US2357273A - Textile finishing - Google Patents

Textile finishing Download PDF

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US2357273A
US2357273A US434349A US43434942A US2357273A US 2357273 A US2357273 A US 2357273A US 434349 A US434349 A US 434349A US 43434942 A US43434942 A US 43434942A US 2357273 A US2357273 A US 2357273A
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parts
weight
methylol melamine
textile
fabric
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US434349A
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Jack T Thurston
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Wyeth Holdings LLC
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American Cyanamid Co
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Priority to BE475511D priority Critical patent/BE475511A/xx
Priority to NL69462D priority patent/NL69462C/xx
Priority to LU28759D priority patent/LU28759A1/xx
Priority to US434349A priority patent/US2357273A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to GB1701/43A priority patent/GB607950A/en
Application granted granted Critical
Publication of US2357273A publication Critical patent/US2357273A/en
Priority to CH263255D priority patent/CH263255A/de
Priority to ES0179109A priority patent/ES179109A1/es
Priority to FR950928D priority patent/FR950928A/fr
Priority to DEA3493A priority patent/DE864986C/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • 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
    • Y10T442/2352—Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric
    • 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
    • Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2385—Improves shrink resistance
    • 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
    • Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics

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.
  • -It is a principal object of the present invention to provide textile finishing compositions and methods for their preparation and application to textiles, which compositions and methods will produce finished textiles having a greatly improved water resistance, a more desirable hand, crease resistance, a very much reduced tendency for shrinking and other desirable improvements which will be apparent from the description which follows: Other important objects will appear hereinafter.
  • the various textile materials which may be treated in accordance with my invention include fibers, thread, yarns, knit and woven cloth and other fabricated materials of cotton, linen, hemp, jute, regenerated cellulose, cellulose esters, cellulose ethers, wool, synthetic wool, silk, synthetic silk and other fibrous materials whether natural or synthesized.
  • textile fabrics all of these various textile-forming materials and structures containing the same will be referred to as textile fabrics.
  • My improved textile finishing process includes the steps of treating textile fabrics such as mentioned above with dispersions containing alkylated methylol melamine together with certain (1 Company,
  • the methylated methylol melamine polymerizes, or cures, in the fabric.
  • Curing of the resin probably takes place by splitting off one or more molecules of methyl alcohol followed by a molecular rearrangement which favors polymerization.
  • 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 efiective hydrophobic groups available to repel water. In other words, the cured resin is fairly easily wetted and water is allowed to penetrate into the interstices of the fabric.
  • any compound having a hydrophobic alkyl radical of at least 7 carbon atoms and containing a nitrogen atom having attached thereto an acidic group can be employed in conjunction with alkylated methylol melamines for textile finishing.
  • Combination between the compound containing th acidic nitrogen atom, which is designated herein as an amido group, and the alkylated methylol melamine is brought about under the conditions hereinafter described by means of a reactive hydrogen present on the amido group or one substituent such as an alkylol radical attached thereto.
  • the preferred nitrogen-containing compounds of my invention are those of the formula Z H's-LR in which Y is a member of the group consisting of hydrogen and unsubstituted or substituted alkylol radicals, such as methylol or ethylol radicals, Z is a member of the group consisting of oxygen and sulfur, and x and R are members of the group consisting of hydrogen, non-functional substituents, and radicals containing alkyl hydrophobe groups of at least 7 carbon atoms, it being understood that in all cases at least one X or R contains a hydrophobe alkyl radical of at least '7 carbon atoms.
  • Y is a member of the group consisting of hydrogen and unsubstituted or substituted alkylol radicals, such as methylol or ethylol radicals
  • Z is a member of the group consisting of oxygen and sulfur
  • x and R are members of the group consisting of hydrogen, non-functional substituents, and radicals
  • M is the residue of methylated methylol melamine and R is a higher alkyl radical.
  • Another class of derivatives of aliphatic amides which can b reacted with methylated methylol melamines on the fiber are those corresponding to the formula HO.(CRR ),.NH.COR', where R and R. are hydrogen or alkyl groups and n is a whole number greater than one.
  • R and R. are hydrogen or alkyl groups and n is a whole number greater than one.
