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WO1993019238A1 - Revetements antitaches pour substrats de polyamide - Google Patents

Revetements antitaches pour substrats de polyamide Download PDF

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Publication number
WO1993019238A1
WO1993019238A1 PCT/US1993/002805 US9302805W WO9319238A1 WO 1993019238 A1 WO1993019238 A1 WO 1993019238A1 US 9302805 W US9302805 W US 9302805W WO 9319238 A1 WO9319238 A1 WO 9319238A1
Authority
WO
WIPO (PCT)
Prior art keywords
maleic anhydride
alpha
polymer
acid
substrate
Prior art date
Application number
PCT/US1993/002805
Other languages
English (en)
Inventor
Engelbert Pechhold
Original Assignee
E.I. Du Pont De Nemours And Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to DE69300635T priority Critical patent/DE69300635T2/de
Priority to EP93908582A priority patent/EP0632856B1/fr
Priority to AU39353/93A priority patent/AU664268B2/en
Priority to JP51683993A priority patent/JP3271766B2/ja
Priority to CA002132731A priority patent/CA2132731C/fr
Publication of WO1993019238A1 publication Critical patent/WO1993019238A1/fr

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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
    • D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • 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
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/34—Polyamides

Definitions

  • the present invention relates to polymeric stain-resist compositions.
  • Polyamide substrates such as nylon carpeting, upholstery fabric and the like, are subject to staining by a variety of agents, e.g., foods and beverages.
  • An especially troublesome staining agent is FD&C Red Dye No. 40, commonly found in soft drink preparations.
  • Different types of treatments have been proposed to deal with staining problems.
  • One approach is to apply a composition containing a sulfonated phenol-formaldehyde condensation product to the substrate.
  • sulfonated phenolformaldehyde condensation products are themselves subject to discoloration; commonly they turn yellow. Yellowing problems are described by W. H.
  • the present invention provides a composition useful for imparting stain resistance to a polyamide fibrous substrate comprising
  • a water-soluble or water-dispersible alpha-olefin/maleic anhydride polymer or a mixture of said polymers and (ii) a sulfonated phenol-formaldehyde condensation product, which is useful as a dye resist agent, a dye fixing agent, a dye reserving agent or an agent which improves the wet-fastness of dyeing on polyamide fibers.
  • compositions of the present invention show enhanced durability to shampoo washing of polyamide substrates treated with the compositions.
  • the invention provides stain resists which are more resistant to yellowing when exposed to UV light or NO x gases than are the sulfonated phenol/formaldehyde condensates.
  • At least some embodiments of the invention seek to provide a stain-resistant composition capable of imparting good stain resistance together with a low propensity to yellowing and having good substantive properties.
  • a further problem associated with prior art compositions is that they have low solubility in water at the low pH preferably used to treat textile articles unless surfactant is used.
  • At least some embodiments of the invention seek to provide a stain-resistant composition having a good water-solubility.
  • the Blend The two components may be blended together in a wide range of relative proportions.
  • the weight ratio of maleic anhydride copolymer to resin may lie in the range of between about 95:5 and 5:95, preferably between about 90:10 and about 10:90, more preferably between about 60:4040:60.
  • the pH of the blend is adjusted to the required pH preferably in the range about 1 to 3 more preferably 1.5 to 2.5 with acid.
  • the stain-resistant compostion of the present invention remains clear at such low pH. This finding is advantageous since the stain-resistant compostion of this invention need not contain any surfactant to solubilize the active ingredient. If desired however, the composition may contain a surfactant. Higher pH in the range up to about pH 7 to 9 may be used as well.
  • the maleic anhydride/alpha-olefin polymer The polymers useful for the purposes of this invention comprise one or more water-soluble or water-dispersible hydrolyzed maleic anhydride polymers.
  • alpha-olefins A variety of linear and branched chain alpha-olefins can be used for the purposes of this invention. Particularly useful alpha-olefins are dienes containing 4 to 18 carbon atoms, such as butadiene, chloroprene, isoprene, and 2- methyl-l,5-hexadiene; 1-alkenes containing 4 to 8 carbon atoms, such as isobutylene, 1-butene, 1-hexene, 1-octene, and the like, with isobutylene being most preferred.
  • alpha-olefins can be replaced by other monomers, e.g., up to 50 wt% of alkyl (C1.4) acrylates, alkyl (Ci .4) methacrylates, vinyl sulfides, N- vinyl pyrrolidone, acrylonitrile, acrylamide, as well as mixture of the same.
