US3057675A - Process for finishing fibrous materials, and compositions for use therein - Google Patents

Process for finishing fibrous materials, and compositions for use therein Download PDF

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Publication number
US3057675A
US3057675A US825642A US82564259A US3057675A US 3057675 A US3057675 A US 3057675A US 825642 A US825642 A US 825642A US 82564259 A US82564259 A US 82564259A US 3057675 A US3057675 A US 3057675A
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parts
triazine
fibrous material
water
carbon atoms
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US825642A
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Hiestand Armin
Maeder Arthur
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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
    • 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
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358—Triazines
    • 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
    • Y10S8/21—Nylon

Definitions

  • This invention relates to a process for imparting a finish to fibrous materials, particularly textile materials and to compositions used in said process.
  • Fibrous materials which can be advantageously finished by the aforesaid process include animal fibers such as wool or silk, semi-synthetic fibers such as cellulose acetate fibers, and fully synthetic fibers such as polyamide fibers, for example those derived from e-caprolactam or from adipic acid and hexamethylenediamine.
  • the process has proved particularly advantageous when applied to cellulose-containing fibers such as linen or cotton and to fibers consisting of regenerated cellulose, such as viscose rayon or staple fiber.
  • the triazine compounds employed in the present process comprise at least one 1,3,5-triazine ring. There is directly attached to the said triazine ring at least one halogen atom, and at least one substituent comprising a hydrocarbon radical containing more than 7 carbon atoms.
  • the said hydrocarbon radical may be attached directly to the said ring but preferably is linked thereto through a bridge member containing or consisting of at least one hetero atom.
  • the 1,3,5-triazine ring may be substituted in 2,4,6-position by (a) two halogen atoms and one substituent containing the hydrocarbon radical of more than 7 carbon atoms,
  • Chlorotriazine compounds are preferably employed.
  • the hydrocarbon radical preferably contains 12 to 22 carbon atoms. It may be branched or unbranched, saturated or unsaturated. In addition, it may be attached to the triazine ring through, for example, a sulfur atom, an oxygen atom or, preferably, through a nitrogen atom.
  • the substituent corresponds, for example to the formula:
  • R-ITI- in which R represents an aliphatic hydrocarbon radical containing at least 8 carbon atoms, and R an alkyl radical, which may also contain 8 or more carbon atoms, or a hydrogen atom.
  • the monoor dichlorotriazine compounds containing the radical of such an aliphatic amine preferably correspond to the formula:
  • R represents an aliphatic hydrocarbon radical, preferably an alkyl radical containing from 16 to 22 carbon atoms, R a hydrogen atom or an aliphatic hydrocarbon radical, and X a chlorine atom or an amino group, for example an H N-group or a group of the formula:
  • atoms may alternatively be attached to the triazine ring through a bridge containing more than one hetero atom,
  • R has the meaning assigned to it above, and A represents an alkylene radical, for example an ethylene or propylene radical, or a phenylene radical.
  • the triazine compound contains, in addition to the halogen atom and the substituent containing the aliphatic hydrocarbon radical of 8 or more carbon atoms, a further substituent of any form, for example a hydroxyl group, an amino group, an alkoxy group, e.g. a methoxy group, an aryloxy group, e.g. a phenoxy group or an aryl-mercapto group, e.g. a phenyl-mercapto group, optionally further substituted in the aryl nuclei, or a radical attached directly to the triazine nucleus.
  • a further substituent of any form for example a hydroxyl group, an amino group, an alkoxy group, e.g. a methoxy group, an aryloxy group, e.g. a phenoxy group or an aryl-mercapto group, e.g. a phenyl-mercapto group, optionally further substituted in the aryl nu
  • R, R R and R each represent a bivalent aliphatic hydrocarbon radical, the radical R containing at least 8 carbon atoms, and n, p, q, and r each represent a whole number of at most 2.