  • G is a coupling linkage of the group CH2- and CH2O(CR R )n-, R and R being members of the group consisting of hydrogen and alkyl radicals; n is a small whole number, and M, X, Z and. R are as previously defined.
  • At least one of the short chain groups of the methylated methylol melamine is replaced with a group containing in X or R, or both, one or more long chain hydrophobic alkyl groups.
  • the product also contains in the melamine nucleus at least one methoxy methyl group which at the temperature of the curing process can split ofl methanol allowing a molecular rearrangement to take place with subsequent polymerization with other alkylated methylol melamine molecules.
  • amido compound having the long chain alkyl group which replaces the short chain alkyl group is not split off at the temperature of the curing process and hence the long chain alkyl radical remains as a part of the resin in which it acts to render the resin itself hydrophobic.
  • my invention in its broader aspects is not limited to the use of methylated methylol melamines as illustrated above.
  • Alkylated methylol melamines having short alkyl groups of not more than four 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 ofl during the curing steps with greater difllculty and a proper cure is more difllcult to obtain without employing temperatures which might damage the fabric.
  • the alkylated 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. This product is then reacted with 2 to 6 moles of methanol whereby methylated methylol melamine is formed.
  • a very large number of nitrogen-containing compounds having the characteristics set forth above are suitable for use with alkylated methylol melamines in my textile finishing composition.
  • the preferred class of compounds of this type are for example, the amides of monocarboxylic acids which, in the general formula X is hydrogen and R is an alkyl radical of at least seven carbonatoms, such as, for example, caprylamide, capramide, lauramide, myristamide, palmitamide, stearamide, di-n-octyl-acetamide, oleic acid amide, linoleic acid amide and ricinoleic acid amide.
  • amides of the same general formula, but in which X is an alkyl group may be employed.
  • Such compounds are, for example, N-methylstearamide, N-ethylstearamide, N-ethyllauramide, N-isopropylstearamide, N-2-ethylhexylstearamide and the like.
  • Amides of the general formula above in which H is replaced with an alkylol group such as methylol stearamide, methylol lauramide, ethanol stearamide and others of this class may also be employed.
  • Compounds may also be employed having the general formula x LLB in which X is a cyano radical as for example, lauroyl cyanamide, stearoyl cyanamide, or an alkylene nitrile (-CR'RCEN) radical when using compounds such as, di(octyDcyanacetamide, di(lauryDcyanacetamide, di(stearyl) cyanacetamide, N-p-cyanethyllauramide, etc.; or a carbamyl radical, as in the case of stearoyl urea; or thiocarbamyl radicals, as when using N- myristyl thiourea; or a substituted carbamyl radical where R is an alkyl or aryl radical, as when N-.
  • X is a cyano radical as for example, lauroyl cyanamide, stearoyl cyanamide, or an alkylene nitrile (-CR'RCEN) radical when using compounds such as,
  • X may also be an aryl or alkaryl radical as when using stearanilide, a stearotoluidide, a stearoxylidide and N-benzyl stearamide and similar compounds with alkylated methylol melamine in my finishing composition.
  • R be an aliphatic radical of at least 7 carbon atoms as in the above examples, if the long chain alkyl hydrophobic group is provided elsewhere in the compound.
  • R is a small alkyl group and X is a long chain alkyl radical.
  • Other acid amides of this type may, of course, be employed such-as N-acetyloctadecyl amine, N-acetyldodecyl amine, N-acetyl z-ethyl-hexylamine and others oi! similar character.
  • the urethanes are also examples of nitrogencontaining compounds falling within the purview of my invention and have been employed melamines with very satisfactory results. These compounds are esters of carbamic'acid and have the general formula n-l r-lL-a in which R is an alkoxy radical containing at least 7 carbon atoms. Examples of urethanes which may be employed are octyl carbamate, decyl carbamate, dodecyl carbamate, tetradecyl carbamate, hexyldecyl carbamate, octadecyl carbamate, etc.
  • alkylated methylol melamines in my textile finishing composition and among these may be mentioned lauroyl dicyandiamide and stearoyl dicyandiamide in which case X in the general formula is a cyanoguanyl radical -(ILJNHCN Compounds such as N-methylstearamide acetate in which X is a methoxy acetyl radical may also be employed.
