US3178309A - Treatment of wool and nylon to improve their resistance to abrasion - Google Patents

Treatment of wool and nylon to improve their resistance to abrasion Download PDF

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US3178309A
US3178309A US2978060A US3178309A US 3178309 A US3178309 A US 3178309A US 2978060 A US2978060 A US 2978060A US 3178309 A US3178309 A US 3178309A
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wool
water
nylon
weight
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Arthur J I Harding
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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
    • D06M15/53—Polyethers
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
    • 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
    • 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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/21—Nylon
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated 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
    • Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

United States Patent 3,178,309 TREATMENT 0F WOOL AND NYLDN TO M- PRGVE THEER RESISTANCE TG ABRASHON Arthur J. I. Harding, 1% S. Park Drive, Spartanburg, 55.6. No Drawing. Filed May 18, 1960, Ser. No. 29,780 7 Ciairns. (Cl. 117-1395) This invention relates to a process for treating wool and/ or nylon, and has as an object to improve the resistance of wool and/ or nylon fabrics to pilling.
According to the present invention a process is provided for treating wool and/or nylon with an aqueous liquid at a pH between 2 and 5, said liquid containing a condensation product of an aromatic sulphonic acid or a salt thereof and formaldehyde and a non-ionic dispersing agent or a water-repellent liquid polysiloxane at a temperature of between 150 F. and the boiling point of the liquid.
The process of the present invention may be applied to dyed or undyed material. In the case of undyed material the dyeing may, if desired, be effected during the process of the present invention or may be effected separately after the treatment.
The process of the present invention may be applied to yarns or knitted or woven fabrics or articles and is applicable to wool or nylon or mixtures of these mate rials, and also to yarns or fabrics or articles containing wool and/ or nylon in admixture with other fibers such as the synthetic protein fibers, e.g., material known under the name Ardil and the ethylene glycol terephthalic polyesters, e.g., material known under the name Terylene, cotton, rayon, casein, fiber, cellulose acetate, e.g., the viscose rayon material known under the name Fibre.
Among the articles which may be treated according to the present invention are underwear, or outerwear garments, hose, half-hose, quarter-hose, three-quarter hose, socks and stockings, felts, hats, ties, furnishing fabrics, upholstery for motor cars, gloves, scarves, wool curtains, rug and carpet Wool, rabbit wool and slubbing.
The fabrics or articles treated according to the process of the present invention show an increased resistance to pilling and likewise articles made from fibrous materials which have been treated according to the process of the present invention show an increased resistance to pilling.
The term pilling as used herein refers to the tendency of fabrics to form pills on the surface on rubbing. The tendency to pilling is measured by the well-known Martindale Tester which has a fixed plate and two plates moving eccentrically with respect to the fixed plate. The moving plates are each rotated by spindles and have a cushion of cloth or fabric to which the pieces of cloth under test are attached. Similarly two pieces of cloth are attached to the fixed plate. The test is conducted by rotating the moving plates and determining how many rubs are required to produce pilling.
The condensation products of aromatic sulphonic acids or salts thereof and formaldehyde may be formed from a Wide variety of aromatic sulphonic acids. Specific examples of these are dinaphthylmethane disulphonic acid, diphenylmethane disulphonic acid, dicresylmethane disulphonic acid, sodium dicresylmethane disulphonate, dixylylmethane disulphonic acid, diaminonaphthylmethane disulphonic acid, dichloronaphthylmethane disulphonic acid, dinitronaphthylmethane disulfonic acid, and dithiolnaphthylmethane disulphonic acid, each condensed with formaldehyde.
It will be understood that the condensation products may be made in situ and if desired a sulphite or bisulphite may be present during the condensation.
Examples of aromatic sulphonic acids containing at least three sulphonic acid groups and their water-soluble 3,1783% Patented Apr. 13, 1965 salts are: trisulphonic acids of aromatic hydrocarbons, including alkylated aromatic hydrocarbons, and watersoluble salts of such sulphonic acids, e.g., the sodium, potassium and ammonium salts such as the sodium salts of naphthalene trisulphonic acid, trisulphonic acid of monohydric, dihydric and trihydric phenols, including alkyl substituted phenols, and salts of such sulphonic acids. 7
It will be understood that mixtures of more than one of the above types of substance may be used, and it will be understood that the sulphonic acids of the aromatic hydrocarbons may contain more than one nucleus. Thus, for example, they may be derived from benzene, naphthalene, anthracene, diphenyl and dinaphthyl.
