US3424680A - Soil retardant compositions and textile materials - Google Patents

Soil retardant compositions and textile materials Download PDF

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Publication number
US3424680A
US3424680A US477575A US3424680DA US3424680A US 3424680 A US3424680 A US 3424680A US 477575 A US477575 A US 477575A US 3424680D A US3424680D A US 3424680DA US 3424680 A US3424680 A US 3424680A
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United States
Prior art keywords
soil
carpets
carpet
dihydroxypropyl
pile
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US477575A
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English (en)
Inventor
William Julius Van Loo Jr
George Robert De Paolo
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Wyeth Holdings LLC
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American Cyanamid Co
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/402Amides imides, sulfamic acids
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/23907Pile or nap type surface or component
    • Y10T428/23986With coating, impregnation, or bond
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated 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
    • Y10T442/2279Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric

Definitions

  • compositions effective for imparting soil retardance to textiles which comprise a compound of the formula R-C-NHCHzCHOHCHzOH wherein R is selected from the group consisting of alkyl, alkenyl and alkadienyl having from about 12 to 22 carbon atoms, said compound being dispersed in an alcoholic solution or in an aqueous solution with an imidazolinium compound such as N-(2,3-dihydroxypropyl)-N-(2-hydroxyethyl)-2 heptadecylimidazolinium chloride.
  • the invention also includes a method of imparting soil retardance to carpets by application of the composition and carpet fabrics having thereon the dry residue of the composition.
  • This invention relates to compositions useful for imparting soil retardance to textile materials, to methods of rendering textile materials soil retardant and to the resultant soil retardant textiles.
  • the invention pertains to compositions and methods effective for improving the resistance to soiling or for reducing the adherence or attraction of soil particles to textile materials such as fiat or pile carpets.
  • Soil retardants heretofore used or suggested include colloidal dispersions of inorganic oxides, such as silica, alumina, titania, and the like. These inorganic colloids are useful to some degree but have short service life, especially when carpets treated therewith are vacuumed. The inorganic colloids also cause discoloration or whitening of the treated carpets so that an undesirable change in shade occurs even before the carpet is put into service use.
  • soil retardants of organic nature have been employed. This type also suffers from deficiencies including one or more of the following, depending on the specific organic variety: (1) not universally effective on carpets of all fiber types; (2) impart stiffness or rigidity to the carpet pile resulting in undesirable hand or lie of such pile and embrittlement thereof; (3) cause discoloration or whitening of the carpet leading to an undesirable change in shade even before service use; (4) lack reasonable durability to service use and cleaning, particularly when vacuuming; (5) require uneconomical usage levels for effectiveness.
  • soil retardants which are effective on carpets of all fiber types and which overcome the deficiencies of the prior art soil retardants.
  • An object of the invention is to provide compositions of matter useful for imparting durable soil resistance or retarda-uce to textile materials, particularly flat or pile carpets of all types, without causing discoloration or rigidity.
  • Another object of the invention is to provide a method for imparting durable soil retardance to textile materials such as flat or pile carpets.
  • a further object of the invention is to provide soil retardant textiles, particularly carpets of all fiber types and color, which also substantially retain their original coloration and hand, even after repeated vacuumings.
  • Compounds of this class useful for imparting soil retardance include:
  • Compounds of Formula I may be applied to fibrous materials as alcoholic solutions, alcohol-Water solutions, or as aqueous dispersions employing imidazolinium compounds as dispersants, with or without a Water-soluble alcohol.
  • suitable alcohols include watersoluble or substantially water-insoluble alcohols.
  • Effective water-osluble alcohols are methanol, ethanol, propanol, isopropanol, and the like, and effective substantially Water-insoluble alcohols include tertiary butanol, hexanol, and the like.
  • Sufficient alcohol or alcohol-water mixture should be employed to dissolve or disperse the amide. Generally, in alcohol-water mixtures, the alcohol should comprise at least 25% by weight of solvent.
  • the imidazolinium dispersants are quaternary cationic imidazolinium salts of the formula H2C wherein R is higher alkyl, i.e., having at least 8 carbon atoms and preferably from 12 to 22 carbon atoms; R and R are each selected from the group consisting of hydroxyand polyhydroxy-substituted alkyl; and X is an anion, preferably halogen but also including N0 1 SO H methosulfates, e.g., CH OSO and the like. R and R may be the same or different and preferably contain 1 to 7 carbon atoms, .i.e., lower alkyl.
  • a particularily effective cationic imidazolinium dispersant is N- (2,3 dihydroxypropyl N (2 hydroxyethyl) 2 heptadecylimidazoliniurn chloride.
  • the amide and imidazolinium dispersant may be employed in an amidezdispersant ratio of from 2:1 to 35:1, preferably 3:1 to :1, together with sufficient water or water-alcohol mixture for the desired fluidity.
  • an amidezdispersant ratio of from 2:1 to 35:1, preferably 3:1 to :1, together with sufficient water or water-alcohol mixture for the desired fluidity.
