds which contain one or more exchangeable hydrogen atoms linked tothe molecule through oxygen, sulfur or nitrogen atoms; for example in the form of hydroxyl, sulfhydryl, carboxyl, amino, carbonamide, carbohydrazide or sulfonamide groups.
  • Other epoxide compounds suitable for the present process are those which are formed by a reaction between glycide or its derivatives with the chlorides of monobasic or polybasic organic acids.
  • epoxide compounds are suitable for the present process which are produced by splitting off hydrogen halides from halogenhydiins, or also by a reaction of 2,926,064 Patented Feb. 23, 1960 peracids. with compounds which contain one or more double bonds in the molecule.
  • those compounds may be used which are produced by polymerization of unsaturated compounds containing epoxide groups.
  • Some of the above mentioned compounds have a fat-like and some a resin-like character, depending upon the type of starting material used.
  • low molecular epoxides such as butadienedioxide, are suitable for use in conjunction with the present process, but better effects are produced, as a rule, with the aid of fat-like or resinlike products.
  • -Fat-like epoxides which may be used for the process in accordance with this invention are, for example, the epoxidation products of unsaturated fats, such as soy bean oil, fish train oil or the fatty acids contained in these fats; also the glyceride esters of fatty acids and the like.
  • Suitable resin-like epoxides for the present process are, for example, resin-like glycide esters of succinic acid, adipic acid, sebacic acid, phthalic acid, terephthalic acid or benzenedisulfonic acid, as well as resin-like glycide esters of 'glycerine, resorcinol, hydroquinone, p,p'- diphenol, dioxydiphenylinethane, diphenylolpropane and the like, and also resin-like polymerization products of methacrylic acid glycide esters, .allyl glycide ethers, phthalic acidaallyl-glycide esters and the like.
  • the soft feel of the wool obtained by the process according to the present invention may be further improved by treating the wool with a combination of the resin-like and fat-like epoxide compounds of the type described above.
  • Suitable compounds having av hal ogenating and/or oxidizing effect useful for the present process include primarily hypochlorous acid or its salts, which are known to be useful in rendering wool resistant to felting, as well as hypobromites or persulfuric acid.
  • the epoxide compounds used in accordance with the present invention are preferably applied in combination with the halogenating and/or oxidizing agents in aqueous solution. Since the epoxide compounds are, in most cases, not water-soluble, they are advantageously dispersedin the solution with the aid of suitable emulsifiers. llnder some circumstances it is advantageous to firstdis'solve the epox-ide compounds in a suitable organic solvent and thereafter emulsify this solution in the aqueous treatment solution. For this purpose customary solvents maybe used, such as acetone, dioxane, .tetrahydrofurfuryl alcohol and diacetone alcohol.
  • the emulsifiers should be resistant against the halogenating or oxidizing agent present in the treatment solution. They may act simultaneously as wetting agents, and in' that capacity should be able to produce a wetting effect similar addition products which are derived from high molecular amines, canboxylic acids, acid amides and the like, are suitable.
  • the treatment solutions should advantageously contain 0.1 to 1 gram per liter, preferably 0.3 to 0L6 gra n per liter of the epoxide compound and about 0.1 to "0.5 gram per liter, preferably 0.3 gram per liter of active chlorine.
  • the impregnation of the wool with this solution is carried out in the usual fashion, for example, in a winch vat or in a yarn-dyeing machine. A treatment period of 5 to 10 minutes is sufficient.
  • the wool is rinsed in the usual manner, dechlorinated, if necessary, with such conventional agents as sodium thi'o-' sulfate or sodium bisulfite, and finally dried. It is not necessary to heat the treated wool to higher temperatures.
  • the process in accordance with the present invention can be carried out with pure wool as well as with fabrics containing 50% wool (wool-cotton, wool-regenerated l, wool-rayon, wool-perlon and he l ke-Yin;
  • the present invention can be distinguished over the first of the known processes by the active treatment compound used and over the latter of the known processes by the treatment conditions. Consequently the effects produced by the present process are entirely different.
  • Example I 50 grams of an epoxide compound (about 5 to 6% epoxide oxygen) produced by a reaction of 1 mol disodiumphthalate and 2 mols epichlorohydrin were dissolved in 200 cc. tetrahydrofurfuryl alcohol, and then 25 grams of the addition product of 5 mols ethyleneoxide to a fatty alcohol mixture wherein the fatty alcohols contained from 12 to 14 carbon atoms were added to this solution as an emulsifier.
