US2426770A - Textile finishing composition comprising a methoxymethyl melamine and an aliphatic alcohol having at least eight carbon atoms - Google Patents

Textile finishing composition comprising a methoxymethyl melamine and an aliphatic alcohol having at least eight carbon atoms Download PDF

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Publication number
US2426770A
US2426770A US42995542A US2426770A US 2426770 A US2426770 A US 2426770A US 42995542 A US42995542 A US 42995542A US 2426770 A US2426770 A US 2426770A
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United States
Prior art keywords
water
fabric
weight
melamine
alcohol
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English (en)
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Grim John Marshall
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Wyeth Holdings LLC
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American Cyanamid Co
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Priority to FR964185D priority Critical patent/FR964185A/fr
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US42995542 priority patent/US2426770A/en
Priority to GB200743A priority patent/GB600184A/en
Priority to CH253938D priority patent/CH253938A/de
Application granted granted Critical
Publication of US2426770A publication Critical patent/US2426770A/en
Priority to DEA3405A priority patent/DE874754C/de
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Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]

Definitions

  • This invention relates to the treating and finishing of textiles and textile-forming materials.
  • the invention includes processes for finishing textiles, textile finishing compositions, the preparation of such textile finishing compositions, and textiles of improved properties finished with the compositions and by the processes of the invention.
  • Textile fabrics, yarns, threads and fibers have been heretofore treated with a wide variety of creaseproofing agents, waterproofing agents, materials to prevent shrinking, felting, fulling, etc., lubricants, softening agents, sizes, binding agents and other materials to improve the appearance and feel or hand of the goods.
  • the treatment of textiles for these and similar purposes is known as textile finishing, and the agents employed for this purpose are known as textile finishing agents.
  • the various textile materials which may be treated in accordance with my invention include fibers, thread, yarns, knit and woven cloth, and
  • textile fabrics jute, regenerated cellulose, cellulose esters, cellulose ethers, wool, synthetic wool, silk, synthetic silk and other fibrous materials whether natural or synthesized.
  • textile fabrics jute, regenerated cellulose, cellulose esters, cellulose ethers, wool, synthetic wool, silk, synthetic silk and other fibrous materials whether natural or synthesized.
  • My improved textile finishing process includes the steps of treating textile fabrics such as mentioned above with dispersions of alkylated methylol melamine and a higher aliphatic alcohol followed by drying and curing these resin-forming constituents on the fabric.
  • I may treat the textile fabric with an aqueous dispersion containing approximately 10 parts of methylated methylol melamine and 1.5 parts of octadecyl alcohol followed by an appropriate heat treatment.
  • the improved results which I obtain are due, I believe, to certain chemical reactions which take place during the drying and curing treatment between the alkylated methylol melamine and the higher alcohol.
  • a textile fabric treated with a methylated methylol melamine having a structure such as a W N CHaOCH2 N N 01120 CH3 is subjected to a heat treatment the methylated methylol melamine polymerizes, or cures, in the fabric. Curing of the resin takes place by splitting off one or more molecules of methyl alcohol followed by a molecular rearrangement which favors polymerization. While, as stated before, fabrics so treated have a very marked resistance to shrinking, a good hand, crease-resistance and other important characteristics the fabrics are not particularly water-repellent. This lack of water-resistance is due in part at least to the fact that the polymerized resin molecule has no effective hydrophobic groups available to repel water.
  • the cured resin is fairl easily wetted and water is allowed to penetrate into the interstices of the fabric.
  • a chemical reaction takes place between the' alkylated methylol melamine and higher alcohol which modifies the nature of the cured resin yet does not materially influence the polymerization-mechanism necessary to obtain a permanent water-insoluble, cured resin in the fabric.
  • I may employ any alkylated methylol melamine having at least two alkylated methylol groups, one for reaction with the higher aliphatic alcohol and the other providing a point at which polymerization may proceed.
  • I may, of course, employ alkylated methylol melamines having more than two alkylated methylol groups and ordinarily do so.
  • my invention in its broader aspects is not limited to the use of methylated methylol melamines as illustrated above.
  • Alkylated methylol melamines having short chain alkyl groups of not more than 4 carbon atoms such as ethylated, isopropylated and butylated methylol melamines may also be employed but require greater care in the curing steps, Ethyl alcohol and butyl alcohol split off during the curing steps with greater diificulty and a proper cure is more difiicult to obtain without employing temperatures which might damage the fabric.
  • Methylated methylol melamines which I employ are prepared by known methods.
  • Methylated methylol melamine may, for example, be prepared by reacting 2 to 6 moles of formaldehyde with 1 mole of melamine to form a condensation product believed to be mostly methylol melamine.