  • X in the general formula is a nitro radical and R is an alkoxy radical.
  • Mono and diacyl substituted ammelines and melamines such as dioctanoyl ammeline, di-
  • monocarboxylic acids my invention is by no means limited thereto since compounds may also be used such as di(octyDoxamide, di(octyDsuccinamide, di(dodecyDsuccinamide, di(tetradecyl) succinamide, di (octadecyl) succinamide, di- (octadecyl) adipamide, di(octadecyl) pimelamide, di(octadecyDsuberamide, and di(octadecyl)sebacamlde, etc. in which both substituents may be attached to the same nitrogen atom or each nitrogen atom may contain one substituent.
  • succinamic acid esters such as the dodecyl esters of succinamic acid, the octadecyl ester of succinamic acid, the octadecyl ester of adipamic acid, etc.
  • Amides of cycloalkyl, aryl by me in conjunction with alkylated methylol andaralkyl carboxylic acids such as cyclqhexyl acetic acid, benzoic acid and phenyl acetic acid which contain a long chain hydrophobe alkyl radical mayalso beemployed in my finishing composition.
  • Other types of compounds falling within the purview of my invention which.
  • alkylated methylohmelamine may be used with alkylated methylohmelamine to produce textile finishing compositions
  • the N-acylated and N-carbalkoxylated urethanes such as N-lauroyl ethyl urethane, and N-carbethoxylaurylurethane, ethyl- N-lauroylcarbamate and lauryl N -carbethoxycarbamate.
  • Y is hydrogen or a methylol radical
  • Z is oxygen or sulfur
  • X may be a non-functional radical such as hydrogen, alkyl, alkylol, cyano, allnvlenenitrile, carbamyl, substituted carbamyl, thlocarbamyl, aryl, cyanoguanyl, alkoxy-acetyl,
  • B. may be an alkyl, alkoxy, oycloalkyl, aryl or aralkyl radical.
  • Such compounds other than those specifically described above are, for example, methyl N-tetradecyl methylsulfonamide, N-tetradecyl phenylsulfonamide, p-lauroyl phenylsulfonamide, N-p-lauramidophenylsulfonamide and the like.
  • acidic groups other than the carbonyl group are effective in activating the hydrogen or methylol radical attached to the amido nitrogen.
  • this amido compound may be used with, however, a decrease in the water resistance of the treated fabric.
  • Onehalf part by weight of the amido compound for each 10 parts by weight of the alkylated methylol melamine will form a finishing composition capable of rendering most textile fabrics fairly waterresistant. All the advantages of shrink resistance, crease-resistance, improved hand, etc., obtained by methylated methylol melamine alone, of course, are imparted to the fabric as a result of my treatment whether the proportion of higher aliphatic amido compound be high or low in the finishing composition.
  • the alkylated methylol melamine-higher aliphatic amido compound composition which I employ in my process is ordinarily, and preferably, applied to the 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 amido compound dissolved in a solvent such as ethyl alcohol, isopropyl alcohol, alkyl ether of ethylene glycol, etc. into an aqueous dissolutions being preferably at temperaturesof 80 F. to 140 F.
  • a solvent such as ethyl alcohol, isopropyl alcohol, alkyl ether of ethylene glycol, etc.
  • Dispersing agents such as sodium isopropyl naphthalene sulfonate, dioctyl sodium sulfosuccinate, N-octadecyl disodium sulfosuccinaminate, ammonium caseinate, gelatin, glue, gum arabic, etc. may be added to either component if desired.
  • the preparation of these dispersions is illustrated in greater detail hereinafter.
  • 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 excess 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 alkylated methylol melamine-higher aliphatic amido finishing composition which may be applied to fabrics may vary considerably depending upon the nature of the fabric treated and the particular flnish desired. Fabrics of wool, silk, rayon, 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.
  • 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, acetic acid, mineral acids such as sulfurous acid and others may also be used.
  • Other catalysts for the curing of alkylated methylol melamine resins are known to chemists in the resin art and may be employed.
  • the curing temperatures are in general quite low and 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 processor. 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 ouring the resin at moderate temperatures within the range of about 240280 F.
