US2859136A - Process for the treatment of fabrics with resinous condensation products - Google Patents

Process for the treatment of fabrics with resinous condensation products Download PDF

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Publication number
US2859136A
US2859136A US529774A US52977455A US2859136A US 2859136 A US2859136 A US 2859136A US 529774 A US529774 A US 529774A US 52977455 A US52977455 A US 52977455A US 2859136 A US2859136 A US 2859136A
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Prior art keywords
resin
formaldehyde
fabric
steam
urea
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Expired - Lifetime
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US529774A
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English (en)
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Marsh John Thompson
Blease Ronald Arthur
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Tootal Broadhurst Lee Co Ltd
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Tootal Broadhurst Lee Co Ltd
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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
    • 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
    • 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

Definitions

  • ther object of the invention to give increased abrasion resistance to textile fabrics composed wholly or mainly of regenerated cellulose, and having insolubilised by hea ing in the fibres thereof, a melamine-formaldehyde resin ormixed melamine-formaldehyde urea-formaldehyde.
  • thermohardening synthetic resin in the fibres of a textile fabric is to impregnate the fabric with an aqueous solution 'con-. taining theresin-forming ingredients or an intermediate condensation product thereof and an acidic catalyst and thereafter'to drythe impregnated fabric and heat it to Even.
  • the atmosphere in which the final heating to insolublise the resin is eifected shall contain at least 50%-;
  • partial pressure of steam expressed as a percentage-off the total pressure of air and steam, measured at substantially the temperature of .the heating chamber.
  • Fig. 1 is a graphic representation of the comparison of the" results of theprocess with oven dry curing and i Fig. 2 is a vertical cross-sectional view of the testing apparatus ,used.
  • the following method may be employed; A sample of the atmosphere of the heating chamber (oven) is withdrawn, the steam condensed therefrom and the proportion of residual measured.
  • Theflask 1 the volume of which is small compared with. the oven, and which is surrounded by a removable heating jacket 2, is connected by a tube 3 having a valve 4 to the oven (not shown), by a tube 5 having a valve 6 to a vacuum pump (not shown) and by a tube 7 to a mercury manometer or to a Bourdon gauge (not shown).
  • the flask 1 is provided with a thermometer 8.
  • the flask 1 is exhaustedby the vacuum pump, the valve 6 being open and the valve 4 closed and then brought to the same temperature as the oven.
  • valve 6 is shut and the valve 4 opened for a few seconds to allow a sample of the. oven atmosphere to pass into the flask 1.
  • the valve 4 is closed thus leaving the flask connected only to the manometer or the Boudon gauge.
  • the heating jacket 2 is then removed and the flask 1 cooled'down to room temperature.
  • the .water vapour condenses on the sides of the flask 1 and the cooling of the residual air also leads toa reduction in pressure.
  • the final pressure in the flask 1 is read on on the manometer or the Bourdon gauge, and a knowledge of this and of the initial and final temperatures enables one to calculate the steam content as in the following calculation.
  • Atmospheric'pressure 760 mm.
  • Table I shows the result of a series'of tests in which diflferent portions of the same fabric composed wholly of viscose spun rayon were immanometer 500 t wear was measured on the ringwear testing machine described in the Journal of the Textile Institute,-l935, 26, 93P.
  • the improvement is particularly strik-n. ing when the atmosphere contains at least 50% of steam.
  • the objects of the present invention are secured by a process which comprises impregnating the textile fabric with an aqueous solution of water-soluble amino-formaldehyde resin-forming ingredients containing) an acidic catalyst for the resin-formation, drying the fabric and heating it to produce water-insoluble thermoy resin from, said resin-forming containing at least 50% hardened synthetic ingredients in an atmosphere of superheated steam.
  • thermohardening syntheticresins employed in our.
  • urea-formaldehyde resin melamine-formaldehyde resin pregnated with the same aqueous solution Qfurea-formand mixed melamine-formaldehyde urea formaldehyde.
  • melamine includes substituted rnelamincs, such as alkylated melamine.
  • the textile materialtreated in accordance with the present invention does not consist wholly of regenw erated cellulose, it preferably contains more than about by weight of regenerated cellulose.
  • the regenerated cellulose is, preferably, viscose rayon.
  • tion is of particular value when the regenerated cellulose is spun viscose rayon.
  • urea-formaldehyde resin within and not between the fibres of a regenerated cellu-, lose fabric without undue loss of resistance to abrasion, of a suflicient proportion of urea-formaldehyde resin, melamine-formaldehyde resin or mixed melamineformaldehyde urea-formaldehyde resin will give creaseresistance, and even a degree of recovery from creasing1 comparable with that of high grade wool fabrics.
  • urea-formaldehyde resin an amount of, for
  • the temperature and time of heating to insolubilise the resin when employing an atmosphere, containing'at least 50% of superheated steam according to'the present invention,may be the same as that which'wouldbe employed without added steam or with'the smallproportions of steam which have hitherto been customary. This, as is known, exceeds C. and preferably "exceeds C. Thus, temperatures between .”and 180 C. are suitable, for example "C.
  • Therondensation may be carried out in theipresence of. the'customary catalysts and in particular we may use apotentially acid catalyst, e. g. an ammoniumsalt or an'amine salt.
  • the acidic catalyst maybe an acid, a mixture of acids, a mixture of'an acid and a salt, or, preferably, a potentially acid substance i. e. one which is capable of becoming acid (or more acid, e. g. a mixture of calcium chloride and boric acid) or of liberating acid during the treatment, for example aluminum chloride .or, most 'suitably, an'ammonium salt or an amine salt such as ammonium thiocyanate or ammonium dihydrogen phosand a urea-formaldehyde intermediate condensationproduct are prepared, mixed and suitablycatalysed; oralternatively melamineand urea are mixed and then partially condensed with formaldehyde before catalysing.