  • methylated methylol melamine I intend to include all of these various reaction products containing from 2 to 6 methylated methylol groups per molecule. Excessive polymerization should be avoided during the preparation since the resin is preferably employed'by me in the form of an aqueous dispersion, or solution, and products polymerized excessively tend to be difficultly soluble in water.
  • One-half part by weight of the higher alcohol for each 10 parts by weight of the alkylated methylol melamin will form 'a finishing composition capable of rendering most textile fabrics fairly water-resistant. All the advantages of shrink-resistance, crease-resistance, improved hand, etc. obtained by treatment with methylated methylol melamine alone are of course imparted to the fabric as a result of my treatment whether the proportion -of higher alcohol be either high or low in the finishing composition.
  • the alkylated methylol melamine-higher alcohol composition which I employ in my process is ordinarily, and preferably, applied to the cellulose fabrics in the form of an aqueous dispersion containing from about 2-15% or more of the above materials.
  • These dispersions may be prepared by simply stirring a suitable amount of the higher alcohol dissolved in a solvent such as ethyl alcohol,'isopropyl alcohol, etc. into an aqueous disperson of the alkylated methylol melamine, both solutions being preferably at temperatures of F. to F.
  • Dispersing agents may be used such as sodium isopropyl naphthalene sulfonate, dioctyl sodium sulfosuccinate, ammonium caseinate, gelatine, glue, gum arabic, etc.
  • the preparation of these dispersions is illustrated in greater detail in the specific examples.
  • the dispersions may be applied to the fabrics in various ways known to those in the art; thus, for example, the dried fabrics to be treated may be immersed in the .resin dispersion and then passed through suitable rolls as in a padder or mangle to secure uniform impregnation and to remove excessive resin.
  • the fabric may be impregnated by other methods such as by spraying or with suitable boxes located on the mangle. My invention is not limited to any particular method of impregnating the fabrics and other methods will occur to those skilled in the art.
  • the amount of my alkylatedmethylol mel amine-higher aliphatic alcohol finishing composition which may be applied to fabrics may vary considerably depending upon the nature of the fabric treated and the particular finish desired. Fabrics of wool, silk, cotton, etc. may be rendered water-repellent and substantially resistant to shrinkage by the application of from about 2 to 8% by weight of the resin-forming constituents based on the dry weight of the fabric. Smaller amounts down to 0.5% may be used with less effective results. Larger amounts as for example 8-14% by weight of the fabric will increase the water repellency of the fabric and also impart thereto a high degree of crease-resistance. With particular types of fabrics and to secure particular results it may be desirable to use larger amounts of.
  • my finishing composition up to 30% by weight of the alkylated methylol melamine-higher aliphatic alcohol mixture as based on its weight in the finishing composition. After the fabric has been impregnated it is dried and the fabric heated at elevated temperatures to polymerize the resin.
  • a suitable catalyst may be added to the aqueous finishing composition.
  • Oxalic acid, diammonium hydrogen phosphate and methyl acid pyrophosphate are particularly good for this purpose.
  • other catalysts such as triethanolamine phthalate, zinc chloride, acetic acid, mineral acids such as hydrochloric acid and others may also be used.
  • Other catalysts for the curing of alkylated methylol mel amine resins are know to chemists in the resin art and may be employed.
  • the curing temperatures are in general quite low anad may vary considerably from about 200 F. to about 300 F. with a corresponding reduction in time of cure with increase of temperature.
  • the drying and curing operation is flexible and may be varied to suit the equipment available to the processes. High temperatures of the order of 280 F. to 300 F. will cure the resin to a suitably water-insoluble state in three or four minutes. Where facilities are not available for curing the resin at moderate temperatures within the range of about 240280 F. the fabric after being impregnated with the desired amount of my finishing composition may be framed to width on a pin tenter, dried, batched upon a shell and allowed to stand hot to obtain a total drying and heating time suflicient to dry the cloth and insolubilizing the resin in the fabric. With some fabrics a drying and curing time of two or three hours may be required at 200 F. Drying and curing times will also depend to some extent upon the effectiveness of the particular accelerator employed and upon the nature of the fabric.
  • the fabric After the fabric has been treated as described it should, particularly in the case of woolen goods, be iven a short mild soaping which renders it soft and pliable.
  • the fabric may then be given other usual finishing treatments such as decatizing, brushing, sheering, pressing, etc.
  • My process may be employed with both colored and uncolored goods without appreciably afiecting the color or shade and without damage to the material.
  • Example 1 960 parts by weight of formalin (37% by weight 01-120) and 252 parts by weight of melamine were charged into a reaction vessel fitted with an 9.81-- tator, thermometer, and reflux condenser and arranged so that it could be placed under a. vacuum and heated.
  • the contents of the reaction vessel were heated in one-half hour to a temperature of 62 C. and the pH adjusted to 1.5 with 2 normal NaOH. After heating for another onehalf hour, a vacuum of 28 inches of mercury was applied and the mixture concentrated by removal of water. After 40 minutes heating at approximately 54 C. the heat and vacuum were removed and 1000 parts by weight of methyl alcohol containing enough 2 normal HaPO4 to neutralize the 2 normal NaOH added previously.
