EP0242495B1 - Fleckenabweisende Nylonteppiche - Google Patents

Fleckenabweisende Nylonteppiche Download PDF

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Publication number
EP0242495B1
EP0242495B1 EP86870055A EP86870055A EP0242495B1 EP 0242495 B1 EP0242495 B1 EP 0242495B1 EP 86870055 A EP86870055 A EP 86870055A EP 86870055 A EP86870055 A EP 86870055A EP 0242495 B1 EP0242495 B1 EP 0242495B1
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EP
European Patent Office
Prior art keywords
carpet
units
nylon
condensation product
stain
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP86870055A
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English (en)
French (fr)
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EP0242495A1 (de
Inventor
Randolph Compton Blyth
Pompelio Angelo Ucci
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Co
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Monsanto Co
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Filing date
Publication date
Priority to US06/768,302 priority Critical patent/US4592940A/en
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to EP86870055A priority patent/EP0242495B1/de
Priority to DE8686870055T priority patent/DE3673008D1/de
Priority claimed from US06/914,507 external-priority patent/US4680212A/en
Publication of EP0242495A1 publication Critical patent/EP0242495A1/de
Priority claimed from US07/370,099 external-priority patent/US4892558A/en
Priority to US07/457,201 priority patent/US5182154A/en
Priority claimed from US07/457,201 external-priority patent/US5182154A/en
Publication of EP0242495B1 publication Critical patent/EP0242495B1/de
Application granted granted Critical
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • 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
    • D06M15/41—Phenol-aldehyde or phenol-ketone resins
    • D06M15/412—Phenol-aldehyde or phenol-ketone resins sulfonated
    • 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
    • D06M15/63—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing sulfur in the main chain, e.g. polysulfones