  • alkyl (C1.4) acrylates alkyl (Ci .4) methacrylates
  • vinyl sulfides e.g., N- vinyl pyrrolidone, acrylonitrile, acrylamide, as well as mixture of the same.
  • a part (preferably 1-75% by weight) of the maleic anhydride can be replaced by maleimide.
  • At least 95 wt% of the maleic anhydride co- or terpolymers have a number average molecular weight of in the range between about 700 and 200,000, preferably between about 1,000 and 100,000.
  • the maleic anhydride polymers useful in the present invention can be prepared according to methods well-known in the art.
  • the maleic anhydride polymers thus obtained can be hydrolyzed to the free acid or their salts by reaction with water or aqueous alkali, or they can also be reacted with C1.4 alkyl alcohol to provide polymeric alpha-olefin/maleic acid monoesters, which have stainblocking properties.
  • the polymers suitable for the purposes of this invention contain between about 0.7 and 1.3 polymer units derived from one ore more alpha-olefin monomers per polymer unit derived from maleic anhydride.
  • the alpha-olefin content of the polymers of this invention comprise between (a) 100 and 80 mol% of at least one 1-alkene contaimng 4 to 8 carbon atoms, or terminally unsaturated diene containing 4 to 18 carbon atoms, and (b) 0 to 20 mol% of at least one 1- alkene containing 3, or 10 to 18, carbon atoms.
  • Polymers containing about one polymer unit derived from one or more olefin monomers per polymer unit derived from maleic anhydride are most effective in imparting stain resistance to textile substrates.
  • the molecular weight of the polymers useful in the invention does not appear to be a limitation so long as the polymers are water-soluble or water- dispersible.
  • hydrolyzed isobutylene/maleic anhydride copolymer having number average molecular weights between about 6,000 and 100,000 impart good stain-resistance to polyamide substrates.
  • Even at a pH as low as 1.5 water-soluble isobutylene/maleic anhydride copolymers having number average molecular weights between about 6,000 and 100,000 remained in solution in water at 60°C.
  • the polymers suitable for the purposes of this invention can be prepared by hydrolyzing the maleic anhydride/olefin polymers according to methods well-known in the art. For example, they can be hydrolyzed to the free acid or their salts by reaction with water or alkali.
  • Suitable maleic anhydride polymers can conveniently obtained by hydrolysis of "Isobam”-01, an isobutylene maleic anhydride copolymer of molecular weight around 10,000, "Isobam”-04 a similar polymer having a molecular weight of around 40,000 or "Isobam”-10 a similar polymer having a molecular weight of around 100,000 with sodium hydroxide.
  • Other suitable maleic anhydride polymers include BM-30 available from Kuraray Co.
  • BM-30 is an isobutylene/maleic anhydride/N-phenylmaleimide terpolymer having a molecular weight of around 40,000.
  • a commercially available product usable without further treating is "Lindron” 10 (ex Lindau Chemical), a butadiene/maleic anhydride copolymer having a molecular weight of about 5,000 to 10,000.
  • Other suitable copolymers include monoesters of C4.8 alpha-olefin/maleic anhydride copolymers.
  • the monoesters can be obtained by a range of reactions well known to those skilled in the art.
  • a preferred method is by reaction with an alcohol by heating under reflux with the alcohol and then removing excess alcohol.
  • Preferred alcohols are C j .g alcohols especially methanol and ethanol.
  • the sulfonated phenol-formaldehyde resin which can be used for the purposes of this invention include any sulfonated hydroxy aromatic-formaldehyde condensation products which have been described in the prior art as being useful as dye-resist agents or dye-fixing agents, in other words, dye-reserving agents or agents which improve wetfastness or dyeings on polyamide fibers. See for example U.S. 4,592,940, U.S. 4,591,591, U.S. 3,790,344 and GB 1,291,784, the disclosure of which is specifically incorporated herein by reference.
  • condensation products suitable for the invention are MESITOL NBS, product of Bayer AG (a condensation product prepared from bis(4-hydroxyphenyl)-sulfone, formaldehyde, and phenol sulfonic acid; U.S. Patent No. 3,790,344), as well as ' ⁇ rional” NW, a product of Ciba-Geigy Corp., (formed by condensing a mixture of naphthalene monosulfonic acid, bis(hydroxyphenyl) sulfone and formaldehyde; U.S. Patent Number 3,716,393) and ' ⁇ rional" LY.
  • the sulfonated hydroxyaromatic formaldehyde products sold as "Stainfree" by Cybron Chemicals and "Algard” NS by Allied Colloid Co. are also suitable.
  • the stain-resistant composition can be effectively applied to polyamide fibrous substrates by a wide variety of methods known to those skilled in the art, such as: padding, spraying, foaming in conjunction with foaming agents, batch exhaust in beck dyeing equipment, or continuous exhaust during a continuous dyeing operation.
  • the stain-resist components of the present invention can be applied to the substrate separately or together as a blend.