  • thefabric after being impregnated with the desired amount of my finishing composition may be framed to width on a pin tenter, dried, batched up on a shell and persion of the alkylated methylol melamine, both I allowed to stand hot to obtain a total drying and heating time sufficient to dry the cloth and insolubilize the resin in the fabric.
  • 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 given a short mild soaping which renders it soft and pliable.
  • the fabric may then be given other usual finishing treatments such as decatizing, brushing, shearing, pressing, etc.
  • My process may be employed with both colored and uncolo'red goods without appreciably afiecting the color or shade and without damage to the material.
  • the mixture at a pH of 6.4 was then heated to distill a mixture of methanol and water, anhydrous methanol beingcontinuously added to replace the distillate. After ⁇ , heating in this way for about 6 to 7 hours, one part of the distillate would tolerate 100 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%, v
  • Samples of 80 x 80 cotton percale were impregnated with this dispersion by the dip and nip processes, regulating the take up so that the fabric contains approximately 11.5 percent by weight of the methylated methylol melamine-methylol stearamide constituents.
  • the impregnated fabric was then dried and cured for 7 minutes at 290 F.
  • the treated cloth samples were then given a short soaping for one-half hour at 160 F. in V percent soap solution, rinsed and dried.
  • a weighed 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 drained for 10 seconds, rolled between pieces of absorbent paper to remove surface water, and then weighed. The increase in weight was expressed as percent water absorbed, based on the original dryweight of the cloth. An untreated sample of the cloth absorbed from 90- 100% of its weight of water. The results of these spray tests are in the following table.
  • Dispersible textile treating compositions suitable for use in my process may also be prepared by methods involving the use of less solvent and fewer manipulative steps.
  • 50 parts by weight of crude stearamide, 90 parts by weight of 95% ethyl alcohol and 1'7 parts by weight of a 10% solution of sodium dioctyl sulfosuocinate were placed in a reaction vessel fitted with stirrer, reflux condenser and thermometer. This mixture was heated to reflux to dissolve all of the stearamide and then it was cooled to 70 C. 6.2 parts by weight of 30% sodium hydroxide dissolved in 23.2 parts by weight of 37% formaldehyde was then added to the reaction mixture and the contents of the vessel kept at ID-75 C. for one hour.
  • a similar product was prepared as follows: 50 parts by weight of crude stearamide and 90 parts by weight of denatured alcohol were placed in a reaction vessel and heated to about 80 C. to obtain a clear solution. After cooling the solution 414 parts by weight of 80% methylated .methylol melamine in methanol was added. 20 parts by weight of a 37% formaldehyde solution and 5.2 parts by weight of 37% sodium hydroxide were immediately added to the reaction mixture. The temperature was then slowly raised to 75 C. at which point a clear solution was obtained. Heating was continued at '10-'75 C. for 1% hours. At the end of this time the temperature was raised to 78 C. to clear up the solution and it was then poured into a vessel and cooled slowly.
  • Aqueous dispersions suitable for the impregnation of fabrics were prepared by mixing 72 parts of the above described paste with 72 parts by weight of water and 20 parts by weight of a 10% solution of sodium isopropyl naphthalene sulfonate. The mixture was heated to boiling and the clear solution then further diluted with 226 parts by weight of water while rapidly stirring. To this dispersion was added 20 parts by weight of a 10% solution of diammonium hydrogen phosphate. Pieces of 80 x 80 cotton percale were then impregnated with the mixture and after curing and securing the test pieces were found to have a water-repellency of the order shown by the results in the above table.
  • lauroylcyanamide, stearoylurea, methylol lauramide were also dispersed with methylatedmethylol melamine, applied to cotton fabric and the fabric dried and heat cured as described above.
  • These fabrics after soaping at 160 F. in /2 percent soap solution for 30 minutes showed water repellency of the order of compounds set forth in the above table. The water repellency of the fabrics was also found to be maintained despite soaping for periods of 4 hours and dry cleaning and soaping for 30 minutes.
  • a textile finishing composition comprising a dispersion of an alkylated methylol melamine having alkyl groups of not more than four carbon atoms and a compound having an alkyl radical of at least seven carbon atoms and containing a nitrogen atom having attached thereto a carbonyl radical and a reactive substituent selected from the group consisting of H and alkylol radicals.