  • the epoxide resin solution thus obtained was a clear yellow liquid which was stable over long periods of time.
  • Example II 45 grams of the epoxide resin used in Example I and 5 grams lauric acid glycide ester were dissolved in 200 cc. dioxane and 25 grams of the emulsifier described in Example I were added to this solution. 700 cc. of glacial acetic acid were then added to the emulsion.
  • Example III grams of the epoxide compound (about 5% epoxide oxygen) produced from 1 mol 2,2-diphenylolpropane and 2 mols epichlorohydrin and 5 grams coconut fatty acid glycide ester were dissolved in 200 cc. acetone and 25 grams of the emulsifier described in Example I were added thereto. Before using this solution for the treatment of wool, 700 cc. of glacial acetic acid were added.
  • Example IV 60 grams of an epoxide resin (about 5 to 6% epoxide oxygen) produced from 1 mol resorcinol and 2 mols epichlorohydrin were dissolved in 200 cc. diacetone alcohol and 25 grams of the emulsifier described in Example I were added to the solution. Before using the solution for treating wool, it was admixed with 700 cc. of glacial acetic acid. To produce the wool treatment solution, 3 grams per liter of persulfuric acid and 6 cc. per liter of the epoxide resin solution were stirred into cold water. A wool fabric was treated with this solution for 10 minutes in a winch vat using a solution ratio of 1:40. Subsequently, the treated wool was thoroughly rinsed and dried at 70 C. The wool fabric was fully resistant against felting and shrinking.
  • an epoxide resin about 5 to 6% epoxide oxygen
  • Example V 50 grams of the technical mixture of glycerine mono-, diand triglycide ether (about 9.5% epoxide oxygen) produced by reacting 3 mols epichlorohydrin with 1 mol glycerine and subsequent release of hydrochloric acid, were dissolved in 200 cc. acetone and 25 grams of the addition product of 6 mols ethyleneoxide to a fatty acid mixture containing carbon chains of 12 to 18 carbon atoms were addedd to the solution.
  • glycerine mono-, diand triglycide ether about 9.5% epoxide oxygen
  • Example VI 40 grams of the reaction product of adipic acid and epichlorohydrin (about 2 to 3% epoxide oxygen) were dissolved in 200 cc. diacetone alcohol, and 25 grams of the emulsifier described in Example I were added thereto. Before use, this solution was admixed with 700 cc. glacial acetic acid.
  • Example VII A polyester was produced from 3 mols adipic acid and 2 mols butanediol. The potassium salt of this polyester was then reacted with epichlorohydrin. 50 grams of this epoxide compound (about 2.7% epoxide oxygen) were dissolved in 200 cc. tetrahydrofurfuryl alcohol. Before use this solution was admixed with 700 cc. glacial acetic acid. For the production of the wool treatment solution 10 cc. per liter of the epoxide resin solution and 0.3 gram per liter active chlorine in the form of a technical chlorine solution were stirred into cold water. Wool in rope form was treated with this solution in an open dye vat for 10 minutes using a solution ratio of about 1:30. Thereafter the treated wool was dechlorinated, rinsed and dried at 70 C. The finished wool fabric was fully resistant against felting and shrinking.
  • Example VIII 50 grams of a polymethacrylic acid glycide ester (about 9 to 10% epoxide oxygen) were dissolved in 200 cc. acetone and 25 grams of the emulsifier described in Example I were added thereto.
  • a polymethacrylic acid glycide ester about 9 to 10% epoxide oxygen
  • acetone 25 grams of the emulsifier described in Example I were added thereto.
  • To produce the wool treatment solution cc. per liter of the epoxide resin solution, 12 cc. per liter glacial acetic acid and 0.3 gram per liter of active chlorine in the form of sodium hypochlorite were stirred into cold water. Wool fabric in rope form was treated with this solution in an open dye vat for 5 minutes using a solution ratio of 1:30. Thereafter the treated fabric 'was dechlorinated, rinsed and dried at 70 C. The finished wool fabric was fully resistant against felting and shrinking.
  • Example X A solution was produced from 50 grams of an epoxide soy bean oil (about 3.5% epoxide oxygen), 25 grams of the epoxide resin used in Example I, 75 cc. diacetone alcohol, 360 cc. glacial acetic acid and 25 grams of the emulsifier described in Example I.
  • To produce the wool treatment solution 5 cc. per liter of this solution and 0.3 gram per liter active chlorine in the form of a technical chlorine solution were stirred into cold water. Wool fabrics and wool-containing fabrics were treated in this solution for 5 to 10 minutes and were subsequently rinsed, dechlorinated and dried. The wool and wool-containing fabrics were fully resistant against felting and shrinking.