  • a preferred range under these conditions is 24:1 to :1, same basis.
  • the compounds may effectively be applied to materials containing fibers of all types, natural and synthetic, singly or as blends.
  • fibers include cotton, rayon, wool, nylon, acrylics, polyesters, and the like.
  • the fibers are in the form of a carpet with loop or out pile.
  • carpets may contain a backing material of known composition and, additionally, may have whatever backing treatment is appropriate.
  • the backing material may be jute (burlap), alone or impregnated with known resins, and may be further supported with nonslip foam rubber.
  • Flat or hooked carpets are also made soil retardant in accordance with the invention.
  • the treating compositions are applied to finished fibrous textile materials or during manufacture thereof any suitable means such as dipping, padding, spraying, coating, and the like.
  • spraying is the preferred technique, although mechanical applicators may be used on previously installed carpeting.
  • the amount of solids of the composition applied to the fibrous material is not critical and may vary from about 0.1 to about 10.0% based on the weight of the fibrous material.
  • the amount of solids applied to carpet pile will be between 0.25 and 5.0% based on the weight of said pile.
  • the treating composition should contain sufiicient solids to deposit the required amount on the fibrous material by the particular application method employed.
  • the fibrous material is allowed to dry so as to remove the alcohol and/or water. Drying may be accomplished at ambient conditions or, where possible, at elevated temperatures.
  • ovens circulating hot air at about 140 F. has been found particularly advantageous. The time required for drying in such ovens is about four hours.
  • the amides of Formula I are useable as crude reaction mixtures directly from the reaction medium from which they are prepared, thus avoiding the expense of additional processing, although purified products may be used, if desired.
  • the amides alone, or in admixture with the imidazolinium dispersants may be transported as a dry powder and thereafter, at place of use, dissolved or dispersed as described to form the treating compositions.
  • the effective soil retardance imparted by the combination of amide and imidazolinium salt is an unexpected and surprising result in view of the fact that compositions containing imidazolinium salts are known to have the opposite effect, i.e., impart soil retaining or scavenging properties to textiles, which properties improve in alcoholic solution. See US. Patent 3,105,500. This is further evidence of the unpredictability of result when known dispersants and other compounds are applied to fabrics such as carpets. The result is surprising also since, as demonstrated hereinafter, the use of anionic, nonionic and other cationic dispersants in combination with amides of Formula I, was unsuccessful and in some cases (cationics) produced an opposite effect, i.e., soil retention.
  • carpets and rugs When treated with the amides from alcoholic or alcohol-water dispersions according to the invention, carpets and rugs also exhibit water repel-lency and particularly resistance to soiling by beverages such as tomato juice, grape juice, cola and the like. This property is also observed when the treating compositions contain the imidazolinium salts, although to a lesser extent.
  • EXAMPLE 1 An aqueous ethanol solution (2:1 H 0:ethanol) containing 2% solids of N-(2,3-dihydroxypropyl)stearamide was applied by spraying to a 12" x 12" carpet sample consisting of 50% cut nylon pile and 50% burlap backing. Spraying was confined to the pile and the carpet sample increased 50% in Weight. Since the carpet increased in weight by 50% and contained 50% pile to which the spray was directed, it may be concluded that the pile actually increased in weight by and thus the pile contained compound solids equal to the concentration in the application bath, that is, 2%. The treated carpet was dried in an oven circulating hot air at 60 C. After drying, the carpet was vacuumed to remove loose pile and incidental dirt.
  • Soiling tests were then conducted by placing the treated carpet along with untreated carpets on the floor in a special ⁇ pattern.
  • the carpets were exposed to trafiic, e.g., dry soil, wet soil, tarry deposits, and the like.
  • the design of the samples was changed periodically according to a plan similar to that proposed by the American Association of Textile Chemists and Colorists (A.A.T.C.C.), American Dyestuif Reporter, May 13, 1963, pages 56-93. After each pattern change, the A.A.T.C.C. recommendations were followed to a predetermined level of soiling and included vacuuming.
  • soil index below 1.00 indicate soil retardancy; hence, the lower the value the more favorable is the soil retardancy.
  • Good soil retardants generally have soil indices below about 0.70. When a soil index value is greater than 1.00 it indicates that soil retention or scavenging is being effected.
  • the untreated control in a service soiling test is arbitrarily assigned a soil index of 1.00 and performance of other samples are calculated on such basis.
  • EXAMPLE 3 Aqueous alcohol solutions of different solids contents of N-(2,3-dihydroxypropyl)stearamide were applied to nylon carpet samples as in Example 1 so as to deposit 0.5, 1.0, 2.0, and 3.0% solids of N-(2,3-dihydroxypropyl) stearamide based on the weight of the carpet pile. Accelerated soiling tests as in Examples 1 and 2 were run on the treated samples. Results are given in Table III and show increasing soil retardancy with increasing applied solids.
  • EXAMPLE 4 Aqueous dispersions of the following compositions were applied to the same carpet type described in Example 1 using the same procedure as therein described.
