US3617195A - Textile finishing process using a chlorinated hydrocarbon as the reactant solvent - Google Patents

Textile finishing process using a chlorinated hydrocarbon as the reactant solvent Download PDF

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Publication number
US3617195A
US3617195A US3617195DA US3617195A US 3617195 A US3617195 A US 3617195A US 3617195D A US3617195D A US 3617195DA US 3617195 A US3617195 A US 3617195A
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United States
Prior art keywords
textile material
percent
acid
resin precondensate
secs
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English (en)
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James Albert Moyse
Alexander Parkinson
James William Roberts
Brian Crosbie Fielding
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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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
    • Y10T442/2369—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

  • a process for thetreatment of textile materials containing at least 20 percent by weight of cellulosic material which comprises impregnating the said textile material with a solution or dispersion in a halogenated hydrocarbon solvent of a resin precondensate as hereinafter defined which reacts under acid conditions, together with a catalyst which is an acid or an acidgenerating substance, immediately thereafter subjecting the textile material so impregnated to the action of hot water or steam and thereafter heating the textile material.
  • a resin precondensate an initial stagecondensation product of formaldehyde with a nitrogen-containing compound, which is capable of reacting with itself under acid conditions to give a fully cured resin and/or is also capable of reacting with the hydroxyl groups present in the cellulosic textile material.
  • Resin precondensates suitable for use inthe process of the invention include the initial stage condensation products of formaldehyde with urea, thiourea, dicyandiamide, amides, carbamates, aminotriazines, urons, ureins, ureides, imidazolidinones, pyrimidinones and triazinones, especially the methylol derivatives of such compounds and their lower alkyl ethers.
  • Preferred resin precondensates are the alkyl ethers of the aforesaid methylol compounds in which the alkyl groups contain from one to four carbon atoms.
  • Such preferred resin precondensates include methoxymethylurea, polymethoxymethylmelamine, 1,3- dimethoxymethyl-4,5-dihydroxy-imidazolidin-Z-one and 1,3- dimethoxymethyl-hexahydropyrimidin-Z-one.
  • Halogenated hydrocarbon solvents which may be employed in the process of the invention include any of the commercially available halogenated hydrocarbons; it is preferable that the solvent should be sufficiently volatile to be capable of being rapidly removed from thetextile material on treatment with hot water or steam.
  • Particularly suitable solvents are chlorinated and chlorofluorinated hydrocarbon solvents, for example trichloroethylene, perchloroethylene and l:l:ltrichloroethane.
  • Suitable solvent-soluble acids include, for example, monochloracetic acid, dodecylbenzene sulphonic acid and 2,2-bis(hydroxymethyl) butylphosphonic acid;
  • suitable solvent-soluble acidgenerating compounds include, for example, esters such as methyl p-toluene-sulphonate and quaternary ammonium salts such as cetyl pyridinium bromide and stearamidomethylpyridinium chloride.
  • the reactive components which are to be applied,to the cellulosic textile material according to the process of the invention are initially dissolved or dispersed in the halogenated hydrocarbon solvent, and the resulting solution or dispersion is applied to the textile material by any of the known methods, such as impregnating, coating or spraying.
  • the textile material may then be'squeezed, if desired. to remove any excess of they solution.
  • the textile material so treated is then immediately conducted either into a vessel of hot water or into a chamber containing an atmosphere of steam. in the case where hot water is employed, the water is conveniently maintained at a temperature of from 80 C. to 100 C.
  • the textile material is allowed to remain in contact with the hot water for a period of from secs. to 60 secs. It is, however, preferred to subject the textile material to which the solution has been applied to the action of a steamatmosphere.