Substances which are of particular importance are condensation product of formaldehyde with mono, diand oi-sulphonic acids of aromatic hydrocarbons or phenols, especially diphenylmethane disulphonic acids, the condensation product of a cresol sulphonic acid with formaldehyde, or the condensation product of a naphthalene sulphonic acid with formladehyde, particularly dinaphthylmethane disulphonic acid.
The necessary pH value of the solution may be produced in any desired way but generally it will be convenient to add an appropriate amount of an acid such as acetic acid, hydrochloric acid, sulphuric acid, phosphoric acid or lactic acid.
Non-ionic dispersing agents are well known articles of commerce and examples of these are fatty alcohol-ethylene oxide condensates of the general formula where R is an alkyl group preferably containing more than eight carbon atoms and n is an integer greater than one, preferably greater than 20. Other examples are compounds of the general formulae where R and n have the meanings given above. Specific non-ionic dispersing agents are the materials sold under the names Dispersol VI. (a fatty alcohol-ethylene oxide condensate in water made by Imperial Chemical Industries, Ltd), Lubrol W (a fatty alcohol-ethylene oxide condensate made by Imperial Chemical Industries, Ltd.), Zelec DP and Zelec DX (higher polyethylene amine condensates made by E. I. du Pont de Nemours & Co.).
Water-repellent liquid polysiloxanes are well known articles of commerce and are generally lower alkyl, e.g., methyl, substances of the general formula:
a L Lia. L
where x is an integer greater than one or mixtures thereof (cf. Rob Roy McGregor, Silicones and Their Uses, 1st edition, p. 83).
After application the water-repellent liquid polysiloxanes may be caused to condensate further, preferably with the aid of a condensation catalyst.
Preferably the condensation product of an aromatic sulphonic acid or a salt thereof and formaldehyde is employed in the proportion of at least 0.5% by weight calculated on the weight of the goods being treated and preferably the non-ionic dispersing agent or the Water-repellent liquid polysiloxane is employed in a proportion of at least 1% calculated on the weight of the goods being treated.
The following examples illustrate the invention.
and
3 Example A bath was made up containing 870 ccs. of water, 0.87 gm. of 80% acetic acid, 2.9 gms. of Glaubers salt, 0.29 gm. of Irgasol DA (a condensation product of naphtha lene sulphonic acid and formaldehyde made by Geigy Chemical Co. Ltd.), 0.46 gm. of Drisil 105 and 0.12 gm. of Catalyst N21 (both made by Midlane Silicones, Ltd.). Drisil 105 is an oil-in-water type emulsion of a waterrepellent liquid polysiloxane containing 5% of perchloroethylene and 5% of toluene having a silicone content of 40% and a pH of 6 to 7, and a flash point of 73 to 90 F. Catalyst N21 is a curing catalyst recommended for use with Drisil 105. 0.058 gm. of acid yellow 61 (Xylene Fast Yellow P made by Sandoz Chemical Co. Ltd.), 0.058 gm. of acid violet 9 (Erio Fuchsine BBL made by Geigy Chemical Co. Ltd.) and 0.029 gm. of acid blue 59 (Coomassie Blue BL 200% made by Imperial Chemical Industries, Ltd.). 29 gms. of knitted wool fabric was entered into the bath of 100 F. The bath was brought to the boil and boiling continued until dyeing reached equilibrium. A blushsolid colour resulted. When tested in the Martindale Tester the material required, 35.6 rubs before pilling resulted, as compared with 21.3 rubs for the untreated material.
Example II Example I was repeated but using 0.58 gm. of Zelec DP instead of the Drisil 105 and Catalyst N21. The material required an average of 44.4 rubs before pilling resulted.