  • stain- resistance of polyamide substrates is slightly better if the maleic anhydride/olefin polymer is applied to the polyamide substrate followed by the sulfonated phenol/formaldehyde condensate.
  • carpet mills in general prefer to apply components of a stain-resist mixture together, and such would be expected with the composition of this invention.
  • the stain resistant compositions of this invention can be applied by the foregoing methods to dyed or undyed polyamide textile substrates.
  • they can be applied to such substrates in the absence or presence of a polyfluoro- organic oil-, water-, and/or soil-repellent materials.
  • a polyfluoroorganic material can be applied to the textile substrate before or after application of the compositions of this invention thereto.
  • stain-resistant compositions are applied to the textile substrate at either 20°C followed by heat treatment at a temperature in the range between about 50 to 150°C for about 1 to 60 minutes, or applied at temperatures in the range between about 40 and 95°C for about 1 to 60 minutes.
  • a temperature between about 70 and 90°C is preferred.
  • stain-blocking can be obtained when application is effected even at that of cold tap water (10-15°C).
  • the stain-resistant compositions of this invention can also be applied in situ to polyamide ca eting which has already been installed in a dwelling place, office or other locale. They can be applied as a simple aqueous preparation or in the form of aqueous shampoo preparation, with or without one or more polyfluoro- organic oil-, water-, and/or soil- repellent materials. They may be applied at the levels described above, at temperature described, and at a pH between about 1 and 9, preferably between about 2 and 7.
  • a light blue dyed cut-pile carpet constructed from 70 oz/sq yd superba-set BCF nylon 66 is treated in a laboratory Beck apparatus for 20 minutes at 80°C (176°F) at a 20:1 liquor-to-goods ratio with a solution of a stain resist agent described in one of the examples of pH of 2.0 and in the presence of 2.0 g per liter of magnesium sulfate to give an application load of 0.8% owf. Based on active ingredients.
  • the carpet was then rinsed under tap water, partially de-watered by squeezing and dried in an forced-air oven for about 20 minutes at 121°C (250°F).
  • a commercially available latex composition (Textile Rubber Co. Calhoun, GA) was applied as to carpet backing adhesive, with a secondary polypropylene backing under the trade name Actionbac (AMOCO, Atlanta, GA).
  • a stain rating of 5 is excellent, showing outstanding stain resistance, whereas 1 is the worst rating comparable to an untreated control sample.
  • Shampoo Wash Durability Test A 3x5 inch carpet specimen was submerged for 5 minutes at room temperature in a detergent solution consisting of Duponol WAQE (1.5 g per liter) and adjusted with dilute sodium carbonate to a pH of 10 OJ. The specimen was then removed, rinsed thoroughly under tap water, de-watered by squeezing and air- dried. The dry carpet specimen was then tested according to the stain test described above.
  • UV Lightfastness Colorfastness to UV light was measured according to AATCC Test Method 16E-1987. The specimens were rated after exposure to 40 AATCC Fading
  • AFU Gray Scale Units
  • Example 2 To a solution of 259.7 of sodium hydroxide in 2073.6 g of dionized water at 60°C was slowly added under agitation 1,000 g of an isobutylene-maleic anhydride copolymer of molecular weight of about 40,000 and commercially available as "Isobam" -04 from Kuraray Corp., Japan. The reaction mass was agitated for 18 hours at 80-85°C. To this clear, amber liquid was then added at 60°C under stirring a solution of 683.3 g 30% sulfuric acid in 983.3 g deionized water to give a clear product having an active ingredient content of 20%, a viscosity of 606 Pa.s at a pH of 2.40.
  • Example 3 To a solution of 77.9 g of sodium hydroxide in 622.1 g deionized water at 40°C was slowly added 300 g of an isobutylene-maleic anhydride copolymer of 10,000 molecular weight, commercially available as "Isobam" -01 from Kuraray Corp., Japan. The exotherm during hydrolysis reached 70-90°C. The reaction mass was held for about 15 to 20 hours at 80-85°C.
  • Example 4 To 364.8 g of the polymer used in Example 3 was added under agitation at room temperature 50 g of a sulfonated hydroxyaromatic formaldehyde condensate available from Allied Colloid Co. as "Algard" NS (30% active ingredients) to give a clear brownish liquid having an active ingredient content of about 24.1%. This material remained clear at a pH of 2.0 at any desired concentration.
  • Example 5 To a solution of 26.0 g of sodium hydroxide in 207.4 g of deionized water was slowly added at 50°C under stirring 100 g of an isobutylene-maleic anhydride copolymer having a molecular weight of 10,000 and commercially available as "Isobam"-01 from Kuraray Co., Japan. A solution of 58.8 g of a sulfonated hydroxyaromatic formaldehyde condensate available from Bayer AG.

