US3776767A - Process for improving the crease resistance and the abrasion resistance of a textile material - Google Patents

Process for improving the crease resistance and the abrasion resistance of a textile material Download PDF

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Publication number
US3776767A
US3776767A US00104142A US3776767DA US3776767A US 3776767 A US3776767 A US 3776767A US 00104142 A US00104142 A US 00104142A US 3776767D A US3776767D A US 3776767DA US 3776767 A US3776767 A US 3776767A
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United States
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temperature
process according
mol
cyanuric chloride
compound
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Expired - Lifetime
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US00104142A
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English (en)
Inventor
A Buehler
H Schuetz
D Maeusezahl
M Harris
C Guth
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BASF Schweiz AG
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Ciba AG
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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic and acyclic or carbocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/02—Polyureas
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides

Definitions

  • the reaction is then finalized at a temperature from 30 to 100 C, preferably from 45 to 70 C and, if desired, water is distilled out of the mixture formed.
  • the heterocyclic compound used as starting material in the present process must be practically colourless and contain at least one, preferably only one, heterocycle which may be altogether the only ring of the compound or, for example, may also contain a fused-on aromatic six-membered' ring.
  • Specially useful are compound with six-membered hetero rings, especially those whose ring contains 2 or 3 nitrogen atoms and 4 or 3 carbon atoms, such as pyridazine, pyrimidine, quinazoline and especially 1,3,5-triazine compounds. These compounds contain at least 2 halogen atoms linked with carbon atoms of the hetero ring, for example bromine or preferably chlorine atoms.
  • thiourea compound containing at least one hydrogen atom linked with nitrogen or preferably thiourea itself or an alkali metal or ammonium hydrogensulphide, as well as a monoalkanolamine or dialkanolamine containing l to 4 carbon atoms, preferably monoor diethanolamine.
  • the reaction is performed in an aqueous medium that may contain apart from water organic solvents, especially those which are water-miscible. There may be mentioned lower alcohols and acetone.
  • the reactions are performed within the temperature range from --l0 to +30 C; in the presence of an organic solvent the reaction temperature may be below 0 C, whereas when purely aqueous reaction media are used it is advantageous to react at 0 C or slightly higher.
  • reaction medium reveals a pH value of about 7.
  • the reaction is then finalized at a temperature from 30 to 100 C, preferably from 40 to 70 C, and may be terminated after 2 to 3 hours.
  • the pH value of the reaction mixture during this time should be within the neutral or slightly alkaline region. A dropin pH value impairs the solubility of the reaction product substantially and can be prevented by adding more alkali.
  • the condensates are also obtained, when in an aqueous medium at a temperature from 10 to +25?
  • a colourless heterocyclic compound that contains at least 2 nitrogen atoms in the hetero ring and at least 2 halogen atoms linked with carbon atoms of the hetero ring is reacted with a thiourea compound and on completion of this first reaction stage, without intermediate separation, for every mol of heterocyclic halogen compound used 0.5 to 1.5 mols ofa monoalkanolamine'are added, while maintaining a pH value from 6 to 10 and keeping the temperature of the reaction medium first for at least 8 hours at 30 to C and then for at least 5 hours at to C and, if desired, the water is distilled out of the mixture formed.
  • each of this halogen compound a total of about 4 mols of monoacidic base, thus for instance 3 mols of alkali metal hydroxide and lmol of alkanolamine, is consumed.
  • the amount of water used as reaction medium may be freely chosen within a wide range, advantageously so that, on one hand, the reaction mixtureis easy to stir from the start and the risk of heating beyond the prescribed temperature range is obviated and that, on the other hand, excessive dilution does not make the practical performance problematic.
  • the heterocyclic halogen compounds are sparingly soluble in the water serving as reaction medium, it is advantageous first to convert them into a finely distributed state, which can be done in known manner by dissolution in an organic watermiscible solvent such as acetone and pouring the solution out over ice,
  • the molecular ratio heterocyclic halogen compound sulphurcontaining compound should range from 1 2 to l 0.5, preferably from 1 11.5 to l 0.5
  • the molecular ratio of heterocyclic halogen compound alkanolamine should likewise be within the range from 1 2 to 1 0.5, preferably from 1 l.5 to l 0.5.