  • the compositions contained N-(2,3-dihydroxypropyl)stearamide (NDHPSA) and various dispersants as follows wherein the numbers are parts by weight:
  • the carpet samples treated with compositions B, C and F were removed from the test pattern after five days because of heavy soiling and possibility of contamination of other samples by soil transfer.
  • the soil indices represent companative soiling of these samples relative to the untreated sample exposed to the full 16-day soiling test. These soil indices, in efiect, would be considerably greater if the samples were exposed for the full test duration or were compared to untreated carpets exposed for only five days.
  • Example 1 was repeated except that additional, separate applications were made to carpets of similar construction containing cut pile of the various types listed in Table V with results as shown therein. Testing was as in Example 1.
  • Table V -Service soiling of various carpets
  • the soil index values are relative to an untreated control carpet of same type having an assigned soil index of 1.00 and exposed to soiling at the same time.
  • compositions of the present invention are useful in imparting soil retardancy to carpets having pile of various fiber types.
  • EXAMPLE 6 Colloidal aqueous dispersions of alumina, silica, and titania were applied to nylon carpets according to the procedure of Example 1, except that the carpets were dyed in medium green shade.
  • NDHPSA N-(2,3-dihydroxypropyl)stearamide] was also applied to another sample of the same carpet material according to Example l.
  • a copolymer of sodium vinyl sulfonate and acrylamide was similarly applied to still another sample of the same material.
  • the pile of the carpet treated with the copolymer was very firm and rigid as a result of treatment and the pile of the carpets treated with the inorganic colloids was slightly firm.
  • the pile of the carpet treated with NDHPSA remained as soft and supple as untreated samples.
  • the carpets were subjected to soiling tests as in Example 1 except that visual ratings of the soilings were made instead of refiectances because of the color problem occasioned by the dye. All the carpet samples exhibited good soil retardancy after the few days of exposure. However, as exposure increased and as the samples were vacuumed, performance of the inorganic colloids and the copolymer became inferior to that of NDHPSA. After the full cycle of exposure to soiling and vacuuming, only the carpet treated with NDHPSA showed a clear advantage over the untreated carpet, i.e., a definitely cleaner, lighter shade, thus demonstrating the superiority of the treating agents of the present invention over known soil retardants.
  • a composition of matter effective for imparting soil retardance to textiles which consists essentially of an alco holic solution of an amide of the formula R-ii-NHCHQCHOHCHzOH wherein R is selected from the group consisting of alkyl, alkenyl and alkadienyl having from about 12 to 22 carbon atoms in an aqueous solution of one part of an imidazolinium compound of the formula wherein R is higher alkyl; R and R are each selected from the group consisting of hydroxyand polyhydroxysubstituted lower alkyl; and X is an anion.
  • composition of matter as in claim 1 wherein said amide is N-(2,3-dihydroxypropyl)coconutamide.
  • composition as in claim 1 wherein said amide is N-(2,3-dihydroxypropyl)stearamide.
  • composition as in claim 3 wherein said amide is N (2,3 dihydroxypropyl)stearamide and said imidazolinium compound is N-(2,3-dihydroxypropyl)-N-(2-hydroxyethyl)-2-heptadecylimidazolinium chloride.
  • composition as in claim 3 wherein said amide is N (2,3 dihydroxypropyl)stearamide and said imidazolinium compound is N-(2,3-dihydroxypropyl)-N-(2-hydroxyethyl)-2-heptadecyl-imidazolinium chloride.
  • a method of imparting soil retardancy to carpets which comprises applying thereto an effective amount of an amide of the formula wherein R is selected from the group consisting of alkyl, alkenyl and alkadienyl having from about 12 to 22 carbon atoms.
  • a method as in claim 8 wherein said amide is N-(2,3-dihydroxypropyl)stearamide.
  • a method of impartingsoil retardancy to carpets 8 which comprises applying an effective amount of an aqueous solution of an amide of the formula.
  • R is selected from the group consisting of alkyl, alkenyl and alkadienyl having from about 12 to 22 car'- bon atoms, said solution also containing a dispersant amount Within the range of one part for each 2 to 35 parts by weight of said amide of an imidazolinium compound of the formula an JJH.
  • R is higher alkylfR and R are each selected from the group consisting of hydroxyand polyhydroxysubstituted lower alkyl; and X is an anion.
  • Carpet fabric having thereon the dry residue of a solution in a volatile alcoholic solvent of an amide of the formulawherein R is selected from the group consisting of alkyl, alkenyl and'alkadienyl having from 12 to 22 carbon atoms, wherein the amount of said residue is effective to impart soil retardance to said carpet fabric.
  • carpet fabric as in claim 14 wherein said amide is N-(2,3-dihydroxypropyl)coconutamide.
  • carpet fabric having thereon the dry residue of an aqueous solution of an amide of the formula 0 I R-iIl-NHOHrOHOHCHzOH wherein R is selected from the group consisting of alkyl, alkenyl and alkadienyl having from about 12to 22 carbon atoms, said aqueous solution containing a dispersant amount within the range of one part for each 2 to 35 parts by weight ofsaid amide of an imidazolinium compound of the formula R1 N/ r L m 5 HzC- H2 wherein'R ,.:ishigher alkyl; R and R are each selected from the group consisting of hydroxyand polyhydroxysubstituted lower alkyl; and X- is an anion, wherein the amount of said residue is efiective to impart soil retardance to said carpet fabric.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US477575A 1965-08-05 1965-08-05 Soil retardant compositions and textile materials Expired - Lifetime US3424680A (en)