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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)
  • Detergent Compositions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyamides (AREA)

Abstract

L'invention se rapporte à un revêtement antitache pour textiles aux polyamides qui comprend des mélanges de polymères d'anhydride maléique/d'alpha-oléphines avec des produits de condensation au formaldéhyde-phénol sulfoné. Ces mélanges de revêtement antitache sont solubles dans l'eau à un pH faible, même en l'absence de tensioactif, et ils sont fortement substantifs et plus résistants au jaunissement que les produits de condensation.
PCT/US1993/002805 1992-03-25 1993-03-25 Revetements antitaches pour substrats de polyamide WO1993019238A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DE69300635T DE69300635T2 (de) 1992-03-25 1993-03-25 Fleckabweisende zusammensetzung fuer polyamidsubstrate.
EP93908582A EP0632856B1 (fr) 1992-03-25 1993-03-25 Revetements antitaches pour substrats de polyamide
AU39353/93A AU664268B2 (en) 1992-03-25 1993-03-25 Stain-resists for polyamide substrates
JP51683993A JP3271766B2 (ja) 1992-03-25 1993-03-25 ポリアミド基材用耐汚染剤
CA002132731A CA2132731C (fr) 1992-03-25 1993-03-25 Agent antitache pour substrats de polyamide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US85717992A 1992-03-25 1992-03-25
US85717892A 1992-03-25 1992-03-25
US07/857,179 1992-03-25
US07/857,178 1992-03-25

Publications (1)

Publication Number Publication Date
WO1993019238A1 true WO1993019238A1 (fr) 1993-09-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/002805 WO1993019238A1 (fr) 1992-03-25 1993-03-25 Revetements antitaches pour substrats de polyamide

Country Status (7)