  • cyanuric chloride particularly good results are obtained by using equimolecular proportions or amounts of the three reactants differing only little therefrom.
  • the resulting product can be used as it is for thepurpose indicated above.
  • concentration of the mixture which is not very high at the end of the reaction, it is, however, advisable to remove the water completely or partially by distillation under vacuum. In this manner generally stable products are obtained which are at most only slightly tinted and are readily and completely soluble in water.
  • the products obtained by the process described above are suitable, as has already been said, for use in combination with aminoplasts in textile finishing, especially for improving the shape retention.
  • Particularly suitable for such a treatment is textile material of cellulose, if desired in combination with other fibres, for example polyester fibres. Therefore, according to a preferred use of the products of this invention textile materials are impregnated with an aqueous preparation containing a curable aminoplast precondensate, a curing catalyst and a condensate of the composition defined above, whereupon the textile material is dried and hardened by treatment at an elevated temperature.
  • Aminoplast precondensates are adducts of formaldehyde with methylolable nitrogen compounds.
  • amino-1,3,5- triazines such as N-substituted melamines, for example ammeline, guanamines, for example benzoguanamine or acetoguanamine.
  • symmetric alkyltriazones biuret, thiourea, alkylcarbamates, guanidine, alkylor aryl-ureas and -thioureas, alkylene ureas or diureas, for example ethyelne urea, propylene urea or acetylene diurea; 4,5-dihydroxy-imidazolidone-2 and its derivatives, for example the 4,5-dihydroxyimidazolidone-Z substituted in 4-position on the hydroxyl group by the residue CH CH CON- H-CH -OH.
  • methylol compounds of urea and of melamine are preferred and in the case of melamine compounds those ofa low or high degree of methylolation may be used. It is also possible to use compounds whose methylol groups are more or less completely etherified, for example, with methyl groups.
  • the conventional acid or potentially acid compounds may be used, such as ammonium chloride, magnesium chloride or zinc fluoroborate.
  • the preparation used for finishing the textile materials contains in addition to the aminoplast precondensate, the curing agent and the condensate of this invention also an emulsion polymer prepared from an N- methylolamide of an a,B-ethylenically unsaturated carboxylic acid or an ether of such a methylolamide and an alkaline earth metal salt of an a,,B-ethylenically unsaturated monocarboxylic acid, especially the copolymers, obtained in an aqueous emulsion, from a. 0.25 to percent by weight of an alkaline earth metal salt of an a,,B-ethylenically unsaturated monocarboxylic acid (for example calcium acrylate),
  • an alkaline earth metal salt of an a,,B-ethylenically unsaturated monocarboxylic acid for example calcium acrylate
  • an N- methylolamide or N-methylolamide ether of an a,B-unsaturated monoor dicarboxylic acid for example acrylic acid methylolamide, methacrylic acid methylolamide or the methyl ethers of these methylolamides
  • At least one further copolymerizable compound for example an ester of acrylic or methacrylic acid and an alkanol such as methanol, ethanol, n-butanol, acrylic acid tertiary butylamide, vinylidenechloride, vinylacetate, acrylonitrile, styrene.
  • an ester of acrylic or methacrylic acid and an alkanol such as methanol, ethanol, n-butanol, acrylic acid tertiary butylamide, vinylidenechloride, vinylacetate, acrylonitrile, styrene.
  • aqueous preparations may contain further ingredients, for example hydrophobizing agents, suitable optical brighteners, wetting agents, dispersants or flameproofing agents, especially phosphorus compounds such as dialkylphosphono-propionic acid methylolamides.
  • hydrophobizing agents for example hydrophobizing agents, suitable optical brighteners, wetting agents, dispersants or flameproofing agents, especially phosphorus compounds such as dialkylphosphono-propionic acid methylolamides.
  • suitable optical brighteners especially wetting agents, dispersants or flameproofing agents, especially phosphorus compounds such as dialkylphosphono-propionic acid methylolamides.
  • a nonionic agent that produces a soft handle
  • aqueous emulsion of a methylolmelamine alkyl ether modified by stearic acid alkylolamide residues for example an aqueous emulsion of a methylolmelamine alkyl ether modified by stearic acid alkylolamide residues.
  • the proportions of the ingredients of the aqueous preparations may vary within wide limits and may be adapted to the purpose in hand. In general it is indicated to use for 10 parts of aminoplast precondensate 1 to 4 parts of condensate from heterocyclic halogen compound, thiourea and alkanolamine. Otherwise, the textile material may be treated in the usual manner.