Definitions

  • nylon carpet means carpet in which the yarn used in making the pile fabric thereof consists essentially of nylon yarn
  • the term “yarn” means a continuous strand of fibers
  • the term “fibers” includes fibers of extreme or indefinite length (i.e. filaments) and fibers of short length (i.e., staple).
  • stain resistant when used herein with reference to carpet means carpet having the ability to resist staining when subjected to Food, Drug and Cosmetic Red Dye No. 40 (herein after referred to as Red Dye 40) under the conditions set forth in the Stain Resistance Test given hereinafter. Briefly, the test involves subjecting a test sample of carpet to two standard washing cycles in a conventional washing machine and then immersing the sample in a solution containing Red Dye No. 40. If the carpet is not visibly stained by the dye under the test conditions, the carpet is stain resistant within the meaning of the term as used herein. The purpose of the test is to identify carpets having durable and lasting resistance to staining normally caused by Red Dye 40.
  • Red Dye No. 40 is an acid dye having the following structure:
  • Nylon carpet is a popular floor covering for both residential and commercial applications. Such carpeting is relatively inexpensive and offers a desirable combination of qualities, such as aesthetics, comfort, safety, warmth and quietness. Also, it is available in a wide variety of attractive colors, patterns and textures. However, nylon carpet is permanently stained by most artificial colourants normally added to foods, berages, medicines, cosmetic, etc., the most common of which is Red Dye No. 40.
  • EP-A 235 989 (not published at the filling date of the present application) describes polyamide fibres made stain-resistant by treating them with a sulphonated naphtolor sulphonated phenol-formaldehyde condensation product.
  • US-A 4 501 591 describes imparting stain resistance to polyamide carpets during a continuous dyeing process, which involves adding to the dye liquor an alkali metal silicate and a sulphonated phenol-formaldehyde condensation product.
  • the present invention provides stain resistanc nylon carpet and a process for obtaining such carpet,
  • the process comprises immersing a carpet having a pile made from nylon yarn in an aqueous solution of a polymeric condensation product consisting essentially of repeating units of the formula where R is the same or different in each unit and is hydrogen or a radical selected from the group consisting of-SOaX, proviso that at least 40% of the total units contain an ⁇ SO ⁇ X radical and at least 40% of the total units contain the linkage, wherein X is H or a cation, e.g.
  • the weigth ratio of aqueous solution to nylon yarn is in the range of 20:1 to 40:1, the pH of the solution is no greater than 4.5, the temperature of the solution is at least 95 ° C and the amount of the condensation product in the solution is sufficient to provide a carpet coated with from 0.1 % to 1.0% of the condensation product based on the weight of nylon yarn.
  • the amount of the polymeric condensation product is preferably from 0.3% to 1.0% based on the weight of nylon fibre. At concentrations above about 1.0% on weight of fibre the fibres become stiff and impart a harsh and undesirable hand to the carpet.
  • carpet treated in accordance with the present invention can be sheared in a conventional manner (i.e., as the last step in the carpet making process) to provide a cut pile carpet in which the freshly exposed pile fibre ends are stain resistant without further treatment. This is important since further treatment of the carpet after the shearing step were required to achieve stain resistance of the exposed ends, such treatment would add significantly to the overall cost of the carpet and, therefore, be undesirable.
  • the aqueous solution should be maintained at a pH no greater than about 4.5 and at a temperature at least about 95 ° C, otherwise, the carpet does not pick up sufficient condensation product to impart stain resistance thereto.
  • the aqueous solution is maintained at a pH of 4.5 at the boil.
  • the ratio of aqueous solution to carpet fibre should be within the range of 20:1 to 40:1. It has been dicovered that in carrying out the process at a ratio of about 20:1 and with the slution at a pH of 4.5 and at the boil, about 40% to 50% of the condensation product is picked up by the immersed carpet in about 30 minutes.
  • the aqueous solution must contain 0.25 to 2.5%, based on the weight of carpet fiber, (a 100 to 150% excess) of the product in order to coat the carpet with a sufficient amount of the product (0.1 to 1.0% on weight of fiber) to impart stain resistance thereto.
  • the exact amount of the excess required in a given instance will depend on the particular processing conditions selected and can be easily determined by routine experimentation.