Country Link
EP (1) EP0632856B1 (fr)
JP (1) JP3271766B2 (fr)
AU (1) AU664268B2 (fr)
CA (1) CA2132731C (fr)
DE (1) DE69300635T2 (fr)
MX (1) MX9301644A (fr)
WO (1) WO1993019238A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994018376A1 (fr) * 1993-02-02 1994-08-18 E.I. Du Pont De Nemours And Company Composition anti-tache a base de polymere anhydride maleique hydrolyse et durable
EP0758928A1 (fr) * 1995-02-13 1997-02-26 Shaw Industries, Inc. Procede de traitement de fil pour tapis et de tapis
WO1997011219A1 (fr) * 1995-09-22 1997-03-27 E.I. Du Pont De Nemours And Company Traitement de matieres en polyamide avec des fluoroesters ou des fluorothioesters partiels de polymeres d'acide maleique et des condensats aromatiques sulfones
WO1997028304A1 (fr) * 1996-01-31 1997-08-07 Minnesota Mining And Manufacturing Company Compositions et procedes pour rendre des articles resistants aux taches, et articles resistants aux taches
WO1998050619A1 (fr) * 1997-05-05 1998-11-12 Minnesota Mining And Manufacturing Company Traitement de substrats fibreux visant a leur conferer des proprietes hydrofuges, anti-taches et anti-salissures
WO1999057361A1 (fr) * 1998-04-30 1999-11-11 Minnesota Mining And Manufacturing Company Traitement de substrats fibreux pour conferer des proprietes a effet anti-mouillant, anti-tache et anti-salissure aux tapis
US6068805A (en) * 1999-01-11 2000-05-30 3M Innovative Properties Company Method for making a fiber containing a fluorochemical polymer melt additive and having a low melting, high solids spin finish
US6077468A (en) * 1999-01-11 2000-06-20 3M Innovative Properties Company Process of drawing fibers
US6117353A (en) * 1999-01-11 2000-09-12 3M Innovative Properties Company High solids spin finish composition comprising a hydrocarbon surfactant and a fluorochemical emulsion
US6120695A (en) * 1999-01-11 2000-09-19 3M Innovative Properties Company High solids, shelf-stable spin finish composition
US6207088B1 (en) 1999-01-11 2001-03-27 3M Innovative Properties Company Process of drawing fibers through the use of a spin finish composition having a hydrocarbon sufactant, a repellent fluorochemical, and a fluorochemical compatibilizer
US6537662B1 (en) 1999-01-11 2003-03-25 3M Innovative Properties Company Soil-resistant spin finish compositions
US7914890B2 (en) 2007-12-19 2011-03-29 E.I. Dupont De Nemours And Company Cyclic olefin-maleic acid copolymers for stain resists

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5436049A (en) * 1993-12-21 1995-07-25 Basf Corporation Process for the manufacture of a stain resistant carpet

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0306992A2 (fr) * 1987-09-11 1989-03-15 S.C. Johnson & Son, Inc. Polymères 1-alcène/anhydride maléique en excès
EP0329899A2 (fr) * 1987-12-21 1989-08-30 E.I. Du Pont De Nemours And Company Polymères aromatique/anhydride maléique résistant aux salissures
WO1991002116A1 (fr) * 1989-08-04 1991-02-21 E.I. Du Pont De Nemours And Company Procede d'application d'agents resistant aux taches
WO1992010605A1 (fr) * 1990-12-13 1992-06-25 E.I. Du Pont De Nemours And Company Agents anti-taches contenant des polymeres d'olefine/d'anhydride maleique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0306992A2 (fr) * 1987-09-11 1989-03-15 S.C. Johnson & Son, Inc. Polymères 1-alcène/anhydride maléique en excès
EP0329899A2 (fr) * 1987-12-21 1989-08-30 E.I. Du Pont De Nemours And Company Polymères aromatique/anhydride maléique résistant aux salissures
WO1991002116A1 (fr) * 1989-08-04 1991-02-21 E.I. Du Pont De Nemours And Company Procede d'application d'agents resistant aux taches
WO1992010605A1 (fr) * 1990-12-13 1992-06-25 E.I. Du Pont De Nemours And Company Agents anti-taches contenant des polymeres d'olefine/d'anhydride maleique