  • the mixture at a pH of 6.4 was then heated to distill ofi an azeotropic mixture of methanol and water, anhydrous methanol being continuously added to replace the distillate. After heating in this way for about 6 to 7 hours, one part of the distillate would tolerate parts of toluol and the resin was considered dried. It was then concentrated under a vacuum of 28 inches of mercury to a solids content of approximately 80%.
  • Samples of 80 x 80 cotton percale were then impregnated with this dispersion by the dip and nip process, regulating the take-up so that the fabric contained approximately 11.5% by weight of the methylated methylol melamine-octadecyl alcohol constituents.
  • the impregnated fabric was then dried and cured for seven minutes at 290 F.
  • the treated cloth samples were then given a short soaping for hour at F. in a soap solution, rinsed and dried.
  • Other samples of the treated fabric were soaped at 160 F. in a .5% soap solution for four hours and 6 hours in order to establish the permanency of the water-repellent finish.
  • Still other samples were cleaned in Stoddard solvent for two hours and four hours at room temperatures to determine the stability of the finish to dry-cleaning.
  • the samples were then subjected to a standardized water-repellency test.
  • the water repellency test was conducted as follows: A 6 inch square of the cloth treated with the finishing composition was suspended 10 inches from a horizontal spray nozzle supplied with water at 80 F. under a hydraulic head of exactly 6 feet. The cloth was sprayed for one minute during which time 1.5 gallons of water were discharged through the nozzle. The cloth samples were then dried for 10 seconds, rolled between pieces of absorbent paper to remove surface water, and then weighed. The increase of weight was expressed as percent water absorbed, based on the original dry weight of the cloth. An un- 7 treated sample of the cloth absorbed from 90-100% of its weight of water. The results of these spray tests are as follows:
  • a method of finishing textile fabrics which comprises impregnating the textile fabric with an aqueous dispersion containing 2 to by weight of a mixture of a substantially unpolymerized, water-soluble methoxymethyl melamine containing at least two methoxymethyl groups and an aliphatic alcohol having at least 8 carbon atoms, said aliphatic alcohol being present in the dispersion in amounts corresponding to about 0.5 part to 5.0 parts by weight for each 10 part by weight of methoxymethyl melamine, and thereafter heating the treated textile to insolubilize the resin-forming constituents therein.
  • a method of finishing textile fabrics which comprises impregnating the textile fabric with an aqueous dispersion containing 2 to 15% by weight of a mixture of a substantially unpolymerized, water-soluble methoxymethyl melamine containing at least two methoxymethyl groups and octadecyl alcohol, said octadecyl alcohol being present in the dispersion in amounts corresponding to about 0.5 part to 5.0 parts by weight for each 10 parts by weight of methoxymethyl melamine and thereafter heating the textile fabrics to insolubilize the resin-forming constituents therein.
  • a method of finishing textiles which comprises impregnating the textile fabric withln aqueous dispersion containing 2 to 15% by weight of a; mixture of a substantially unpoly- 5 merized, water-soluble methoxymethyl melamine containing at least two methoxymethyl groups and an aliphatic alcohol having at least 8 carbon atoms, said aliphatic alcohol being present in the dispersion in amounts corresponding to about 10 0.5 to 5.0 parts by weight for each 10 parts by weight of methoxymethyl melamine and curing the resin-forming constituents within the range 200 F. to 300 F. to a water-insoluble state.
  • a textile finishing composition comprising an aqueous dispersion of a substantially unpolymerized, water-soluble methoxymethyl melamine containing at least two methoxymethyl groups and dodecyl alcohol. said dodecyl alcohol being present in the dispersion in amounts corresponding to about 0.5 part to 5.0 parts by weight for.
  • a textile finishing composition comprising an aqueous solution of a water-soluble methoxymethyl melamine containing at least two methaqueous solution of a Water-soluble methoxymethyl melamine containing at least two methoxymethyl groups, said solution having dispersa therein an aliphatic alcohol having at least 8 car bon atoms in amounts of about 0.5-5 part b:
  • a textile finishing composition comprisin; an aqueous solution of a water-soluble methoxy methyl melamine containing at least two meth oxymethyl groups, said solution having disperse therein about 0.5-5 parts by weight of octadec alcohol for each 10 parts of the methoxymeth;
  • a method of finishing textile fabrics whici comprises impregnating the fabric with a com position comprising a dispersion of an aliphati alcohol of at least 8 carbon atoms in an aqueoisolution of a water-soluble methoxymeth5 melamine containing at least two methoxy methyl groups and thereafter heating the im pregnated fabric to insolubilize the resin-form ing constituents therein.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US42995542 1942-02-07 1942-02-07 Textile finishing composition comprising a methoxymethyl melamine and an aliphatic alcohol having at least eight carbon atoms Expired - Lifetime US2426770A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
FR964185D FR964185A (enrdf_load_stackoverflow) 1942-02-07
US42995542 US2426770A (en) 1942-02-07 1942-02-07 Textile finishing composition comprising a methoxymethyl melamine and an aliphatic alcohol having at least eight carbon atoms
GB200743A GB600184A (en) 1942-02-07 1943-02-06 Improvements in or relating to finishing textile fabrics and compositions therefor
CH253938D CH253938A (de) 1942-02-07 1945-06-11 Beständiges Mittel zum Behandeln von Textilien.
DEA3405A DE874754C (de) 1942-02-07 1950-09-09 Praeparat und Verfahren zum Appretieren von Textilien