  • Water-soluble condensation products useful in practicing the process of the present invention may be prepared by the condensation of formaldehyde with one or more phenols selected from the group consisting of (i) diphenolsulfone, (ii) diphenolsulfone sulfonic acid or salt thereof and (iii) phenolsulfonic acid or salt thereof, with the phenols being selected so that at least 40% of the phenols contain the group consisting of (i) diphenolsulfone, (ii) diphenolsulfone sulfonic acid or salt thereof and (iii) phenolsulfonic acid or salt thereof, with the phenols being selected so that at least 40% of the phenols contain the group consisting of (i) diphenolsulfone, (ii) diphenolsulfone sulfonic acid or salt thereof and (iii) phenolsulfonic acid or salt thereof, with the phenols being selected so that at least 40% of the phenols contain the group consisting of (i) diphenolsul
  • sulfonic acid radical or salt thereof contain a sulfonic acid radical or salt thereof.
  • Representative salts of the sulfonic acids include the alkali metal salts, such as sodium and potassium, and the ammonium salt and may be obtained by neutralizing the sulfonic acid with a base such as sodium, potassium or ammonium hydroxide.
  • Condensation products prepared from monosulfonic acids have been found to impart better stain resistance to the carpet than corresponding products prepared from di-or trisulfonic acids and, therefore, are preferred with p-phenolsulfonic acid and 4,4-diphenolsulfone-2-sulfonic acid being particularly preferred.
  • Representative condensation products include the product having repeating units of the formulas where the product ratio of (A) to (B) is 60 to 40 and the product having repeating units of the formulas where the ratio of units (C) to (D) is at least 8:1 and preferable as high as possible with products in which all of units are units (C) being preferred.
  • the molecular weight and the monosulfonate content of the water-soluble condensation product preferably is as high as possible, for example, a molecular weight ranging from 400 to 800 with a monosulfonate content of 100% or as near 100% as possible.
  • the water solubility of the condensation product is influenced by the type of terminal groups present in its structure, for example, hydrophylic groups such as -CH 2 0H and -CH 2 S0 3 H render the product more water soluble than groups, such as methyl groups.
  • the condensation products may conveniently be prepared by methods known in the art, for example, by condensation of the phenols with formaldehyde in an acid or alkaline medium at elevated temperatures.
  • an acid medium from 0.3 to 0.5 mole of formaldehyde is used for each mole of phenol and, in a basic medium, from 0.9 to 1.5 moles of formaldehyde is used for each mole of phenol.
  • the basic condensation provides products having a greater proportion of terminal -CH 2 0H groups and, therefore, greater water-solubility.
  • the nylon carpet is treated during beck dyeing operations, by lowering the pH of the beck dye bath from its normal range of 6.5 to 8.0, to 4.5 or lower.
  • nylon carpets of major commercial importance are those having pile fibers shaped from nylon 66 which is polyhexamethylene adipamide and those shaped from nylon 6 which is polycaprolactam.
  • other nylons from which the pile fibers may be shaped include nylon 11 which is the polymer of 11-amino undecanoic acid, nylon 610 which is polyhexamethylene sebacamide; and copolymers of nylon 66 or nylon 6, for example, a nylon 66/6 copolymer or nylon 66/6TA copolymer where 6TA is hexamethylene terephthalamide.
  • a 5 cm x 5 cm sample of carpet is subjected to two wash cycles in a heavy-duty Sears and Roebuck electric washing machine Model No. 111.7114802.
  • Detergent 100-150 gms
  • ALL@ Lever Brothers Company under the tradename ALL@
  • the settings on the machine are as follows: the fabric setting is Cotton, Linen, Colored; the wash-rinse setting is Warm (48 ° C) Wash/Cold Rinse; the water level setting is Low; and the wash cycle setting is 14 Minute Wash Cycle.
  • washing machine and detergent specified, and equivalent washing machine and/or detergent may be used.
  • the sample is removed from the washing machine and immersed in an aqueous solution of cherry flavoured soft drink premex containing FDC Red Dye No. 40 in which the concentration of the dye is 0.054 gms/liter.
  • the carpet sample is left immersed in the solution for one hour.
  • the sample is then removed from the solution and washed with tap water. If the sample is not visibly stained by the dye, it is characterized as being stain resistant within the meaning of the expression as it is used herein.
  • cut pile tufted carpets were prepared from polyamide fibers and treated in accordance with the process of the present invention.