  • the method of simultaneously feltand shrinkproofing wool which comprises immersing said wool in a single aqueous bath containing essentially between 0.1 and 1.0 gm./liter of a polymerized epoxide compound having an epoxide oxygen content from 2 to 10%, said epoxide compound selected from the group consisting of carboxylic acid epoxy-alkyl esters, epoxy-alkyl ethers and epoxidized unsaturated fatty oils, an inert solvent selected from the group consisting of tetrahydrofurfuryl alcohol, dioxane, acetone and diacetone alcohol, an emulsifier selected from the group consisting of ethylene oxide addition products of fatty alcohols with 12 to 14 carbon atoms and ethylene oxide addition products of fatty acids with 12 to 18 carbon atoms, and a compound capable of releasing from 0.1 to 0.5 gm./liter of an element selected from the group consisting of chlorine and oxygen in aqueous solution, said compound selected from the group consisting of
  • the method of simultaneously feltand shrinkproofing Wool which comprises immersing said wool in a single aqueous bath containing essentially 0.1 to- 1.0 gm./liter of a polymerized dicarboxylic acid epoxy-alkyl ester having an epoxide oxygen content of 2 to 10%, an inert solvent'selected from the group consisting of tetrahydrofurfuryl alcohol, dioxane, acetone and diacetone alcohol, an emulsifier selected from the group consisting of ethylene oxide addition products of fatty alcohols with 12 to 14 carbon atoms and ethylene oxide addition products of fatty acids with 12 to 18 carbon atoms, andfrom 0.1 to 0.5, gm./liter active chlorine, allowing said wool to remain in said aqueous'bath at substantially room temperature for a suflicient amount of time ranging from about 5 to about 10 minutes to become thoroughly impregnated with said aqueous bath, removing the impregnated wool from the aqueous bath,
  • the method of simultaneously feltand shrinkproofing wool which comprises immersing said wool in a single aqueous bath containing essentially 0.1 to 1.0 gm./liter of a polymerized epoxy-alkyl ether having an epoxide oxygen content of 2 to 10%, an inert solvent selected from the group consisting of tetrahydrofurfuryl alcohol, dioxane, acetone and diacetone alcohol, an emulsifier selected from the group consisting of ethylene oxide addition products of fatty alcohols with 12 to 14 carbon atoms and ethylene oxide addition products of fatty acids with 12 to 18 carbon atoms, and from 0.1 to 0.5 gm./liter active chlorine, allowing said wool to remain in said aqueous bath at substantially room temperature for a suflicient amount of time ranging from about 5 to about 10 minutes to become thoroughly impregnated with said aqueous bath, removing the impregnated wool from the aqueous bath, dechlorinating the impregnated wool with
  • the method of simultaneously feltand shrinkproofing wool which comprises immersing said wool in a single aqueous bath containing essentially 0.1 to 1.0 gm./liter of a polymerized epoxidized unsaturated fatty oil having an cpoxide oxygen content of 2 to 10%, an
  • inert solvent selected from the group consisting of tetrahydrofurfuryl alcohol, dioxane, acetone and diacetone alcohol, an emulsifier selected from the group consisting of ethylene oxide addition products of fatty alcohols with 12 to 14 carbon atoms and ethylene oxide addition products of fatty acids with 12 to 18 carbon atoms, and from 0.1 to 0.5 gm./liter active chlorine, allowing said wool to remain in said aqueous bath at substantially room temperature for a suflicient amount of time ranging from about 5 to about 10 minutes to become thoroughly impregnated with said aqueous bath, removing the impregnated wool from the aqueous bath, dechlorinating the impregnated wool with a compound selected from the group consisting of sodium bisulfite and sodium thiosulfate, and drying the wool at a temperature of about70 C.
  • the method of simultaneously feltand shrinkproofing wool which comprises treating said wool in a and oxygen in aqueous solution, Said compound being present in suflicient amount to release from 0.1 to 0.5 gm./liter of said element, allowing said wool to remain in said aqueous bath at a substantially constant room temperature for a period of time ranging from about 5 to about 10 minutes, to cause impregnation of said wool with said solution.
  • the method of simultaneously feltand shrinkproofing wool which comprises immersing said wool in a single aqueous bath comprising between 0.1 and 1.0 gm./liter of a polymerized epoxide compound selected from the group consisting of carboxylic acid epoxyalkyl esters, epoxy-alkyl ethers and epoxidized unsaturated fatty oils and a compound capable of releasing an element selected from the group consisting of chlorine and oxygen in aqueous solution, said compound being present in sufficient amount to release from 0.1 to 0.5 gm./1iter of said element, allowing said wool to remain in said aqueous bath at a substantially constant room temperature for a period of time ranging from about 5 to about 10 minutes to cause impregnation of said wool with said solution, removing said wool from said bath and drying said impregnated wool.
  • a polymerized epoxide compound selected from the group consisting of carboxylic acid epoxyalkyl esters, epoxy-alkyl ethers and epoxidized uns