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US42995542 US2426770A (en) 1942-02-07 1942-02-07 Textile finishing composition comprising a methoxymethyl melamine and an aliphatic alcohol having at least eight carbon atoms

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US2426770A true US2426770A (en) 1947-09-02

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US (1) US2426770A (enrdf_load_stackoverflow)
CH (1) CH253938A (enrdf_load_stackoverflow)
DE (1) DE874754C (enrdf_load_stackoverflow)
FR (1) FR964185A (enrdf_load_stackoverflow)
GB (1) GB600184A (enrdf_load_stackoverflow)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2509174A (en) * 1947-05-22 1950-05-23 Monsanto Chemicals Process of waterproofing textile fabrics
US2555277A (en) * 1945-08-13 1951-05-29 American Cyanamid Co Composition for shrinkproofing and mothproofing woolen textiles
DE921300C (de) * 1948-10-10 1954-12-13 Cassella Farbwerke Mainkur Ag Verfahren zur Veredelung von Fasermaterial
US2715078A (en) * 1948-10-27 1955-08-09 Monsanto Chemicals Process of impregnating cellulosic material with thermosetting resin
US2835641A (en) * 1949-08-11 1958-05-20 Ciba Ltd Aqueous emulsions for the preparation of water repellent dressings and process of treating fibrous materials therewith
US2971931A (en) * 1956-05-22 1961-02-14 American Cyanamid Co Textile treatment with novel aqueous dispersions to achieve flame-resistant and water-repellant finishes
US2971930A (en) * 1956-05-22 1961-02-14 American Cyanamid Co Textile treatment with novel aqueous dispersion to achieve water-repellent finishes
US2971929A (en) * 1956-05-22 1961-02-14 American Cyanamid Co Textile treatment with novel aqueous dispersions to achieve flame-resistant and water-repellant finishes
US3059027A (en) * 1958-11-18 1962-10-16 Rohm & Haas Process of producing alkylated polymethylol aminoplast condensates
US3061474A (en) * 1959-05-25 1962-10-30 Exxon Research Engineering Co Process for treating cellulosic fabric, composition therefor and fabric resulting therefrom
US3087837A (en) * 1959-05-06 1963-04-30 American Cyanamid Co Process for treating cellulose containing textile material with an alkylated melamine-formaldehyde reaction product
US3129226A (en) * 1958-10-13 1964-04-14 Allied Chem Solutions of melamine-formaldehyde reaction products and processes for their production
US3261835A (en) * 1959-01-19 1966-07-19 Monsanto Co Polysubstituted amino-s-triazines
US3267099A (en) * 1962-04-09 1966-08-16 Du Pont 2-alkoxy and mercapto-4, 6-bis alkoxy alkyl amino-s-triazines
US3303015A (en) * 1960-12-27 1967-02-07 Monsanto Co Herbicidal composition and method
US5580609A (en) * 1991-05-20 1996-12-03 Alliedsignal Inc. Process of making amide melamine wax coated polymeric monofilaments