  • the compounds of the Formula VIII in addition to the high molecular radical R may contain one, two or three further aliphatic hydrocarbon radicals and three, two or one hydrogen atoms bound to the nitrogen atoms.
  • the monochloro- 1,3,5-triazine compounds may preferably correspond to the formula in which at least one and at the most two Rs represent alkyl radicals containing 16 to 22 carbon atoms and the remaining Rs represent hydrogen atoms.
  • the triazine compounds employed in the present invention may be prepared, by methods known per se from the literature, from cyanuric halides, such as cyanuric bromide or preferably cyanuric chloride and alcohols, mercapta-ns, phenols, thiophenols or amines.
  • cyanuric halides such as cyanuric bromide or preferably cyanuric chloride and alcohols, mercapta-ns, phenols, thiophenols or amines.
  • Compounds containing hydrocarbon radicals directly attached to the triazine ring are obtained by reacting cyanuric halide with alkyl-, cycloalkyl-, aralkylor aryl-magnesium halides.
  • Compounds of Formula II in which X represents a chlorine atom are preferably prepared by condensation of cyanuric chloride with one or more amines of the formula:
  • R and R have the meanings assigned to them above, in the molecular ratio 1:1, in organic solvents at low temperature.
  • the impregnation of the fibrous material is effected with a liquid-containing preparation which contains the triazine compound.
  • a liquid-containing preparation which contains the triazine compound.
  • solutions of the compounds in inert organic solvents i.e. those not reacting with halogen atoms of the triazine compounds
  • inert organic solvents such as carbon tetrachloride, dichloroethane, methyl ethyl ketone, benzene, xylene, perchloroethylene and petroleum hydrocarbon
  • the impregnating liquid may be an aqueous emulsion of the triazine compound.
  • the triazine compounds are not liquid at room temperature, so that to formulate the emulsions it is preferable to dissolve the triazine compound in an inert solvent, for example chlorobenzene or a dichlorobenzene, and to emulsify the resulting solution in water.
  • an inert solvent for example chlorobenzene or a dichlorobenzene
  • only a small quantity of solvent is generally required in relation to the quantity of the triazine compound, so that the mixture of triazine compound and 501- vent is less a solution in the usual sense than a melt.
  • emulsifiers may be employed but in order to avoid saponification of the triazine compounds (exchange of halogen atoms for hydroxyl groups) it is important that the emulsifiers should not be more than at most mildly alkaline.
  • Either ionic or non-ionic emulsifiers may be employed.
  • the latter class includes, in particular, polyglycol compounds, for example polyglycol ethers of aliphatic alcohols of high molecular weight.
  • water-soluble poly vinyl alcohol or a polypeptide-containing substance, such as gelatine may be included as a thickening agent, preferably in addition to a polyglycol compound.
  • agents for the finishing of the fibrous materials may be added to the aforesaid preparations, for example dressing agents, such as agents which are capable of exerting a similar action to the triazine compounds.
  • Examples are agents capable of imparting a soft handle to the textile material or water-repelling agents such as wax-like substances, e.g. paraffin wax, chloro-paraffin waxes, or a fusable polyalkylene such as polymerized ethylene, propylene or isobutylene.
  • the wax-like substances may be simply added to solutions of the triazine compounds in organic solvents or, when the preparations are emulsions, they may be dissolved in the organic liquid of the emulsion together with the triazine compound. They may also be dissolved in an organic solvent separate- 1y from the triazine compounds, whereby emulsions comprising two different discontinuous phases may be produced.
  • the triazine compound content of the preparations may vary within wide limits.
  • preparations may be directly prepared in which the concentration is, for example, from 3 to 10 parts of triazine compound in parts of the preparation.
  • the fibrous materials may be impregnated in any usual manner, for example by dipping, spraying or coating, advantageously at room temperature or at most at a slightly elevated temperature. It is particularly desirable to impregnate woven fabrics with the preparations on :1 padding machine.
  • the impregnation is followed, if desired after intermediate drying at room temperature or at most at slightly elevated temperature, by treatment with an acid-binding medium, with the object of inducing chemical reaction between the halogenotriazine compound and the fibrous material, so that the triazine compound becomes attached (in homoeopolar fashion) to the fibrous materinl, for example to the oxygen atoms of a cellulosic fibrous material.