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Epoxy Compounds (AREA)
US593312A 1955-06-23 1956-06-25 Process for making wool resistant to felting and shrinking Expired - Lifetime US2926064A (en)

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DEB36246A DE1009590B (de) 1955-06-23 1955-06-23 Verfahren zum Filz- und Krumpfechtmachen von Wolle

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DE (1) DE1009590B (enrdf_load_html_response)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3285691A (en) * 1963-10-28 1966-11-15 Nathan H Koenig Epichlorohydrin and acid anhydride treatment of wool

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH555929A (enrdf_load_html_response) * 1972-08-08 1974-11-15

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2131145A (en) * 1934-09-15 1938-09-27 Ig Farbenindustrie Ag Process for increasing the reactivity of naturally or artificially shaped articles or materials and product obtained thereby
US2202169A (en) * 1935-01-25 1940-05-28 Ig Farbenindustrie Ag Method of protecting goods containing proteins against insects
US2434562A (en) * 1941-10-17 1948-01-13 Textile Foundation Process of treating animal fibers and product thereof
US2606810A (en) * 1949-09-28 1952-08-12 American Cyanamid Co Treatment of wool-containing textile materials and products thereof
GB709377A (en) * 1951-04-06 1954-05-19 Ciba Ltd Process for treating wool

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1059893A (fr) * 1951-03-29 1954-03-29 Postel Spritzguss Gebr Postel Curseur pour fermeture à curseur

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2131145A (en) * 1934-09-15 1938-09-27 Ig Farbenindustrie Ag Process for increasing the reactivity of naturally or artificially shaped articles or materials and product obtained thereby
US2202169A (en) * 1935-01-25 1940-05-28 Ig Farbenindustrie Ag Method of protecting goods containing proteins against insects
US2434562A (en) * 1941-10-17 1948-01-13 Textile Foundation Process of treating animal fibers and product thereof
US2606810A (en) * 1949-09-28 1952-08-12 American Cyanamid Co Treatment of wool-containing textile materials and products thereof
GB709377A (en) * 1951-04-06 1954-05-19 Ciba Ltd Process for treating wool

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3285691A (en) * 1963-10-28 1966-11-15 Nathan H Koenig Epichlorohydrin and acid anhydride treatment of wool

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GB818162A (en) 1959-08-12

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