  • the treated carpets were then tested to evaluate their resistance to staining by various colorants presents in common household substances.
  • a 310 filament, 60 denier (6.7 Tex) per filament (dpf), undrawn nylon 66 yarn was prepared by conventional procedures. Fifty-four (54) such yarns were combined to form a tow having a total denier of about 1,000,000 (111111 Tex). The tow was drawn over rolls to provide nominal 18 dpf tow (20d Tex per filament), crimped in a conventional stuffer box and cut into 7 inch (19.05 cm) staple. The staple was carded, drafted and spun on a conventional ring spinning frame to provide a 2-4cofton count yarn having about 4.5 tpi (177 tpm) of twist in the Z-direction.
  • Two of these yarns were plied on a conventional ring twister to provide a plied yarn having a net twist of 0 tpi in the Z-direction and 3 tpi (118 tpm) in the S-direction.
  • the resulting plied yarn was then heatset.
  • Two cut pile tufted carpets were made from the heatset plied staple yarn and dyed to a light gold color in a conventional beck dyeing operation in which the carpet was immersed in an aqueous dye bath contained within a vessel. The bath was maintained at a pH of 6.5 and at the boiling temperature of the bath (liquor). The weight ratio of liquor to carpet fiber was 20:1.
  • Light gold was selected as being a color which contrasts well with most stains.
  • the liquor was then drained from the dye vessel and replaced with a corresponding amount of water.
  • a water-soluble product formed by the acid condensation of 4,4'-diphenolsulfone, p-phenolsulfonic acid and formaldehyde in which the mole ratio of sulfone to sulfonic acid is about 60:40 was added to the vessel and dissolved in the water in an amount sufficient to provide 0.4% by weight of condensation product on weight of carpet pile fabric.
  • the resulting solution was adjusted to a pH of 4.5 by the addition of an appropriate amount of acetic acid thereto.
  • the solution was then brought to the boil and one of the carpets was immersed (treated) therein for a period of 30 minutes.
  • the treated carpet (invention) and untreated carpet (control) were then sheared (i.e., defuzzed) and used in conducting the following tests.
  • Samples of the treated and untreated (control) carpets were subjected to the common household liquid substances listed in the table below to determine the resistance of the samples to staining by colorants present in these substances. Each substance was applied to the carpet sample, rubbed into the carpet, left on the sample overnight and, finally, the next day the sample was washed to remove the substance, first with a dilute water solution of a commercial detergent and then with water.
  • test B the substance which most severely and permanently stained the untreated carpet samples was the soft drink (cherry flavored) containing Red Dye 40 in a concentration of 0.054 gms/liter.
  • a separate test was conducted to determine the effect of a massive spill of the soft drink on a sample of the treated carpet.
  • one gallon (3785 ml) of the soft drink was poured onto an appropriate sized carpet sample from a gallon milk container, the container being held at a height of one meter above the face of the carpet sample. The soft drink was left on the carpet sample overnight. No steps were taken to clean the carpet or remove any of the soft drink until the next day. The next day the carpet sample was cleaned in the manner described above. Surprisingly, after being cleaned, no visual evidence of the soft drink (Red Dye 40) remained on the carpet sample.
  • Fiber samples taken from the treated and untreated carpets were tested to determine the ability of the fibers to resist staining by the above soft drink.
  • the optical density of a weighed amount of soft drink containing FD&C Red Dye No. 40 was measured on a Carey 15 Spectrophotometer using a cm cell with the light absorption being measured at 520 millimicrons. (Light absorption is a measure of dye concentration of the drink.)
  • the drink was prepared as before according to the instructions on the package containing the premix ingredients.
  • the drink was prepared as before according to the instructions on the package containing the premix ingredients.
  • the light absorption reading was recorded as To.
  • the soft drink was put into a stoppered container with a sufficient amount of fiber sample to provide a weight ratio of drink to fiber of 40:1.
  • the stoppered container of drink and fiber was then shaken on a motorized shaker for a period of two hours.
  • the fiber was then removed from the container and the optical density of the drink was determined as before. The reading this time was recorded as Ti.
  • test results were expressed as a change in light penetration, expressed as a percentage, calculated as follows:

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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)

Claims (6)

1. Verfahren zur Erzeugung von Fleckenunempfindlichkeit bei einem Teppich mit einem aus Nylongarn hergestellten Flor, dadurch gekennzeichnet, daß man den Teppich in eine wäßrige Lösung aus einem Polymerkondensationsprodukt aus im wesentlichen sich wiederholenden Einheiten der Formel
Figure imgb0017
worin R gleich oder verschieden in jeder Einheit ein Wasserstoffatom oder eine Gruppe der Gruppe mit den Formeln -S03X,
Figure imgb0018
mit der Maßgabe bedeutet, daß mindestens 40% der Einheiten eine Gruppe der Formel -S03X und mindestens 40% der Einheiten die Verknüpfung der Formel
Figure imgb0019
enthalten, worin X ein H-Atom oder ein Kation bedeuten, eintaucht und das Gewichtsverhältnis von wäßriger Lösung zu Nylongarn im Bereich von 20:1 bis 40:1 liegt, der pH-Wert der Lösung nicht größer als 4,5 ist, die Temperatur der Lösung mindestens 95°C beträgt und die Menge des Kondensationsprodukts in der Lösung zur Herstellung eines mit 0,1 bis 1,0% des Kondensationsprodukts, bezogen auf das Gewicht des Nylongarns, beschichteten Teppichs ausreicht.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die wäßrige Lösung auf dem Siedepunkt hält.
3. Verfahren nach Anspruch 1 oder Anspruch 2, dadurch gekennzeichnet, daß man den Teppich mit 0,3 bis 1,0% des Kondensationsprodukts, bezogen auf das Gewicht des Nylongarns, beschichtet.
4. Verfahren nach einem der vorangegangenen Ansprüche, dadurch gekennzeichnet, daß R in mindestens 40% der Einheiten als Gruppe der Formel
Figure imgb0020
vorliegt und in den restlichen Einheiten als Gruppe der Formel -SOsH oder Salz davon vorliegt.
5. Verfahren nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß R in mindestens 80% der Einheiten als Gruppe der Formel
Figure imgb0021
vorliegt und in den restlichen Einheiten R als Gruppe der Formel
Figure imgb0022
voliegt.
6. Verfahren nach einem der vorangegangenen Ansprüche, dadurch gekennzeichent, daß das Gewichtsverhältnis 20:1 beträgt.
EP86870055A 1983-12-16 1986-04-25 Fleckenabweisende Nylonteppiche Expired - Lifetime EP0242495B1 (de)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US06/768,302 US4592940A (en) 1983-12-16 1985-08-22 Stain-resistant nylon carpets impregnated with condensation product of formaldehyde with mixture of diphenolsulfone and phenolsulfonic acid
EP86870055A EP0242495B1 (de) 1983-12-16 1986-04-25 Fleckenabweisende Nylonteppiche
DE8686870055T DE3673008D1 (de) 1983-12-16 1986-04-25 Fleckenabweisende nylonteppiche.
US07/457,201 US5182154A (en) 1983-12-16 1989-12-26 Stain resistant nylon carpets

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
US56237083A 1983-12-16 1983-12-16
US64360684A 1984-08-23 1984-08-23
US83480486A 1986-03-06 1986-03-06
EP86870055A EP0242495B1 (de) 1983-12-16 1986-04-25 Fleckenabweisende Nylonteppiche
US06/914,507 US4680212A (en) 1986-03-06 1986-10-02 Stain resistant nylon fibers
US5971487A 1987-06-08 1987-06-08
US8477787A 1987-08-13 1987-08-13
US29630189A 1989-01-09 1989-01-09
US07/370,099 US4892558A (en) 1986-03-06 1989-06-21 Process for dyeing stain resistant nylon carpets
US07/457,201 US5182154A (en) 1983-12-16 1989-12-26 Stain resistant nylon carpets

Publications (2)

Publication Number Publication Date
EP0242495A1 EP0242495A1 (de) 1987-10-28
EP0242495B1 true EP0242495B1 (de) 1990-07-25

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EP86870055A Expired - Lifetime EP0242495B1 (de) 1983-12-16 1986-04-25 Fleckenabweisende Nylonteppiche

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Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03500189A (ja) * 1988-02-01 1991-01-17 アライド‐シグナル・インコーポレーテッド 敷設カーペットに対する汚染防止剤の適用
CA2046966A1 (en) * 1990-07-14 1992-01-15 Rudolf Ehrler Soil-repellent treatment of textile material made of nylon or wool
DE4223830A1 (de) * 1992-07-20 1994-01-27 Sandoz Ag Schmutzabweisendes Ausrüstungsmittel

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0235989A1 (de) * 1986-02-14 1987-09-09 E.I. Du Pont De Nemours And Company Verfahren zum Herstellen von faulabweisenden Polyamidfasern

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1062949A (fr) * 1952-09-13 1954-04-28 Composition pour le nettoyage et la régénération des fils de superpolyamide
CH464141A (de) * 1966-06-03 1968-07-15 Ciba Geigy Verfahren zum Bedrucken von Textilmaterial aus synthetischen Polyamidfasern
US4501591A (en) * 1983-12-27 1985-02-26 Monsanto Company Process for conveniently providing stain-resistant polyamide carpets

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0235989A1 (de) * 1986-02-14 1987-09-09 E.I. Du Pont De Nemours And Company Verfahren zum Herstellen von faulabweisenden Polyamidfasern

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