  • This treatment may advantageously be carried out with dilute aqueous sodium carbonate solution. Temeratures of at most 30 to 40 C. are generally sufiicient for the treatment, e.g. in the case where dichlorotriazine compounds are employed.
  • the treatment of the fibrous materials by the process of the present invention generally produces a water-repelling efiect and at the same time imparts a soft handle to the fibrous material.
  • EXAMPLE 1 (A) Preparation of the triazine c0mpozmd.-IO0 parts (0.362 mol.) of a commercial stearylamine containing 93% of octadecylamine, 6% of hexadecylamine and 1% of octadecenylamine are dissolved in 2,000 parts of acetone at 50 to 60. On cooling to 2 to 5 with stirring, a fine suspension is obtained, to which is slowly added a similarly prepared suspension of 67 parts (0.52 mol.) of cyanuric chloride and 320 parts of acetone. It is to be noted that the temperature of the mixture should not exceed 5.
  • any other primary or secondary alkylamine of relatively high molecular weight may be employed.
  • a reaction product which, after recrystallization from alcohol, gives about 191 parts of a well-crystallized substance melting at 126-135
  • Unsaturated amines such as octodecenylamine (oleylamine) or an amine mixture prepared from coconut oil, do not give any Well-crystallized products.
  • a corresponding melt consisting of equal parts of triazine derivative and parafiin wax having a melting point of 5052 may be employed.
  • EXAMPLE 2 (A) Preparation of the triazine c0mp0ima's.-(i) In a stirrer-type vessel provided with a dropping funnel and a thermometer, a suspension of 67 parts of cyanuric chloride in 320 parts of acetone is cooled to 0, and a solution of 100 parts of commercial stearylamine (molecular weight 276) in 2,000 parts of acetone is added drop-wise thereto in about 1 hour, the temperature being maintained between 2 and +2.
  • the temperature is allowed to rise to +10 and a solution of 19.2 parts of anhydrous sodium carbonate in 170 parts of water is added in the course of about 50 to 60 minutes, so that the temperature can be maintained between 10 and The mixture is thereafter allowed gradually to heat up to room temperature and is further stirred for 3 to 4 hours.
  • the precipitated white powder is separated off and the acetone solution is evaporated to dryness in vacuo at a temperature not exceeding 40.
  • the residue is emulsified in 1000 parts of water at about 50, suction-filtered and washed out with 2 l000 parts of cold Water on the suction filter. It is then dried in vacuo at 50 until its weight remains constant.
  • EXAMPLE 3 (A) Preparation of the triazine c0mp0und.-In a stirrer-type vessel having a capacity of 5,000 parts by volume and comprising a thermometer and a dropping funnel, a suspension of 67 parts of cyanuric chloride in 320 parts of acetone is cooled to 0, and there is added dropwise thereto in about 4550 minutes a solution of 113 parts of a commercial mixture of primary alkylamines, containing about 10% of stearylamine, 55% of arachidylamine and 35% of behenylamine, in 2,000 parts of acetone, the temperature being maintained between 2 and +2.
  • EXAMPLE 4 (A) Preparation of the triazine c0mpound.In a stirrer-type vessel having a capacity of 2,000 parts by volume and provided with a reflux condenser and a thermometer, a suspension of 60 parts of 2-ocetadecylamino-4,6-dichloro-1,3,5-triazine and 39.7 parts of commercial stearylamine (molecular weight 276) in 1,500 parts of acetone and 500 parts of benzene is stirred for 5 hours at boiling temperature (about 55) under reflux. The mixture is thereafter cooled to room temperature and suction-filtered. The crude product is recrystallized in the moist state from 500 parts of benzene, cooled to +8 and immediately filtered off.
  • Emulsions are prepared, employing the triazine compounds described in Examples 2, 3 and 4.
  • the procedure indicated under B in Example 2 is followed, but 30 parts of a gelatine solution are employed instead of the polyvinyl alcohol solution, and 1 part of sodium borate is added to the 26 parts of water at 70 which are finally to be added.
  • Very fine emulsions sometimes in the form of pastesare obtained, which can be diluted with Water.
