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

Definitions

• CH2OH CHz-N C O CH2N CHzOH wherein R is alkyl from 1 to 8 carbon atoms and an acid catalyst.
• the thus treated textile is then thermofixed at 140 to 180 C. for one to five minutes.
• the present invention relates to 1,3-bis-hydroxymethyl-- 2-one-S-alkylcarboxylate-1,3,5-hexahydrotriazines, wherein the alkyl group contains 1 to 8 carbon atoms, and to the use thereof in finishing baths for cellulosic textile materials. It also relates to the finishing baths and to the textile materials finished with the said compounds contained in the said baths.
• Natural or artificial textile materials such as cotton and rayon, have a tendency toward becoming irreversibly creased or crumpled, because of the low spn'nginess of the constituent fibers thereof. This is why the washing of such textile materials has to be followed by an ironing operation to smooth out creases and folds formed during the laundering operation.
• Some resins notably the alkyl dimethylol-car-bamate resins, prove to be relatively difiicult to condense and develop maximum effect only at the cost of dynamometric strength losses which are prohibitive in most cases. Moreover, the permanence of the finish is rather limited timewise.
• Textile materials treated with most of the aforesaid agents suffer substantial deterioration after being bleached with hypochlorite-based or hypochlorite-generating products.
• the treated fabric is rough to the touch and require additional treatments with auxiliary softening agents.
• the present invention is concerned with finishing materials which make possible the total elimination of the aforesaid drawbacks.
• finishing materials When applied to cellulosic textile materials, they will impart thereto outstanding selfsmoothing properties in the wet, moist or dry state, as well as definitive stabilization of dimensions and particularly soft feel, these characteristics being specific to the treatment with the said finishing agents of this invention.
• the so-treated materials can be bleached with any of the conventionally employed bleaching agents, including those which are hypochlorite-based. They can be laundered without affecting the finish or the outlined desirable properties imparted thereto. Finally, due to the absence of any disagreeable odor, it is possible in most cases to forego washing aftertreatment.
• the active compounds according to the present invention are of the following formula:
• Dimethylol urea obtained from urea and formaldehyde, is condensed with one or more C to C -alkyl carbamates in equimolecular proportions relative to the starting urea, the condensation being followed by dimethylolation with formaldehyde in alkaline medium.
• Formaldehyde is reacted with one or more C to C -alkyl carbamates, and the resultant N-dimethylol alkyl carbamate is condensed with urea, after which the obtained triazone is dimethylolated with formaldehyde in alkaline medium.
• Formaldehyde is reacted with an equimolecular mixture of one or more C,- to C -alkyl carbamic acid esters and urea in aqueous solution, after which, as in the other methods, dimethylolation of the resultant triazine is carried out with formaldehyde in alkaline medium.
• hydrotriazinone derivatives of the invention have two reactive positions in the molecule, like dimethylolethyleneurea, but the absence of replaceable hydrogen atoms prevents fixation of chlorine during the bleaching of the treated cellulosic materials with hypochlorite. Moreover, the soft feel of fabrics finished with 1,3- bishydroxymethyl-2-one-S-alkylcarboxylate 1,3,5 hexahydrotria-zine (I) of this invention is ascri'bable to plasticizetion due to the ester group.
• the catalytically active inorganic salts of strong acids such as magnesium chloride hexahydrate, zinc chloride, zinc nitrate hexahydrate, magnesium nitrate, etc.
• strong acids such as magnesium chloride hexahydrate, zinc chloride, zinc nitrate hexahydrate, magnesium nitrate, etc.
• con-' centrationwhile organic acid catalysts such as formic acid, acetic acid, maleic acid, tartaric acid, lactic acid or citric acid, are used in a lower concentration of 0.1% to 0.6% by weight.
• finishing operation is carried out in per se conventional manner by foularding and then expressing to an uptake of the order of 50 to 100% by weight, drying at 60 to 110 C., and final thermofixing at 140 to 180 C. for 1 to 5 minutes, depending upon the temperature employed.
• afterwashing of the finished material is not necessary, it is recommendable in certain cases to eliminate products, such as unreacted catalyst. This is especially recommendable in the case of white textile fabrics, particularly when use has been made of zinc nitrate as catalyst, which may decrease the stability to light of optical brightening agents.
• EXAMPLE 1 An aqueous solution of formaldehyde, containing 400 grams of formaldehyde per liter, is stabilized with methanol in per se conventional manner. The pH of the resultant formol solution (methanol-stabilized aqueous formaldehyde solution) is then adjusted to 9.5 by the gradual addition thereto of concentrated aqueous caustic soda solution.
• the obtained solution is then heated to about C., whereupon 600 grams of urea and then 750 grams of methyl carbamate are added. During the dissolution, the temperature of the mixture drops about 20 degrees; however, after the ensuing exothermic reaction has started, the temperature is soon brought up to its initial value. The reaction lasts about one hour.
• the solution is acidified up to pH 4, and is then heated to C. for one hour.