Example III A bath was made up containing 756 ccs. of water, 0.5 gm. of 60% acetic acid, 0.25 gm. of Irgasol DA, 2.5 gm. of Glaubers salt, 0.05 gm. of Xylene Fast Yellow P, 0.02 gm. of Erio Fuchsine BBL and 0.05 gm. of Coomassie Blue BL 200%. 25.5 grns. of wool fabric similar to that used in Example I was entered into the bath at 160 F. and maintained at this temperature for 20 minutes. Then the bath was raised to the boil and boiling continued until the dyestuffs were exhausted. The liquor was run away and 765 ccs. of water containing 0.5 gm. of Zelec DP at 120 F. was introduced and circulated through the fabric for 20 minutes at this temperature. The fabric was then rinsed. The material required an average of 41 3 b b fore pilling resulted.
Example IV Example I was repeated except that the Drisil 105 and the Catalyst N21 were replaced by 0.29 gm. of Zelec DP and the Irgasol DA was replaced by 0.29 gm. of naphthalene 1,5-di-sulphonic acid and 0.29 gm. of formaldehyde. The material required an average of 34.4 rubs before pilling resulted.
Example V A bath was made up containing 765 ccs. of water, 0.5 gm. of 80% acetic acid, 0.25 gm. of Irgasol DA, 2.5 gms. of Glaubers salt, 0.25 gm. of Zelec DX, 0.05 gm. of Xylene Fast Yellow P, 0.02 gm. of Erio Fuchsine BBL and 0.05 of Coomassie Blue BL 200%. 25.5 gms. of wool fabric similar to that used in Example I was entered into the bath at 160 F. and maintained at this temperature for 20 minutes. Then the bath was raised to the boil and boiling continued until the. dyestuffs were exhausted. The liquor was run away and 765 ccs. of water containing 0.75 gm. of Avitex FB, an exhausting agent, at 120 F. was introduced and circulated through the fabric for 20 minutes at this temperature. The fabric was then rinsed. The material required 35.0 rubs before pilling resulted. Avitex PE is a textile processing agent with slight ammoniacal odour, which serves to insolubilise the Zelec DX in a controlled manner so that the finish is deposited evenly on the material.
Example IV A bath was made up consisting 750 ccs. of water, 0.75
- perature for 30 minutes.
gm. of acetic acid, 0.38 gm. of Paralene 23344 (a condensation product of formaldehyde and naphthalene sulphonic acid and cresol sulfonic acid made by Yorkshire Dyeware & Chemical Co. Ltd.), 2.5 gms. of Glaubers salt and 0.5 gm. of Zelec DP. 25 gms. of dyed knitted wool fabric was entered at 160 F. and maintained at that tern- The material required an average of 40 rubs before pilling resulted as compared with 29.9 rubs for the untreated material.
Example VII Example VIII A bath was made up consisting of 750 ccs. of water, 0.75 gm. of 80% acetic acid, 2.5 gm. of Glaubers salt and 0.38 gm. of Irgasol DA. 25 gms. of material similar to that treated in Example VI was entered at 160 F. and then 0.5 gm. of Dispersol VL was added and the temperature maintained at 160 F. for 30 minutes. The material required an average of 54 rubs before pilling resulted.
Example IX A bath was made up consisting of 750 ccs. of water, 0.75 gm. of 80% acetic acid, 0.25 gm. of'Irgasol DA and 2.5 gms. of Glaubers salt. 25 gms. of scoured boys threequarter hose made of nylon plated on wool was entered at F. and the bath maintained at this temperature for 20 minutes. Then 0.25 gm. of Lubrol W was added and the temperature raised to F. and maintained for a further 20 minutes. The material required an average of 40 rubs before pilling resulted on the nylon as compared with 20 rubs for the untreated material.
What is claimed is:
1. A process comprising treating a textile material containing at least some fibers selected from the group consisting of nylon and wool and mixtures thereof with an aqueous liquid, at a pH of between 2 and 5, containing (1) at least 0.5% by weight, calculated on the weight of the textile material being treated, of a first compound selected from the group consisting of a water-soluble condensation product of an aromatic sulfonic acid and formaldehyde and a water-soluble salt of the condensation product, and (2) at least 1% by weight, calculated on the weight of the textile material being treated, of a nonionic dispersing agent, at a temperature between 150 F.
and the boiling point of the liquid.