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994018376A1 (fr) * 1993-02-02 1994-08-18 E.I. Du Pont De Nemours And Company Composition anti-tache a base de polymere anhydride maleique hydrolyse et durable
EP0758928A4 (fr) * 1995-02-13 1998-12-02 Shaw Ind Inc Procede de traitement de fil pour tapis et de tapis
EP0758928A1 (fr) * 1995-02-13 1997-02-26 Shaw Industries, Inc. Procede de traitement de fil pour tapis et de tapis
WO1997011219A1 (fr) * 1995-09-22 1997-03-27 E.I. Du Pont De Nemours And Company Traitement de matieres en polyamide avec des fluoroesters ou des fluorothioesters partiels de polymeres d'acide maleique et des condensats aromatiques sulfones
US5750445A (en) * 1995-09-22 1998-05-12 E. I. Du Pont De Nemours And Company Treatment of polyamide materials with partial fluoroesters or fluorothioesters of maleic acid polymers and sulfonated aromatic condensates
WO1997028304A1 (fr) * 1996-01-31 1997-08-07 Minnesota Mining And Manufacturing Company Compositions et procedes pour rendre des articles resistants aux taches, et articles resistants aux taches
US6197378B1 (en) 1997-05-05 2001-03-06 3M Innovative Properties Company Treatment of fibrous substrates to impart repellency, stain resistance, and soil resistance
WO1998050619A1 (fr) * 1997-05-05 1998-11-12 Minnesota Mining And Manufacturing Company Traitement de substrats fibreux visant a leur conferer des proprietes hydrofuges, anti-taches et anti-salissures
WO1999057361A1 (fr) * 1998-04-30 1999-11-11 Minnesota Mining And Manufacturing Company Traitement de substrats fibreux pour conferer des proprietes a effet anti-mouillant, anti-tache et anti-salissure aux tapis
US6613862B2 (en) 1998-04-30 2003-09-02 3M Innovative Properties Company Treatment of fibrous substrates to impart repellency, stain resistance, and soil resistance
US6068805A (en) * 1999-01-11 2000-05-30 3M Innovative Properties Company Method for making a fiber containing a fluorochemical polymer melt additive and having a low melting, high solids spin finish
US6077468A (en) * 1999-01-11 2000-06-20 3M Innovative Properties Company Process of drawing fibers
US6117353A (en) * 1999-01-11 2000-09-12 3M Innovative Properties Company High solids spin finish composition comprising a hydrocarbon surfactant and a fluorochemical emulsion
US6120695A (en) * 1999-01-11 2000-09-19 3M Innovative Properties Company High solids, shelf-stable spin finish composition
US6207088B1 (en) 1999-01-11 2001-03-27 3M Innovative Properties Company Process of drawing fibers through the use of a spin finish composition having a hydrocarbon sufactant, a repellent fluorochemical, and a fluorochemical compatibilizer
US6468452B1 (en) 1999-01-11 2002-10-22 3M Innovative Properties Company Process of drawing fibers
US6536804B1 (en) 1999-01-11 2003-03-25 3M Innovative Properties Company High solids spin finish composition comprising a hydrocarbon surfactant and a fluorochemical emulsion
US6537662B1 (en) 1999-01-11 2003-03-25 3M Innovative Properties Company Soil-resistant spin finish compositions
US7914890B2 (en) 2007-12-19 2011-03-29 E.I. Dupont De Nemours And Company Cyclic olefin-maleic acid copolymers for stain resists

Also Published As

Publication number Publication date
DE69300635T2 (de) 1996-05-15
JPH07505450A (ja) 1995-06-15
MX9301644A (es) 1993-09-01
CA2132731A1 (fr) 1993-09-30
DE69300635D1 (de) 1995-11-16
AU3935393A (en) 1993-10-21
AU664268B2 (en) 1995-11-09
EP0632856A1 (fr) 1995-01-11
JP3271766B2 (ja) 2002-04-08
EP0632856B1 (fr) 1995-10-11
CA2132731C (fr) 2006-06-20

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