• Dihydroxymethylation is effected by adding 1.5 liters of formol solution (containing 400 grams of formaldehyde per liter and being stabilized with methanol), and then adding aqueous caustic soda solution to bring the pH up to 9.5.
• the reaction mixture is allowed to stand for about 12 hours, whereupon acidification is carried out until the pH is brought to neutrality.
• the piece of cloth is then mounted on a pin frame having the exact dimensions of the fabric prior to impregnation of the latter, the essential object of this operation being to avoid any shrinkage before thermofixation is effected and which, by altering the number of threads per unit area, might 'be the source of errors (higher readings) in resistance measurements.
• Drying and thermofixation are then carried out for 10 minutes at C. and for 4 minutes at 160 C., respectively.
• the finished piece of cloth After a simple rinsing with Water, followed by drying at 90 C. and conditioning (for 24 hours at 20 C. and 65% relative humidity), the finished piece of cloth has a warp and weft crease-recovery angle of 155 and 154 respectively (crease-recovery angles being determined according to ASTM D. 1424, 56 T). Measurements carried out on the treated piece of cloth, before drying, and untreated control, gave angle values of 146 and 94/ 86 respectively.
• the warp and weft average dynamometric resistance measured on 5 cm. wide test-pieces with a distance of 25 cm. between clips is 36.75 kg. and 28.6 kg., as against 57 kg. and 43 kg. for untreated cloth.
• Poplin specimens finished according to the present example were subjected to successive washings for 12 minutes each at 85 C. in a washing machine, in washwater containing 5 grams per liter of soap flakes. After 15 washes, the crease-recovery angles and warp and weft dynamometric resistance were maintained at 142/14,5 and 33 kg./25.6 kg. respectively. The washed specimens showed essentially no shrinkage (0.5 maximum). Moreover, the scorch test procedure produced minimal drop in warp resistance (only 4%).
• EXAMPLE 2 The pH of a formol solution, stabilized with methanol and containing 400 grams of formaldehyde per liter, is adjusted to 8.5. 600 grams of urea are added to 1.5 liters of such solution at ambient temperature (15 to 30 C.). After two hours reaction, 890 grams of ethyl carbamate are added to the reaction mixture, which is then acidified to pH. Reaction ensues for one hour at 50 C., after which 2.25 liters of the formol solution are added and the pH adjusted to 9. After several hours, the pH was down to 7 and the solution contained 425 grams per liter of 1,3 bis-hydroxymethyl-2-one 5 ethylcarboxylate-1,3,5-hexahydrotriazine.
• a piece of fabric similar to that employed according to Example 1 is treated under the same conditions as in the said example, in an aqueous finishing bath containing 165 grams per liter of the last-mentioned solution and 2 grams per liter of tartaric acid as catalyst.
• the warp and weft crease-recovery angles of the thustreated fabric are 146 and 150 respectively, and the dynamometric resistance is 35 kg. and 29 kg. respectively.
• EXAMPLE 3 750 grams of methyl carbamate are added to 2.25 liters of 400 g./liter-formol solution stabilized with methanol. The resultant solution (pH 9) is heated to 50 C. After one hours reaction at this temperature, 600 grams of urea are added to the reaction mixture, the pH adjusted to 4, and the reaction allowed to proceed for about one hour before adjusting the pH to 9.5. After about 12 hours standing at ambient temperature and neutralization, the solution contains 425 grams per liter of 1,3-bis-hydroxymethyl-2-one-S-methylcarboxylate 1,3,5 hexahydrotriazine.
• Poplin as described in Example 1 is subjected to the same treatment in an aqueous finishing bath containing Grams/ liter 425 g./liter-hydrotriazone solution 130 Zinc nitrate hexahydrate
• the pH of the finishing bath is adjusted to 4.8 before immersion impregnation therein of the piece of poplin, which is then squeezed down to 68% wet before being dried at 90 C. and subjected to thermofixation at 180 C. for 70 seconds.
• Cotton, wool, rayon, silk and other textile fabrics can be similarly finished.
• a textile finishing bath consisting essentially of an aqueous solution of a compound of the formula:
• a finishing bath according to claim 1, wherein the catalyst is an organic acid catalyst in an amount from 0.1% to 0.5% by weight.
• a finishing bath according to claim 1, wherein the catalyst is an inorganic metal salt of a strong acid in an amount from 0.5 to 4.0% by Weight.
• a finishing bath according to claim 4, wherein the catalyst is selected from the group consisting of tartaric acid, lactic acid and citric acid.
• a finishing bath according to claim 5, wherein the catalyst is selected from the group consisting of magnesium chloride, zinc nitrate and zinc chloride.

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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)

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Citations (4)

• 0
  • CH CH1044366D patent/CH1044366D/xx unknown
• 1965
  • 1965-07-19 FR FR25073A patent/FR1453931A/fr not_active Expired
• 1966
  • 1966-07-12 US US564540A patent/US3521996A/en not_active Expired - Lifetime
  • 1966-07-13 NL NL6609835A patent/NL6609835A/xx unknown
  • 1966-07-18 BE BE684275D patent/BE684275A/xx unknown
  • 1966-07-18 AT AT685666A patent/AT258853B/de active
  • 1966-07-19 GB GB32415/66A patent/GB1123322A/en not_active Expired
  • 1966-07-19 DE DE19661619133 patent/DE1619133A1/de active Pending

Patent Citations (4)

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