  • A'textile finishing composition comprising an aqueous dispersion of methylated methylol melamin and methylol stearamide, said methylol stearamide being present in the dispersion in amounts corresponding to about 0.5 parts by weight to 5.0 parts by weight for each ten parts by weight of methylated methylol melamine.
  • a textile finishing composition comprising an aqueous dispersion of methylated methylol melamine and methylol lauramide, said methylol lauramide being present in the dispersion in amounts corresponding to about 0.5 parts to 5.0 parts by weight for each. ten parts by weight of methylated methylol melamine.
  • a method of finishing a. textile fabric which comprises treating the textile fabric with a dispersion of an alkylated methylol melamine having an alkyl group of not more than four carbon atoms and a compound having an alkyl radical of at least seven carbon atoms and containing a nitrogen atom having attached thereto a carbonyl radical and a reactive substituent selected from the group consisting of H and alkylol radicals, and thereafter heating the treated textile fabric to insolubilize the resin-forming eonstituents therein.
  • a method of finishing textile fabrics which comprises impregnating the textile fabrics with an aqueous dispersion of a methylated methylol melamine and methylol stearamide, said methylol stearamide being present in the dispersion in amounts corresponding to about 0.5 to 5.0 parts by weight for each ten parts by weight of methylated methylol melamine and thereafter heating the textile fabric within the range of 200 to 300 F. to cure the resin-forming constituents to a water-insoluble state.
  • a textile fabric of improved water repellency containing a substantially -water-insoluble resinous composition comprising a heat cured mixture of an, alkylated methylol melamine having alkyl groups of not more than four carbon atoms and a compound having an alkyl radical of at least seven carbon atoms and containing a nitrogen atom having attached thereto a carbonyl radical and a reactive substituent selected from the group consistingof H and alkylol radicals.
  • a textile fabric of improved water repellency containing a substantially water insoluble resinous composition comprising a heat cured mixture of a methylated methylol melamine and stearamide.
  • a textile finishing composition comprising a dispersion of an alkylated methylol melamine jbon atoms and a compound having an alkyl radical of at least seven carbon atoms and containing a nitrogen atom having attached thereto a carbonyl radical and a reactive alkylol radical.
  • a textile finishing composition comprising an aqueous dispersion of a methylated methylol melamine and an amide of an aliphatic monocarboxylic acid of at least eight carbon atoms, said amide having a reactive hydrogen attached to the nitrogen atom thereof.
  • a textile finishing composition comprising an aqueous dispersion of a methylated methylol melamine and an amide of an aliphatic monocarboxylic acid of at least eight carbon atoms, said amide having a reactive alkylol radical attached to the nitrogen atom thereof.
  • a textile finishing composition comprising an aqueous dispersion of an alkylated methylol melamine having alkyl groups of not more than four carbon atoms and up to a substantially equimolecular proportion of an amide of an aliphatic mono-carboxylic acid of at least eight carbon atoms, said amide having a reaction hydrogen attached to the nitrogen atom thereof.
  • a textile finishing composition comprising an aqueous dispersion of methylated methylol melamine and up to a substantially equi-molecular proportion of stearamide.
  • a method of finishing textile fabrics which comprises impregnating the textile fabric with an aqueous dispersion of a methylated methylol melamine and an amide of an aliphatic monocarboxylic acid of at least eight carbon atoms, said amide having a reactive hydrogen attached to the nitrogen atom thereof and being present in the dispersion in amounts up to about an equi-molecular proportion based on the content of methylated methylol melamine therein and thereafter heating the textile fabric to cure the resin-forming constituents to a water insoluble state.
  • a textile fabric of improved water repellency containing a substantially water insoluble resinous composition comprising a heat cured mixture of a methylated methylol melamine and a compound having an alkyl radical of at least seven carbon atoms and containing a nitrogen atom having attached thereto a carbonyl radical and a reactive hydrogen substituent.