2. The process of claim 1 wherein the pH of the aqueous liquid is provided by an appropriate amount of an acid selected from the groupconsisting of acetic, hydrochloric, sulfuric, phosphoric and latic acids.
3. The prcces of claim 1 wherein the first compound is a dinaphthylmethane disulphonic acid.
4. The proces of claim 1 where the non-ionic dispersing agent is a fatty alcohol-ethylene oxide condensate of the formula wherein R is an alkyl group containing more than eight carbon atoms and n is an integer greater than 20.
5. A process comprising treating a textile material containing at least some fibers selected from the group consisting of nylon and wool and mixtures thereof with an aqueous liquid, at a pH of between 2 and 5, containing (1) at least 0.5% by weight, calculated on the weight of the textile material being treated, of a first compound selected from the group consisting of a Water-soluble condensation product of an aromatic sulfonic acid and formaldehyde and a water-soluble salt of the condensation product, and (2) at least 1% by Weight, calculated on the weight of the textile material being treated, of a water-repellant liquid polysiloxane, at a temperature between 150 F. and the boiling point of the liquid.
6. The process of claim 5 wherein the first compound is a dinaphthylmethane disulphonic acid.
7. A proces of claim 5 wherein the pH of the aqueous liquid is provided by an appropriate amount of an acid selected from the group consisting of acetic, hydrochloric, sulfuric, phosphoric and lactic acids.
References Cited by the Examiner UNITED STATES PATENTS OTHER REFERENCES Ser. No. 391,542, Mueller et a1. (A.P.C.), published 10 A e1 27, 1943, abandoned.
Non-Ionic Surface Active Agents, Chemical Industries, March 1943, pp. 327-328.
RICHARD D. NEVIUS, Primary Examiner.

Claims (1)

1. A PROCESS COMPRISING TREATING A TEXTILE MATERIAL CONTAINING AT LEAST SOME FIBERS SELECTED FROM THE GROUP CONSISTING OF NYLON AND WOOL AND MIXTURES THEREOF WITH AN AUQEOUS LIQUID, AT A PH OF BETWEEN 2 AND 5, CONTAINING (1) AT LEAST 0.5% BY WEIGHT, CALCULATED ON THE WEIGHT OF THE TEXTILE MATERIAL BEING TREATED, OF A FIRST COMPOUND SELECTED FROM THE GROUP CONSISTING OF A WATER-SOLUBLE CONDENSATION PRODUCT OF AN AROMATIC SULFINIC-ACID AND FORMALDEHYDE AND A WATER-SOLUBLE SALT OF THE CONDENSATION PRODUCT, AND (2) AT LEAST 1% BY WEIGHT, CALCULATED ON THE WEIGHT OF THE TEXTILE MATERIAL BEING TREATED, OF A NONIONIC DISPERSING AGENT, AT A TEMPERATURE BETWEEN 150*F. AND THE BOILING POINT OF THE LIQUID.
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3343983A (en) * 1964-01-15 1967-09-26 Grace W R & Co Process of imparting shrink resistance to wool and the resulting product
US3427193A (en) * 1964-01-15 1969-02-11 Grace W R & Co Shrink resistant impregnated wool
US3628997A (en) * 1967-10-30 1971-12-21 Colgate Palmolive Co Method and means for treating fibrous materials and articles produced thereby
US3993439A (en) * 1970-07-03 1976-11-23 Hoechst Aktiengesellschaft Dispersing and stabilizing agents for dyestuffs
US4302202A (en) * 1979-10-09 1981-11-24 Northwestern Laboratories, Inc. Textile treating composition and method of use thereof
US4592940A (en) * 1983-12-16 1986-06-03 Monsanto Company Stain-resistant nylon carpets impregnated with condensation product of formaldehyde with mixture of diphenolsulfone and phenolsulfonic acid
US4619853A (en) * 1983-12-21 1986-10-28 Monsanto Company Easy-clean carpets which are stain resistant and water impervious
US4657555A (en) * 1984-02-02 1987-04-14 Fleissner Gmbh & Co., Maschinenfabrik Process for rendering wool sliver shrinkproof, and apparatus for performing the process
US4680212A (en) * 1986-03-06 1987-07-14 Monsanto Company Stain resistant nylon fibers