  • EXAMPLE 6 Highly colloidal emulsions suitable for water-proofing and for the production of a soft handle in accordance with the method of Example 1C are prepared by the method of Example 1B but replacing the polyvinyl alcohol by the same quantity of a 10% gelatine solution, and employing for the emulsification a melt consisting of 18 parts of triazine compound (see Example 1A) and 18 parts of a polyethylene glycol having a molecular Weight of 300, the formed emulsion thereafter being immediately diluted with 200 parts of water at 80.
  • EXAMPLE 7 In an open-stirrer type vessel, 3 parts of an emulsifier obtained by the addition of 80 mol. of ethylene oxide to 1 mol. of oleyl alcohol, and 1.2 parts of a condensation product of naphthalene sulfonic acid and formaldehyde, neutralized with aqueous sodium hydroxide solution, are heated at 80-85 with parts of a 10% gelatine solution. 9.5 parts of hot water are added, and 36 parts of a melt at 98 to 100, consisting of 12 parts each of chlorobenzene, polyethylene and the compound (2- dialkylaminol,6-dichloro-1,3,5-triazine, prepared as in Example 1) are slowly poured in. The melt is rapidly absorbed with formation of an emulsion. 26 further parts of water at to are thereafter added, and the emulsion is homogenised. A highly colloidal emulsion is obtained, which is thereafter diluted with warm water to working concentration.
  • Cotton poplin treated with such an emulsion in accordance with Example 1C, exhibits a pleasant soft handle.
  • a process for imparting water-repellency to cellulosic fibrous material which comprises impregnating the fibrous material with an aqueous emulsion containing polyvinyl alcohol and a 1,3,5-triazine compound of the formula in which R, R R and R each represent a bivalent aliphatic hydrocarbon radical which contains at least 8 and at most 22 carbon atoms, and n, p, q and r each represent a Whole number of at the most 2, and fixing the triazine compound on the cellulosic fibers by treatment with an acid binding agent and subsequent dry heat treatment.
  • a process for imparting water-repellency to cellulosic fibrous material which comprises impregnating the fibrous material with an aqueous emulsion containing parafiin wax and a 1,3,5-triazine compound of the formula in which R, R R and R each represent a bivalent aliphatic hydrocarbon radical which contains at least 8 and at most 22 carbon atoms, and n, p, q and r each represent a whole number of at the most 2, and fixing the triazine compound on the cellulosic fibers by treatment with an acid binding agent and subsequent dry heat treatment.
  • a process for imparting water-repellency to cellulosic fibrous material which comprises impregnating the fibrous material with an aqueous emulsion containing chloroparafin Wax and a 1,3,5-triazine-compound of the formula in which R, R R and R each represent a bivalent aliphatic hydrocarbon radical which contains at least 8 and at most 22 carbon atoms, and n, p, q and r each represent a whole number of at the most 2, and fixing the triazine compound on the cellulosic fibers by treatment with an acid binding agent and subsequent dry heat treatment.
  • a process for imparting water-repellency to cellulosic fibrous material which comprises impregnating the fibrous material with an aqueous emulsion containing a fusible polyethylene and a 1,3,5-triazine compound of the formula in which R, R R and R each represent a bivalent aliphatic hydrocarbon radical which contains at least 8 and at most 22 carbon atoms, and n, p, q and r each represent a whole number of at the most 2, and fixing the triazine compound on the cellulosic fibers by treatment with an acid binding agent and subsequent dry heat treatment.
  • a process for imparting water-repellency to cellulosic fibrous material which comprises impregnating the fibrous material with an aqueous emulsion containing parafiin wax and a 1,3,5-triazine compound of the formula in which at least one and at the most two Rs represent alkyl radicals containing from 16 to 22 carbon atoms each and the remaining Rs represent hydrogen atoms, and fixing the triazine compound on the cellulose fibers by treatment with an acid binding agent and subsequent dry heat treatment.
  • An aqueous emulsion for imparting water-repellency to cellulosic fibrous material which contains in a finely dispersed state a 1,3,5-triazine compound of the formula in which R, R R and R each represent a bivalent aliphatic hydrocarbon radical which contains at least 8 and at the most 22 carbon atoms, and n, p, q and r each represent a whole number of at the most 2.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US825642A 1958-07-24 1959-07-08 Process for finishing fibrous materials, and compositions for use therein Expired - Lifetime US3057675A (en)