  • a textile fabric of improved water repellency containing a substantially water insoluble resinous composition comprising a heat cured mixture of a methylated methylol melamine and a compound having an alkyl radical of at least seven carbon atoms and containing a nitrogen atom having attached thereto a carbonyl radical and a reactive alkylol radical.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US434349A 1942-03-12 1942-03-12 Textile finishing Expired - Lifetime US2357273A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
BE475511D BE475511A (en, 2012) 1942-03-12
NL69462D NL69462C (en, 2012) 1942-03-12
LU28759D LU28759A1 (en, 2012) 1942-03-12
US434349A US2357273A (en) 1942-03-12 1942-03-12 Textile finishing
GB1701/43A GB607950A (en) 1942-03-12 1943-02-02 Improvements in or relating to finishing textile fabrics and compositions therefor
CH263255D CH263255A (de) 1942-03-12 1945-06-11 Beständiges Präparat zum Behandeln von Textilien.
ES0179109A ES179109A1 (es) 1942-03-12 1947-07-28 Una mejora en la técnica del acabado de los textiles
FR950928D FR950928A (fr) 1942-03-12 1947-08-04 Procédé pour le traitement et le finissage de matières textiles
DEA3493A DE864986C (de) 1942-03-12 1950-09-13 Praeparat und Verfahren zum Appretieren von Textilien

Applications Claiming Priority (1)

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US434349A US2357273A (en) 1942-03-12 1942-03-12 Textile finishing

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Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2416884A (en) * 1942-09-09 1947-03-04 Du Pont Methylated methylolmelamine as a fixing agent for dyed cotton textiles
US2446864A (en) * 1944-06-26 1948-08-10 Quaker Chemical Products Corp Composition and process for imparting durable water repellent finish to textiles
US2491249A (en) * 1945-04-30 1949-12-13 American Cyanamid Co Water repellent composition containing stearamide and methylated methylol melamine
US2505649A (en) * 1947-07-30 1950-04-25 Du Pont Process for preparing water-repellent compositions
US2509174A (en) * 1947-05-22 1950-05-23 Monsanto Chemicals Process of waterproofing textile fabrics
US2510522A (en) * 1944-12-09 1950-06-06 Montclair Res Corp Textile treating products and process of making
US2537667A (en) * 1944-08-24 1951-01-09 Monsanto Chemicals Waterproofing of fibrous products
US2550746A (en) * 1947-06-02 1951-05-01 American Cyanamid Co Thermosetting compositions comprising an aminoplast and alkyl amidines incorporated therein
US2676936A (en) * 1952-01-09 1954-04-27 Du Pont Aqueous textile finishing composition containing methylol higher fatty acid monoamides
DE921300C (de) * 1948-10-10 1954-12-13 Cassella Farbwerke Mainkur Ag Verfahren zur Veredelung von Fasermaterial
US2704750A (en) * 1951-07-03 1955-03-22 Sherwin Williams Co Aminoplast resins
US2783231A (en) * 1951-08-31 1957-02-26 Ciba Ltd Salts of new hardenable, basic, ternary condensation products
US2819179A (en) * 1954-01-18 1958-01-07 American Cyanamid Co Textile finishing process
US2861054A (en) * 1953-06-03 1958-11-18 Montclair Res Corp Water repellents techniques
US2959519A (en) * 1958-08-11 1960-11-08 Monsanto Chemicals Fungicidal composition comprising a 2-halo-4, 6-bis (amino)-s-triazine
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
US2981704A (en) * 1956-04-12 1961-04-25 American Cyanamid Co Water repellent, method of impregnating textiles with same, and textiles bearing same
US3054699A (en) * 1957-06-12 1962-09-18 Ici Ltd Water-soluble latent curing catalysts for textile treatment resins
US3074814A (en) * 1958-01-15 1963-01-22 Ici Ltd Treatment of cellulosic materials
US3161518A (en) * 1957-11-01 1964-12-15 Lithoplate Inc Diazo sensitized lithographic plate comprising a hydrophilic amine formaldehyde intermediate layer
DE1234670B (de) * 1957-05-21 1967-02-23 Nisshin Cotton Spinning Compan Verfahren zum Knitterfestmaschen von Baumwoll- und Baumwollmischgeweben