  • undyed or dyed fabric or tricot may be impregnated on a padder with the preparation and, advantageously after an intermediate drying operation at a temperature of up to 100 C, subjected to a treatment with dry heat of l-l80 C for 2 to 20 minutes, the temperature and the duration of the treatment being adapted to the purpose of the treatment which may be, for example, an improvement of the wet fastness properties for direct dyeing dyestuffs, an anti-crease finish or permanent shaping (permanent press).
  • the finishing operation may also be combined with a dyeing operation, for example so that the impregnating solution further contains a dyestuff which, by virtue of special substituents, is reactive towards the fibre or more especially towards the aminoplast precondensate and, by virtue of this property, is fixed on the substrate during the heat treatment or even before it.
  • a dyestuff which, by virtue of special substituents, is reactive towards the fibre or more especially towards the aminoplast precondensate and, by virtue of this property, is fixed on the substrate during the heat treatment or even before it.
  • an aminoplast resin finish impairs the mechanical properties of cellulosic fibrous materials, especially their tensile strength and abrasion resistance; in general the loss in strength is the greater the higher the content of aminoplast and the more energetic the hardening is.
  • these serious drawbacks can be substantially prevented with the aid of the new condensates or at least they can be reduced to an acceptable degree.
  • these condensates improve the soil release from the fibre.
  • Example 1 A solution of 190 g (1 mol) of cyanuric chloride in 1 litre of acetone is poured over a mixture of 1 litre of water and 1 kg of ice and the precipitated cyanuric chloride is filtered off. The paste is introduced into a solution which has been prepared at C from 76 g (1 mol) of thiourea and one-half litre of water and has then been cooled by adding one-half kg of ice. By dropping in a 5N-sodium hydroxide solution the pH value is maintained at 6.7 to 6.9 during this first condensation stage and the temperature is maintained at 8 to 10 C by indirect cooling.
  • Example 3 A suspension of 18.5 g (0.1 mol) of cyanuric chloride in 100 ml of alcohol is cooled to 5 to 10 C. One lot of 6.1 g (0.1 mol) of monoethanolamine is added; dur ing minutes m1 of SN-sodium hydroxide solution (0.1 mol) are dropped in and the reaction mixture is stirred for about 1 hour at the same temperature until a constant pH value of about 2.7 has been established.
  • Example 4 v 18.5 Grams (0.1 mol) of cyanuric chloride are suspended in 200 ml of a mixture of 100 ml of water and 100 ml of acetone and at 0 C 6.1 g (0.1 mol) of monoethanolamine are added in one lot. By dropping in 5.3
  • Example 5 A suspension of 18.5 g (0.1 mol) of cyanuric chloride in ml of water is mixed within 60 minutes at 0 C with 14.35 ml (0.1 mol) of a 39.1 percent solution of sodium hydrosulphide.
  • the resulting yellow suspension is mixed' at room temperature with 6.1 g (0.1 mol) of monoethanolamine and then with one lot of 20 ml (0.1 mol) of 5N-sodium hydroxide solution.
  • the batch is then heated to 50 C and heated and stirred at this temperature for about 2 hours. After this time the reaction mixture reveals a pH value of about 7.
  • Example 6 Aqueous padding liquors are prepared with the use of the substances listed below:
  • Example 7 Mercerized cotton popelin is impregnated with the liquors of this composition, then dried at 60 to 80 C and heated for 13 minutes at 170 C. The fabric is then washed for 5 minutes in a boiling 0.2 percent sodium carbonate solution, rinsed in cold water and dried.
  • Example 8 Aqueous padding liquors are prepared with the use of the under-mentioned substances:
  • Aminoplast precondensate 50 percent aqueous solution ofa mixture of dimethylol-ethylene urea and methyl ether of a highly methylolated melamine.
  • Brightening agent of the formula S OaNa (LCM f.
  • Mercerized and bleached cotton popelin is impregnated with padding liquors composed as shown in Tables IV, V and V1 to a weight increase of 60 percent referred to the original weight of the fabric. After having been dried at 60 to 80 C the fabric is heat-treated for 4% minutes at C, then washed for 5 minutes in a boiling 0.2 percent sodium carbonate solution, rinsed in cold water and dried.
  • aminoplast precondensate is a methylol compound of urea or melamine.
  • the impregnating the textile material condensation product is obtained by reacting cyanuric chloride with A. thiourea in an aqueous medium at a temperature from about- 10 to 25 C and at a-pH- value from 6 to 9 at a molecular ratio of 121.5 to 1:0.5 and, without intermediate separation with (B) 0.5 to 1.5 mols of a monoalkanolamine with l to 4 carbon atoms for every mol of cyanuric chloride, maintaining a pH-value from 6 to 10, keeping the temperature of the reaction for at least 8 hours at 30 to 50 C and then for at least 5 hours at 60 to 65 C, and removing water from the resulting mixture by distillation.
  • the aminoplast precondensate comprises an adduct of formaldehyde with a nitrogen compound reactable therewith to form an N-methylol group
  • the curing catalyst is an acid or potentially acid compound
  • drying is effected at a temperature up to 100 C and heating is effected with dry heat at a temperature from to C for 20