  • the steam is preferably at atmospheric pressure, so that the textile material attains a temperature of from 80 C. to 100 C., but superheated steam under pressure may be employed if higher temperatures are desired.
  • the textile material is preferably maintained in contact with the steam atmosphere for a period of from 5 secs. to 60 secs.
  • the steam treatment may conveniently be carried out in a steam chamber such as that described in British Pat. specification No. 916,338 or that described in our copending 7 application No. 42620/66.
  • the textile material After the treatment with hot water or steam, the textile material is heated in order to bring about the necessary curing of the resin precondensate under the influence of the acid catalyst.
  • the heating operation may be carried out'within a wide range of temperatures, but it is preferred to heat the textile material at a temperature within the range 120 C. to 200 C.
  • the duration of the heating may vary between 10 seconds and minutes, but is preferably between 1 and 5 minutes; normally thehigher the temperature which is employed, the shorter is the heating time necessary.
  • the heating operation may if desired be preceded by a drying step in which the textile material is heated at a lower temperature, for example in the range 50 C. to 120 C. Alternatively, the heating operation may optionally be deferred until'after the textile material has been made up into a garment.
  • the resin-treated textile material may optionally also be subjected to a mild washing treatment to remove residual formaldehyde and/or acid.
  • Thetreatment of the textile material with hot water or steam immediately following the application of the solution of the resin precondensate and the acid catalyst is an essential part of the process of the invention. Not only does this treatment serve to remove the halogenated hydrocarbon solvent by violatilisation, but it also brings about an unexpected enhancement of the desirable properties of the textile material which are conferred by.the process. if the halogenated hydrocarbon solventis removed from the textile material by the application of dry heat, the-beneficial effects of the treatment are very muchdiminished.
  • T he concentration of the resin precondensate in the solution which is applied to the textile material may be varied within wide limits, but in general a concentration of from 3 percent to 20 percent by weight of the solution ispreferred.
  • the amount of the acid catalyst present in the solution is normally from 5 percent to 20 percent of the weight of the resin precondensate.
  • the amount of the resin precondensate which is applied to the textile material by the process of the invention may be varied accordingto the magnitude of the treatmenteffect which it is desired to achieve, but in general an amount, of from 2.5 percent to 15 percent of the dry weight of the textile material is preferred.
  • the process of the invention may with advantage be carried out in such away that the halogenated hydrocarbon solvent is recovered for reuseafter its removal from the textile material by hot water or steam.
  • a solvent recovery system such as' that described in British Pat. specificationNo.
  • the solvent When the solvent is removed by the preferred method of treating with steam, the solvent may conveniently be recovered in conventional manner, for example by condensation of the vapors by meansof a condenser positioned inside. or outside the flash-off vessel, the condensate being passed to a water separator to remove water from the liquid solvent, as described, for example, in our copending application No. 4 2620/66. lnthis way loss-of solvent va or tothe atmosphere can be obviated, and the resulting liquid solvent can be reusedin the treatment of further textile material.
  • Cellulosic textilematerials which may be treated according .to the process'of the invention include fibers, yarns and fabrics containing at least 20 percent by weight of cellulosic material,
  • a synthetic polymeric material such as a polyester, such blends containing at least 20 percent by weight, and desirably 50 percent by weight, of cellulosic material.
  • Treatment of such textile materials by the process of the invention results in a substantial improvement in the crease-resistance and easy-care properties of the materials.