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GB (1) GB1117156A (enrdf_load_stackoverflow)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3644204A (en) * 1967-08-14 1972-02-22 Henkel & Cie Gmbh Agent for the post-treatment of washed laundry
US3753772A (en) * 1971-06-28 1973-08-21 Mill Master Onyx Corp Method and composition for providing antistatic and anti-soilant properties in hydrophobic fibers
US5223179A (en) * 1992-03-26 1993-06-29 The Procter & Gamble Company Cleaning compositions with glycerol amides
WO1995019415A1 (de) * 1994-01-12 1995-07-20 Henkel Kommanditgesellschaft Auf Aktien Tensidgemische mit verbesserten oberflächenaktiven eigenschaften

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2002613A (en) * 1932-02-29 1935-05-28 Gen Aniline Works Inc Reaction product of an organic acid amide and an alkylene oxide
US2876140A (en) * 1955-06-30 1959-03-03 Bibb Mfg Company Soil resistant textile material and method of making the same
US2957003A (en) * 1958-09-02 1960-10-18 Nalco Chemical Co Imidazolines and imidazolinium salts

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2002613A (en) * 1932-02-29 1935-05-28 Gen Aniline Works Inc Reaction product of an organic acid amide and an alkylene oxide
US2876140A (en) * 1955-06-30 1959-03-03 Bibb Mfg Company Soil resistant textile material and method of making the same
US2957003A (en) * 1958-09-02 1960-10-18 Nalco Chemical Co Imidazolines and imidazolinium salts

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3644204A (en) * 1967-08-14 1972-02-22 Henkel & Cie Gmbh Agent for the post-treatment of washed laundry
US3753772A (en) * 1971-06-28 1973-08-21 Mill Master Onyx Corp Method and composition for providing antistatic and anti-soilant properties in hydrophobic fibers
US5223179A (en) * 1992-03-26 1993-06-29 The Procter & Gamble Company Cleaning compositions with glycerol amides
CN1047616C (zh) * 1992-03-26 1999-12-22 普罗格特-甘布尔公司 含有丙三醇酰胺的洗涤组合物
CN1106445C (zh) * 1992-03-26 2003-04-23 普罗格特-甘布尔公司 含有丙三醇酰胺的洗涤组合物洗涤脏织物的方法
WO1995019415A1 (de) * 1994-01-12 1995-07-20 Henkel Kommanditgesellschaft Auf Aktien Tensidgemische mit verbesserten oberflächenaktiven eigenschaften
US5789372A (en) * 1994-01-12 1998-08-04 Henkel Kommanditgesellschaft Auf Aktien Surfactant mixtures having improved surface-active properties

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GB1117156A (en) 1968-06-19

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