  • a potentially acid substance i. e. one which is capable of becoming acid (or more acid, e. g. a mixture of calcium chloride and boric acid) or of liberating acid during the treatment, for example aluminum chloride .or, most 'suitably,
  • the present invention-'m-ay be "carried out with mixtures of any melamine-formaldehyde and urea-formaldehy'cle intermediate condensation products capable of being insolubilised withinthe fibres by heating; for example methylol melamine and methylol urea, alkylated methylol melamine andmethylol urea, methylol -melam;ine and alkylated methylol urea, or alkylated methylol melamine and alkylatedmethylol urea maybe used.
  • Example '1.'100 gms. urea 'and'200 cc. of neutral 40% formaldehyde were mixed together and 9 cc. ammonium hydroxide (specific gravity 0.88) added.- This mixture was then refluxed for 3 minutes and cooled to room temperature.
  • Example 2 The.following Table H shows the effect of treating two fabrics according to'the method described in Example 1 but using substantially 100% of superheated steam (steam) a compared with fabrics similarly treated but in which the resin was insolubilised without added steami(dry), Fabric 1 was a viscose rayon fabric made from 75 denier filament warp and 30s Fabric 2 was a 100% viscose spun rayon fabric made from yarn spun to 30s cotton count.
  • Table II Percent Ringwear Resin Content Fabric Steam Untreated Dry Steam Dry Steam Example 3.
  • Table III show that the improved wear resistance effect obtained by treating two fabrics according to the method described in Example 1 but using about 90% of superheated steam is substantially unaffected by washing.
  • Both parts were then washedin open width in soda ash at 90 C. for 10 seconds, then in water at 90 C. for 10 seconds, then in water at20 C. for 10 seconds, and then passed through a bath containing 1% of a sulphated fatty alcohol as a softener and dried on a stenter to 36 inches wide.
  • Fabric 4 was a dress fabric made of a blend of 16% by weight of wool and 84% by weight of viscose spun rayon.
  • Example 6 percent Dry Steam FABRIC MADE FROM A BLEND OF 16% BY WEIGHT OF Example 6.--100% viscose spun rayon and viscose spun rayon and wool mixture-fabrics were treated as in Example 5 but with repeated impregnation with diluted reaction mixtures containing 50%, 60%, and 70% of the concentrated reaction mixture so as to obtain fabrics having higher resin contents than in Example 5...
  • the resin content (based on the weight of dry fabric not containing resin), resistance to abrasion and dry recovery are shown in the following tables VII and VIII.
  • Example 8 Samples of a 100% viscosespun rayon fabric were treated as in Example 7 but each sample-was impregnated so as to retain 80% instead of 100% of its weight of the liquid. In different samples the resin was insolubilised in atmospheres containing different proportions of superheated steam.
  • Table XI shows that in fabrics containing more than 8% of melamine formaldehyde resin the resistance to abrasion, as measured by the ringwear testing machine, is improved by insolubilising the resinin atmospheres containing increasing proportions of superheated steam, and 'that' recovery from creasing is unaltered.
  • Each sample offabric was impregnated with one of the above diluted and catalysedireaction mixtures so as to retain about 80% or its weight of the liquid, partially dried on steam heatedicylinders andvthen passed on ma stenter where it was'dried to the standard-width.
  • Some samples were heated at atmospheric pressure for "2% minutes at 160 C. in an atmosphere not containing added steam (hereinafter indicated in the tables by D after the formaldehyde ratio) and some samples were heated at atmospheric pressure for.2% minutes at 160 C. in an atmosphere containing 8590% of superheated steam (hereinafter indicated in the tables by S after the formaldehyde ratio). All samples were then washedin open width first in 2% sodium carbonate at 90 C. for 10 secs., then in water at 90 C. for 10 secs. and then in water at 20 C. for 10 secs.
  • the samples to be laundered were first measured and weighed. 40-litres of water-at 40C. and 75 .gms. of soap were put into a -washin'g machine using this quantity 'of water; the samples were then washed in the washing machine with agitation for 20- minutes. After centrifugingthe samples-were separated, rinsed in 40litres of waterat 40 C. for 5 minutes, and recentrifuged. The samples were then shaken gently and pressed with a *hot; iron i.-'e. the iron'isi placed on'the cloth for a few seconds :withouti there being any horizontal movement .of
  • Table XIV shows theeifect on the laundry shrinkage
  • Table XII shows the efiect on the recovery from creasing abrasion resistance (as shown by the ringwear test resulting from repeated washings when the "fabric" is ing machine) and laundry shrinkage, of treating fabric treated according to the method described above, and with resin according to the method described above and using a reaction mixture having at least 2 molecular prousing a reaction mixture having at least 2 molecular proportions of formaldehydeto l of urea and insolubilising portions of formaldehyde to 1 of urea and insolubilising the resin in an atmosphere containing superheated steam.
  • a process of'giving increased abrasion resistancet'o a textile fabric containing at least 50% of regenerated cellulose by insolubilising in the fibers thereof, by heating,- a resinselected from the group consisting of urea-formaldehyde wherein the molecular ratio of formaldehyde to urea is from.
  • melamine-formaldehyde wherein the molecular ratio of formaldehyde to melamine-is greater than 3:1 and up to 6:1, and a mixture ofsaid urea-formaldehyde melamine-formaldehyde resins, which process comprises the steps of impregnating said fabric with an aqueous solution containing water-soluble ingredients for forming said resin, said solution also containing an acid catalyst for the resin formation-drying the fabric and heating it to produce said water-insoluble resin from said resin-forming ingredients in an atmos- 13 phere wherein at least 50% of said atmosphere is superheated steam.
  • mine-formaldehyde resins which process comprises the steps of impregnating said fabric with an aqueous solution containing water-soluble ingredients for forming said resin, said solution also containing an acid catalyst for the resin formation, drying the fabric and heating it to produce said water-insoluble resin from said resinforming ingredients in an atmosphere consisting substantially wholly of superheated steam.