  • Such other textile treatment agents include lubricants and softeners, for example low molecular weight polyethylene waxes, water repellent agents. for example slllcones. methylolstearamide and steurumldomethyl pyridinium chloride. and stiffening agents. for example polyvinyl acetate.
  • EXAMPLE l A mercerized cotton poplin fabric is impregnated in a solution of 6.2 parts of polymethoxymethylmelamine, prepared as described below, and 0.6 part of monochloracetic acid in 93 parts of trichloroethylene. The fabric is then passed through squeeze rollers at such a pressure that the amount of trichlorethylene solution retained by the fabric is 65 percent of its dry weight. It is attached to a frame and immersed in a steam chamber at 95 C. for 30 seconds in order to remove the solvent. The fabric is then heated at l50-l55 C. for 3 minutes.
  • the resulting fabric is found to possess good crease resistance (when measured by British Standard Method of Test 8.5. 3086:l959)-and superior smooth-drying performance to the untreated cotton. This improvement is illustrated by the following crease recovery figures:
  • Untreated Treated fabric fabric Crease recovery angle l7l 265 (warp weft) The finish is therefore durable to the above washing treatment.
  • the solvent-soluble polymethoxymethylmelamine used in the above treatment is prepared as follows:
  • EXAMPLE 2 A mercerized cotton poplin fabric is impregnated with a solution containing 6.2 parts of methoxymethylurea, prepared as described below, and 0.77 part of stearamidomethyl pyridinium chloride in 93 parts of trichloroethylene. The fabric is squeezed through a pad mangle so that the amount of solution it retains is 65 percent of its own weight. The solvent is then removed from the fabric by attaching the fabric to a frame and immersing the frame in a steam chamber at 95 C. for 30 seconds. The fabric is finally heated at C. for 3 minutes.
  • the treated cotton is found to possess a crease recovery angle warp-i-weft) of 223, while that of the untreated is .1 36.
  • the solvent-soluble methoxymethylurea used in the above treatment is prepared as follows:
  • urea 180 Parts of urea are added to 794 parts of5l percent w/w methanolic formaldehyde solution which have been basified by the addition of 10.8 parts of 47 percent w/w aqueous caustic soda solution.
  • the solution is stirred at 60-65 C. during 3 hours and cooled to room temperature.
  • the solution is acidified to pH 2 by the addition of about 10 parts of concentrated hydrochloric acid, the solution then being stirred at 25-30 C. during 2 hours.
  • the solution is basified to pH 9.5
  • a process for the treatment of textile materials containing at least 20 percent by weight of cellulosic material which comprises the steps of (a) impregnating the said textile material with a liquor comprising (i) a halogenated aliphatic hydrocarbon solvent, (ii) a resin precondensate which is an initial stage condensation product of formaldehyde with a compound containing the grouping where X is oxygen, sulphur or an imino group and which is capable of reacting with itself under acid conditions to give a fully cured resin and/or is capable of reacting with the hydroxyl group present in the said cellulosic material, and (iii) a catalyst for the said resin precondensate selected from acids and acid-generating substances, (b) immediately after the said impregnation treating the textile material with an aqueous agent selected from hot water and steam, and (c) thereafter heating the textile material at 120 to 200 C. for a period of from 10 seconds to 30 minutes.
  • the resin precondensate is an alkyl ether of a methylol derivative selected from the methylol derivatives of urea, thiourea, dicyandiamide, an amide, a carbamate, an aminotriazine, a uron, a urein, a ureide, an imidazolidimone, a pyrimidinone and a triazinone the alkyl group of the alkyl ether containing from one to four carbon atoms.
  • resin precondensate is selected from methoxymethylurea, polymethoxy-methylmelamine, l,3-dimethoxymethyl-4,5- dihydroxy-imidazolidin-Z-one and l,3-dimethoxymethyl-hexahydropyrimidin-Z-one.
  • halogenated hydrocarbon solvent is selected from trichloroethylene, perchloroethylene and 1,1 ;l-trichloroethane.
  • catalyst is an acid selected from monochloroacetic acid, dodecylbenzenesulphonic acid and 2,Z-(bishydroxmethyU-butylphosphonic acid.