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BE (1) BE580952A (is")
CH (1) CH351574A (is")
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3508858A (en) * 1966-01-11 1970-04-28 Bemberg Spa Process and product for improving the textile characteristics of natural and synthetic fibers and fibers obtained thereby
US3644253A (en) * 1969-04-09 1972-02-22 Ciba Ltd Aqueous emulsions
WO1985004200A1 (en) * 1984-03-19 1985-09-26 Polyrand Ab A method for treatment of cellulose fibres and production of composite materials of the treated cellulose fibres in combination with resins
US4568421A (en) * 1982-10-23 1986-02-04 Bayer Aktiengesellschaft Monofluorotriazinyl compounds, processes for their preparation and their use as sizing agents

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL296874A (is") * 1962-08-22
DE19516963A1 (de) * 1995-05-12 1996-11-14 Stockhausen Chem Fab Gmbh Verfahren zur Behandlung von Häuten, Fellen, Ledern und Pelzen mit Tensiden zur Verbesserung der Hydrophobierwirkung und zur Angleichung qualitativ unterschiedlichen wet-blue-Materials

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1886480A (en) * 1929-04-11 1932-11-08 Chem Ind Basel Dyestuffs containing cellulose residues and process of making same
US2275593A (en) * 1938-09-03 1942-03-10 Pittsburgh Piate Glass Company Method of cleaning and disinfecting fibrous material
US2385765A (en) * 1941-08-30 1945-09-25 American Cyanamid Co Textile finishing
US2892674A (en) * 1955-05-27 1959-06-30 Ici Ltd Treatment of cellulosic materials

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1886480A (en) * 1929-04-11 1932-11-08 Chem Ind Basel Dyestuffs containing cellulose residues and process of making same
US2275593A (en) * 1938-09-03 1942-03-10 Pittsburgh Piate Glass Company Method of cleaning and disinfecting fibrous material
US2385765A (en) * 1941-08-30 1945-09-25 American Cyanamid Co Textile finishing
US2892674A (en) * 1955-05-27 1959-06-30 Ici Ltd Treatment of cellulosic materials

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3508858A (en) * 1966-01-11 1970-04-28 Bemberg Spa Process and product for improving the textile characteristics of natural and synthetic fibers and fibers obtained thereby
US3644253A (en) * 1969-04-09 1972-02-22 Ciba Ltd Aqueous emulsions
US4568421A (en) * 1982-10-23 1986-02-04 Bayer Aktiengesellschaft Monofluorotriazinyl compounds, processes for their preparation and their use as sizing agents
US5143791A (en) * 1984-03-09 1992-09-01 Polyrand AB and Polycell Kompositer Method for treatment of cellulose fibres and production of composite materials of the treated cellulose fibres in combination with resins
WO1985004200A1 (en) * 1984-03-19 1985-09-26 Polyrand Ab A method for treatment of cellulose fibres and production of composite materials of the treated cellulose fibres in combination with resins
JPS61502968A (ja) * 1984-03-19 1986-12-18 ポリイランド・アクチボラグ セルロ−ス繊維の処理方法および処理されたセルロ−ス繊維と樹脂とを組合せた複合材料

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FR1235674A (fr) 1960-07-08
CH351574A (de) 1961-01-31
DE1175198B (de) 1964-08-06
BE580952A (is")

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