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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)
US529774A 1950-07-08 1955-08-22 Process for the treatment of fabrics with resinous condensation products Expired - Lifetime US2859136A (en)

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GB17139/50A GB704143A (en) 1950-07-08 1950-07-08 Process for the treatment of fabrics with resinous condensation products

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BE (1) BE504549A (en。)
FR (1) FR1131845A (en。)
GB (1) GB704143A (en。)
NL (1) NL77270C (en。)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2988416A (en) * 1956-04-19 1961-06-13 Tootal Broadhurst Lee Co Ltd Process of creaseproofing linen fabric by applying resin, mercerizing and reapplyingresin and product produced thereby
US3050419A (en) * 1956-05-08 1962-08-21 Ciba Ltd Process for fixing aminoplasts in the wet state on cellulosic fibrous materials
US3136654A (en) * 1958-11-18 1964-06-09 Fmc Corp Manufacture of coated material
US3243252A (en) * 1961-05-18 1966-03-29 Bancroft & Sons Co J Process of methylenating cellulose textiles employing a catalyst mixture of acid, acid salt and reducing agent
US3374107A (en) * 1963-08-14 1968-03-19 West Point Pepperell Inc Process for the treatment of textiles with aminoplasts
US3472606A (en) * 1965-11-15 1969-10-14 Cotton Producers Inst Two-component wet fixation process for imparting durable press to cellulosecontaining materials
US3768969A (en) * 1971-12-21 1973-10-30 Us Agriculture Sensitized textiles with decreased formaldehyde odor
US3950589A (en) * 1972-03-23 1976-04-13 Toray Industries, Inc. Melt-resistant synthetic fiber and process for preparation thereof
US4355081A (en) * 1980-05-30 1982-10-19 James River Corporation Curing of resin impregnated cellulosics with continuously superheated steam