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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)
  • Phenolic Resins Or Amino Resins (AREA)
US3617195D 1967-06-26 1968-06-24 Textile finishing process using a chlorinated hydrocarbon as the reactant solvent Expired - Lifetime US3617195A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2942467 1967-06-26
GB2232668 1968-05-10

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US3617195A true US3617195A (en) 1971-11-02

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US3617194D Expired - Lifetime US3617194A (en) 1967-06-26 1968-06-24 Textile finishing process using chlorinated hydrocarbon solvents and sulfohalide reaction catalysts

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US (2) US3617195A (forum.php)
BE (1) BE717196A (forum.php)
CH (2) CH950868A4 (forum.php)
DE (1) DE1769665C3 (forum.php)
FR (1) FR1582531A (forum.php)
GB (1) GB1204163A (forum.php)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3775051A (en) * 1969-07-07 1973-11-27 Ici America Inc Surfactants for solvent/water systems and textile treating compositions
US3901984A (en) * 1973-06-20 1975-08-26 Us Agriculture Solvent vapor fiberset process for durable press finishing of cellulosic fabrics
US3948600A (en) * 1975-02-27 1976-04-06 The United States Of America As Represented By The Secretary Of Agriculture Selected ammonium sulfonate catalysts for an improved process utilizing mild curing conditions in durable press finishing of cellulose-containing fabrics
US3989457A (en) * 1974-03-22 1976-11-02 Heberlein & Co. Ag Finishing processes for textile materials
US4080480A (en) * 1976-06-09 1978-03-21 The United States Of America As Represented By The Secretary Of Agriculture Catalyzing cellulosic textile finishing processes with phosphonic acid derivatives
US4092106A (en) * 1975-05-16 1978-05-30 The United States Of America As Represented By The Secretary Of Agriculture Emulsion systems for imparting durable press properties to cotton and cotton-polyester blended textiles
US4139661A (en) * 1977-03-09 1979-02-13 Anagnostis Demetrius B Dewrinkling and permanent crease reforming of garments
US20110006257A1 (en) * 2002-02-05 2011-01-13 Biesecker James L Stabilized powdered formaldehyde

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007018922A2 (en) * 2005-07-22 2007-02-15 Arkema Inc. Organosulfonyl latent acids for petroleum well acidizing

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1174859A (fr) * 1956-05-09 1959-03-17 Basf Ag Procédé pour l'ennobilissement de fibres, de fils et de tissus
US3183282A (en) * 1956-07-27 1965-05-11 Rohm & Haas Non-aqueous solutions of acrylic ester/acid copolymer and thermosetting alkylated aminoplast resin-forming condensate
US3473175A (en) * 1960-12-23 1969-10-21 American Permac Inc Process and apparatus for the controlled treatment of textiles

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1174859A (fr) * 1956-05-09 1959-03-17 Basf Ag Procédé pour l'ennobilissement de fibres, de fils et de tissus
US3183282A (en) * 1956-07-27 1965-05-11 Rohm & Haas Non-aqueous solutions of acrylic ester/acid copolymer and thermosetting alkylated aminoplast resin-forming condensate
US3473175A (en) * 1960-12-23 1969-10-21 American Permac Inc Process and apparatus for the controlled treatment of textiles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Hofstetter, Melliand Textilberichto, March, 1969, pp. 321 334 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3775051A (en) * 1969-07-07 1973-11-27 Ici America Inc Surfactants for solvent/water systems and textile treating compositions
US3901984A (en) * 1973-06-20 1975-08-26 Us Agriculture Solvent vapor fiberset process for durable press finishing of cellulosic fabrics
US3989457A (en) * 1974-03-22 1976-11-02 Heberlein & Co. Ag Finishing processes for textile materials
US3948600A (en) * 1975-02-27 1976-04-06 The United States Of America As Represented By The Secretary Of Agriculture Selected ammonium sulfonate catalysts for an improved process utilizing mild curing conditions in durable press finishing of cellulose-containing fabrics
US4092106A (en) * 1975-05-16 1978-05-30 The United States Of America As Represented By The Secretary Of Agriculture Emulsion systems for imparting durable press properties to cotton and cotton-polyester blended textiles
US4080480A (en) * 1976-06-09 1978-03-21 The United States Of America As Represented By The Secretary Of Agriculture Catalyzing cellulosic textile finishing processes with phosphonic acid derivatives
US4139661A (en) * 1977-03-09 1979-02-13 Anagnostis Demetrius B Dewrinkling and permanent crease reforming of garments
US20110006257A1 (en) * 2002-02-05 2011-01-13 Biesecker James L Stabilized powdered formaldehyde

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Publication number Publication date
BE717196A (forum.php) 1968-12-27
CH950868A4 (forum.php) 1971-04-15
DE1769665C3 (de) 1974-10-24
FR1582531A (forum.php) 1969-10-03
US3617194A (en) 1971-11-02
DE1769665A1 (de) 1970-11-12
GB1204163A (en) 1970-09-03
CH512627A (de) 1971-04-15

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