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL113592C (enrdf_load_stackoverflow) * 1952-06-04 1900-01-01

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB486577A (en) * 1936-10-28 1938-05-30 Arthur George Bloxam Manufacture of condensation products from aminotriazines
US2197375A (en) * 1938-07-27 1940-04-16 Joseph K Dafnis Transfer apparatus for railway cars

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB486577A (en) * 1936-10-28 1938-05-30 Arthur George Bloxam Manufacture of condensation products from aminotriazines
US2197375A (en) * 1938-07-27 1940-04-16 Joseph K Dafnis Transfer apparatus for railway cars

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2555277A (en) * 1945-08-13 1951-05-29 American Cyanamid Co Composition for shrinkproofing and mothproofing woolen textiles
US2509174A (en) * 1947-05-22 1950-05-23 Monsanto Chemicals Process of waterproofing textile fabrics
DE921300C (de) * 1948-10-10 1954-12-13 Cassella Farbwerke Mainkur Ag Verfahren zur Veredelung von Fasermaterial
US2715078A (en) * 1948-10-27 1955-08-09 Monsanto Chemicals Process of impregnating cellulosic material with thermosetting resin
US2835641A (en) * 1949-08-11 1958-05-20 Ciba Ltd Aqueous emulsions for the preparation of water repellent dressings and process of treating fibrous materials therewith
US2835639A (en) * 1949-08-11 1958-05-20 Ciba Ltd Aqueous emulsions for the preparation of water repellent dressings and process of treating fibrous materials therewith
US2971929A (en) * 1956-05-22 1961-02-14 American Cyanamid Co Textile treatment with novel aqueous dispersions to achieve flame-resistant and water-repellant finishes
US2971930A (en) * 1956-05-22 1961-02-14 American Cyanamid Co Textile treatment with novel aqueous dispersion to achieve water-repellent finishes
US2971931A (en) * 1956-05-22 1961-02-14 American Cyanamid Co Textile treatment with novel aqueous dispersions to achieve flame-resistant and water-repellant finishes
US3129226A (en) * 1958-10-13 1964-04-14 Allied Chem Solutions of melamine-formaldehyde reaction products and processes for their production
US3059027A (en) * 1958-11-18 1962-10-16 Rohm & Haas Process of producing alkylated polymethylol aminoplast condensates
US3261835A (en) * 1959-01-19 1966-07-19 Monsanto Co Polysubstituted amino-s-triazines
US3087837A (en) * 1959-05-06 1963-04-30 American Cyanamid Co Process for treating cellulose containing textile material with an alkylated melamine-formaldehyde reaction product
US3061474A (en) * 1959-05-25 1962-10-30 Exxon Research Engineering Co Process for treating cellulosic fabric, composition therefor and fabric resulting therefrom
US3303015A (en) * 1960-12-27 1967-02-07 Monsanto Co Herbicidal composition and method
US3267099A (en) * 1962-04-09 1966-08-16 Du Pont 2-alkoxy and mercapto-4, 6-bis alkoxy alkyl amino-s-triazines
US5580609A (en) * 1991-05-20 1996-12-03 Alliedsignal Inc. Process of making amide melamine wax coated polymeric monofilaments
US5709942A (en) * 1991-05-20 1998-01-20 Alliedsignal Inc. Product and process improvement of coated polymeric monofilament

Also Published As

Publication number Publication date
FR964185A (enrdf_load_stackoverflow) 1950-08-08
GB600184A (en) 1948-04-02
DE874754C (de) 1953-04-27
CH253938A (de) 1948-04-15

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