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1172642B (de) * 1957-12-13 1964-06-25 Ciba Geigy Verfahren zum Schuetzen von cellulosehaltigem Fasergut gegen Wettereinfluesse, insbesondere gegen Sonnenbelichtung

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2088227A (en) * 1934-09-19 1937-07-27 Tootal Broadhurst Lee Co Ltd Impregnation of textile fabrics
US2093651A (en) * 1933-02-09 1937-09-21 Gustave A Widmer Dyeing fibrous materials
US2190672A (en) * 1936-03-14 1940-02-20 Bakelite Corp Water-soluble phenol-aldehyde resins
US2299786A (en) * 1936-12-09 1942-10-27 Tootal Broadhurst Lee Co Ltd Process of treating textile materials
US2484598A (en) * 1945-06-05 1949-10-11 Alrose Chemical Company Reducing the crease and wrinkling tendencies of cellulosic textile fabrics
US2512195A (en) * 1939-03-04 1950-06-20 Bener Christian Method of waterproofing cellulose textiles
US2590850A (en) * 1949-10-10 1952-04-01 Dungler Julien Method of treating sheet material coated with gelatine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2093651A (en) * 1933-02-09 1937-09-21 Gustave A Widmer Dyeing fibrous materials
US2088227A (en) * 1934-09-19 1937-07-27 Tootal Broadhurst Lee Co Ltd Impregnation of textile fabrics
US2190672A (en) * 1936-03-14 1940-02-20 Bakelite Corp Water-soluble phenol-aldehyde resins
US2299786A (en) * 1936-12-09 1942-10-27 Tootal Broadhurst Lee Co Ltd Process of treating textile materials
US2512195A (en) * 1939-03-04 1950-06-20 Bener Christian Method of waterproofing cellulose textiles
US2484598A (en) * 1945-06-05 1949-10-11 Alrose Chemical Company Reducing the crease and wrinkling tendencies of cellulosic textile fabrics
US2590850A (en) * 1949-10-10 1952-04-01 Dungler Julien Method of treating sheet material coated with gelatine

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2988416A (en) * 1956-04-19 1961-06-13 Tootal Broadhurst Lee Co Ltd Process of creaseproofing linen fabric by applying resin, mercerizing and reapplyingresin and product produced thereby
US3050419A (en) * 1956-05-08 1962-08-21 Ciba Ltd Process for fixing aminoplasts in the wet state on cellulosic fibrous materials
US3136654A (en) * 1958-11-18 1964-06-09 Fmc Corp Manufacture of coated material
US3243252A (en) * 1961-05-18 1966-03-29 Bancroft & Sons Co J Process of methylenating cellulose textiles employing a catalyst mixture of acid, acid salt and reducing agent
US3374107A (en) * 1963-08-14 1968-03-19 West Point Pepperell Inc Process for the treatment of textiles with aminoplasts
US3472606A (en) * 1965-11-15 1969-10-14 Cotton Producers Inst Two-component wet fixation process for imparting durable press to cellulosecontaining materials
US3768969A (en) * 1971-12-21 1973-10-30 Us Agriculture Sensitized textiles with decreased formaldehyde odor
US3950589A (en) * 1972-03-23 1976-04-13 Toray Industries, Inc. Melt-resistant synthetic fiber and process for preparation thereof
US4355081A (en) * 1980-05-30 1982-10-19 James River Corporation Curing of resin impregnated cellulosics with continuously superheated steam

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BE504549A (en。)
NL77270C (en。)
FR1131845A (fr) 1957-02-28
GB704143A (en) 1954-02-17

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