US3306865A (en) * 1962-09-06 1967-02-28 Gen Mills Inc Compositions prepared from certain substituted melamines and polyamides derived from polymeric fat acids
US3508958A (en) * 1966-06-16 1970-04-28 Ciba Ltd Process for producing a water - repellent finish fast to washing on fibrous materials

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1078080B (de) * 1952-12-15 1960-03-24 Chem Fab Dueren G M B H Verfahren zur Veredlung, insbesondere zur krumpffreien Ausruestung von cellulosehaltigen Textilien
DE1090627B (de) * 1957-05-22 1960-10-13 Basf Ag Verfahren zum Hydrophobieren hydroxylgruppenhaltiger hochmolekularer Stoffe
EG22306A (en) 1999-11-15 2002-12-31 Shell Int Research Expanding a tubular element in a wellbore

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2416884A (en) * 1942-09-09 1947-03-04 Du Pont Methylated methylolmelamine as a fixing agent for dyed cotton textiles
US2446864A (en) * 1944-06-26 1948-08-10 Quaker Chemical Products Corp Composition and process for imparting durable water repellent finish to textiles
US2537667A (en) * 1944-08-24 1951-01-09 Monsanto Chemicals Waterproofing of fibrous products
US2510522A (en) * 1944-12-09 1950-06-06 Montclair Res Corp Textile treating products and process of making
US2491249A (en) * 1945-04-30 1949-12-13 American Cyanamid Co Water repellent composition containing stearamide and methylated methylol melamine
US2509174A (en) * 1947-05-22 1950-05-23 Monsanto Chemicals Process of waterproofing textile fabrics
US2550746A (en) * 1947-06-02 1951-05-01 American Cyanamid Co Thermosetting compositions comprising an aminoplast and alkyl amidines incorporated therein
US2505649A (en) * 1947-07-30 1950-04-25 Du Pont Process for preparing water-repellent compositions
DE921300C (de) * 1948-10-10 1954-12-13 Cassella Farbwerke Mainkur Ag Verfahren zur Veredelung von Fasermaterial
US2704750A (en) * 1951-07-03 1955-03-22 Sherwin Williams Co Aminoplast resins
US2783231A (en) * 1951-08-31 1957-02-26 Ciba Ltd Salts of new hardenable, basic, ternary condensation products
US2676936A (en) * 1952-01-09 1954-04-27 Du Pont Aqueous textile finishing composition containing methylol higher fatty acid monoamides
US2861054A (en) * 1953-06-03 1958-11-18 Montclair Res Corp Water repellents techniques
US2819179A (en) * 1954-01-18 1958-01-07 American Cyanamid Co Textile finishing process
US2981704A (en) * 1956-04-12 1961-04-25 American Cyanamid Co Water repellent, method of impregnating textiles with same, and textiles bearing same
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
DE1234670B (de) * 1957-05-21 1967-02-23 Nisshin Cotton Spinning Compan Verfahren zum Knitterfestmaschen von Baumwoll- und Baumwollmischgeweben
US3054699A (en) * 1957-06-12 1962-09-18 Ici Ltd Water-soluble latent curing catalysts for textile treatment resins
US3161518A (en) * 1957-11-01 1964-12-15 Lithoplate Inc Diazo sensitized lithographic plate comprising a hydrophilic amine formaldehyde intermediate layer
US3074814A (en) * 1958-01-15 1963-01-22 Ici Ltd Treatment of cellulosic materials
US2959519A (en) * 1958-08-11 1960-11-08 Monsanto Chemicals Fungicidal composition comprising a 2-halo-4, 6-bis (amino)-s-triazine
US3306865A (en) * 1962-09-06 1967-02-28 Gen Mills Inc Compositions prepared from certain substituted melamines and polyamides derived from polymeric fat acids
US3508958A (en) * 1966-06-16 1970-04-28 Ciba Ltd Process for producing a water - repellent finish fast to washing on fibrous materials

Also Published As

Publication number Publication date
LU28759A1 (en, 2012)
GB607950A (en) 1948-09-08
NL69462C (en, 2012) 1900-01-01
FR950928A (fr) 1949-10-11
CH263255A (de) 1949-08-31
ES179109A1 (es) 1947-10-01
DE864986C (de) 1953-01-29
BE475511A (en, 2012) 1900-01-01

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