EP0235980A1 (en) * 1986-02-14 1987-09-09 E.I. Du Pont De Nemours And Company Textiles having stain resistance
EP0235989A1 (en) * 1986-02-14 1987-09-09 E.I. Du Pont De Nemours And Company Method for producing stain resistant polyamide fibers
US4800118A (en) * 1987-11-04 1989-01-24 West Point Pepperell Compositions and methods for imparting stain resistance to textile articles
US4839212A (en) * 1986-03-06 1989-06-13 Monsanto Company Stain resistant nylon carpets
US4879180A (en) * 1986-03-06 1989-11-07 Monsanto Company Stain-resistant nylon fibers
US5182154A (en) * 1983-12-16 1993-01-26 Monsanto Company Stain resistant nylon carpets

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1722904A (en) * 1928-01-18 1929-07-30 Rohm & Haas Condensed aromatic sulphonic acids and process of making same
US2199806A (en) * 1940-05-07 Wetting
US2826514A (en) * 1955-11-17 1958-03-11 Shell Dev Treatment of textile materials and composition therefor
US3010849A (en) * 1959-05-25 1961-11-28 Exxon Research Engineering Co Fabric conditioners

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2199806A (en) * 1940-05-07 Wetting
US1722904A (en) * 1928-01-18 1929-07-30 Rohm & Haas Condensed aromatic sulphonic acids and process of making same
US2826514A (en) * 1955-11-17 1958-03-11 Shell Dev Treatment of textile materials and composition therefor
US3010849A (en) * 1959-05-25 1961-11-28 Exxon Research Engineering Co Fabric conditioners

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3343983A (en) * 1964-01-15 1967-09-26 Grace W R & Co Process of imparting shrink resistance to wool and the resulting product
US3427193A (en) * 1964-01-15 1969-02-11 Grace W R & Co Shrink resistant impregnated wool
US3628997A (en) * 1967-10-30 1971-12-21 Colgate Palmolive Co Method and means for treating fibrous materials and articles produced thereby
US3993439A (en) * 1970-07-03 1976-11-23 Hoechst Aktiengesellschaft Dispersing and stabilizing agents for dyestuffs
US4302202A (en) * 1979-10-09 1981-11-24 Northwestern Laboratories, Inc. Textile treating composition and method of use thereof
US4592940A (en) * 1983-12-16 1986-06-03 Monsanto Company Stain-resistant nylon carpets impregnated with condensation product of formaldehyde with mixture of diphenolsulfone and phenolsulfonic acid
US5182154A (en) * 1983-12-16 1993-01-26 Monsanto Company Stain resistant nylon carpets
US4619853A (en) * 1983-12-21 1986-10-28 Monsanto Company Easy-clean carpets which are stain resistant and water impervious
US4657555A (en) * 1984-02-02 1987-04-14 Fleissner Gmbh & Co., Maschinenfabrik Process for rendering wool sliver shrinkproof, and apparatus for performing the process
EP0235989A1 (en) * 1986-02-14 1987-09-09 E.I. Du Pont De Nemours And Company Method for producing stain resistant polyamide fibers
EP0235980A1 (en) * 1986-02-14 1987-09-09 E.I. Du Pont De Nemours And Company Textiles having stain resistance
JPS62223378A (en) * 1986-02-14 1987-10-01 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー Production of antistaining polyamide fiber
AU588425B2 (en) * 1986-02-14 1989-09-14 E.I. Du Pont De Nemours And Company Method for producing stain resistant polyamide fibers
AU609384B2 (en) * 1986-02-14 1991-05-02 E.I. Du Pont De Nemours And Company Textiles having stain resistance
JP2595226B2 (en) 1986-02-14 1997-04-02 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー Method for reducing yellowing of polyamide fibers
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US4879180A (en) * 1986-03-06 1989-11-07 Monsanto Company Stain-resistant nylon fibers
USRE33365E (en) * 1986-03-06 1990-10-02 Monsanto Company Stain resistant nylon fibers
US4680212A (en) * 1986-03-06 1987-07-14 Monsanto Company Stain resistant nylon fibers
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