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US00104142A 1967-10-24 1971-01-05 Process for improving the crease resistance and the abrasion resistance of a textile material Expired - Lifetime US3776767A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1482667A CH480488A (de) 1967-10-24 1967-10-24 Verwendung von Kondensationsprodukten zum Veredeln von Textilmaterialien

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US3776767A true US3776767A (en) 1973-12-04

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US (1) US3776767A (de)
BE (1) BE722763A (de)
CH (2) CH469043A (de)
CS (1) CS151484B2 (de)
FR (1) FR1595640A (de)
GB (1) GB1235307A (de)
IL (1) IL30837A (de)
NL (1) NL6815153A (de)
SE (1) SE340888B (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020037410A1 (en) * 2000-08-04 2002-03-28 Christian Criegee Flameproof finishing of cellulose, fibers and articles containing them
CN113584883A (zh) * 2021-07-16 2021-11-02 江苏华佳丝绸股份有限公司 一种制备抗皱真丝织物的方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2561973A (en) * 1949-04-30 1951-07-24 Monsanto Chemicals Formaldehyde-urea condensation
US2573525A (en) * 1947-06-11 1951-10-30 American Cyanamid Co Thermosetting compositions comprising aminoplast and chlorotriazines
US2684346A (en) * 1950-07-29 1954-07-20 Monsanto Chemicals Latent curing catalysts and compositions containing same
US2990298A (en) * 1957-06-24 1961-06-27 Ici Ltd Textile treatment process
US3028264A (en) * 1959-04-02 1962-04-03 Jr John G Frick Wrinkle resistance treatment for cellulosic textile materials
US3054792A (en) * 1956-06-15 1962-09-18 Ici Ltd New triazino nitro dyestuffs

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573525A (en) * 1947-06-11 1951-10-30 American Cyanamid Co Thermosetting compositions comprising aminoplast and chlorotriazines
US2561973A (en) * 1949-04-30 1951-07-24 Monsanto Chemicals Formaldehyde-urea condensation
US2684346A (en) * 1950-07-29 1954-07-20 Monsanto Chemicals Latent curing catalysts and compositions containing same
US3054792A (en) * 1956-06-15 1962-09-18 Ici Ltd New triazino nitro dyestuffs
US2990298A (en) * 1957-06-24 1961-06-27 Ici Ltd Textile treatment process
US3028264A (en) * 1959-04-02 1962-04-03 Jr John G Frick Wrinkle resistance treatment for cellulosic textile materials

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020037410A1 (en) * 2000-08-04 2002-03-28 Christian Criegee Flameproof finishing of cellulose, fibers and articles containing them
CN113584883A (zh) * 2021-07-16 2021-11-02 江苏华佳丝绸股份有限公司 一种制备抗皱真丝织物的方法

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Publication number Publication date
GB1235307A (en) 1971-06-09
DE1803087A1 (de) 1969-06-19
CH1482667A4 (de) 1969-03-31
CS151484B2 (de) 1973-10-19
NL6815153A (de) 1969-04-28
IL30837A0 (en) 1968-12-26
FR1595640A (de) 1970-06-15
DE1803087B2 (de) 1975-07-03
IL30837A (en) 1972-07-26
CH480488A (de) 1969-12-15
SE340888B (de) 1971-12-06
BE722763A (de) 1969-04-23
CH469043A (de) 1969-02-28

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