WO1994025662A1 - Agents de resistance durable aux taches a base de polymeres d'acide methacrylique - Google Patents

Agents de resistance durable aux taches a base de polymeres d'acide methacrylique Download PDF

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Publication number
WO1994025662A1
WO1994025662A1 PCT/US1994/004059 US9404059W WO9425662A1 WO 1994025662 A1 WO1994025662 A1 WO 1994025662A1 US 9404059 W US9404059 W US 9404059W WO 9425662 A1 WO9425662 A1 WO 9425662A1
Authority
WO
WIPO (PCT)
Prior art keywords
methacrylic acid
resistance
stain
resist
acid
Prior art date
Application number
PCT/US1994/004059
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
Priority claimed from US08/051,824 external-priority patent/US5356689A/en
Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to AU67039/94A priority Critical patent/AU6703994A/en
Publication of WO1994025662A1 publication Critical patent/WO1994025662A1/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
    • D06M15/263—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
    • 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
    • D06M15/55—Epoxy resins

Definitions

  • compositions based on sulfonated phenol-formaldehyde condensates combined with polymers of methacrylic acid or hydrolyzed copolymers of maleic anhydride and ethylenically unsaturated compounds, when applied to polyamide substrates, will provide resistance to staining by acid dyes. While some improvement is also obtained in resistance to yellowing caused by UV and/or NOx and resistance to removal by commercial shampooing, it is far from optimum.
  • shampoo treatments typically utilize aqueous surfactant solutions with pH values of about 10. Such treatments remove part or all of the methacrylic acid polymer stain-resist agent.
  • the current invention provides a means to render such stain-resist agents less soluble by crosslinking the stain-resist agent so that the stain-resist properties of a stain-resist-treated polyamide substrate are retained to a greater extent after the treated substrate has been shampooed.
  • the present invention relates to novel compositions for imparting more durable stain-resistance to polyamide fiber substrates comprising blends of epoxy resins with methacrylic acid polymer stain- resists comprising either (I) copolymers containing more than 75 weight percent methacrylic acid or (II) polymers prepared by polymerizing methacrylic acid or mixtures of more than 75 weight percent methacrylic acid and less than 25 weight percent of one or more other ethylenically unsaturated monomers in the presence of a sulfonated phenol- formaldehyde condensation product.
  • This invention relates also to a process for imparting resistance to staining of polyamide substrates caused by acid dyes which consists essentially of (1) applying to said substrates (A) epoxy resins and (B) said methacrylic acid polymer stain-resists, and (2) heating the so-treated substrate to an elevated temperature sufficient to effect reaction between said epoxy resins and said methacrylic acid polymer stain-resists(thus, such elevated temperatures will be apparent to those skilled in the art from observation of such reactions).
  • the present invention relates also to the resulting polyamide substrates having said epoxy resins and said methacrylic acid polymer stain-resists reacted on them at said elevated temperatures.
  • Said methacrylic acid polymer stain-resist and said epoxy resin are usually applied at temperatures in the range between 20° and 60°C.
  • methacrylic acid polymer stain-resist % by weight of methacrylic acid polymer stain-resist, based on the weight of the polyamide substrate.
  • the amount of the epoxy resin needed to improve performance may range between 5 and 100 % of the weight of said methacrylic acid polymer stain-resist, preferably between 10 and 50 %.
  • the methacrylic acid polymer stain-resist agents of this invention show poor resistance to high pH values, particularly the pH of about 10 found in some commercial shampoo formulations. To be effective, the stain-resist agents should be applied at pH values below 4.0, preferably between 2.0 to 2.5.
  • the epoxy resins useful for the purposes of this invention are diverse in nature.
  • the water-dispersible epoxy resins useful for the purposes of this invention include any water-soluble or emulsifiable epoxy compounds containing two or more epoxy groups. Generally, these are resins of up to about 800 epoxy equivalent weight, preferably up to about 200, which may be saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or heterocyclic.
  • Such resins include epoxidized triglycerides, epoxy polyethers of polyhydric alcohols and phenols, glycidyl ethers of resins obtained by condensing an aldehyde with a polyhydric phenol, reaction products of polyhydric alcohols or phenols with a polyepoxide, polymers and copolymers of epoxy-containing monomers having at least one polymerizable ethylenic linkage, and epoxy esters of polybasic acids, including aliphatic diglycidyl ethers within the scope of Formula I below, such as ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, and trimethylene glycol diglycidyl ether.
  • x is a number having an average value of one to three
  • m is an integer having a value of two to four
  • x is a number having an average value of one to five.
  • All of these polyepoxides contain at least two vic-epoxy groups in which the epoxy oxygen atom is attached to adjacent carbon atoms and have molecular weights of about 160-1000.
  • the glycidyl ethers may preferably have molecular weights of about 180 to 400.
  • Other examples of epoxy resins are described in the article on epoxy resins, Kirk-Othmer, Encyclopedia of Chemical Technology, 2nd Edition, Vol. 8, pages 294-312, John Wiley and Sons, Inc. New York (1965).

Landscapes

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

Abstract

Composition destinée à conférer de la résistance aux taches laissées sur des substrats polyamides par des substances acides, qui résiste au shampoing et au jaunissement causé par l'exposition aux UV et/ou à Nox. Ladite composition comporte un mélange (A) d'une ou plusieurs résines époxy et (B) d'un agent polymère résistant aux taches qui contient (i) des copolymères comprenant plus de 75 pour cent en poids d'acide méthacrylique et moins de 25 pour cent en poids d'un ou plusieurs autres monomères éthyléniquement insaturés ou (ii) des polymères préparés par polymérisation (a) d'acide méthacrylique ou (b) de mélanges renfermant plus de 75 pour cent en poids d'acide méthacrylique et moins de 25 pour cent en poids d'un ou plusieurs autres monomères éthyléniquement insaturés en présence d'un produit de condensation de formaldéhyde hydroxyaromatique sulfoné.
PCT/US1994/004059 1993-04-26 1994-04-21 Agents de resistance durable aux taches a base de polymeres d'acide methacrylique WO1994025662A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU67039/94A AU6703994A (en) 1993-04-26 1994-04-21 Durable methacrylic acid polymer stain-resists

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US5182593A 1993-04-26 1993-04-26
US08/051,824 US5356689A (en) 1993-04-26 1993-04-26 Process providing durable stain-resistance using methacrylic acid polymers
US08/051,824 1993-04-26
US08/051,825 1993-04-26

Publications (1)

Publication Number Publication Date
WO1994025662A1 true WO1994025662A1 (fr) 1994-11-10

Family

ID=26729855

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/004059 WO1994025662A1 (fr) 1993-04-26 1994-04-21 Agents de resistance durable aux taches a base de polymeres d'acide methacrylique

Country Status (2)

Country Link
AU (1) AU6703994A (fr)
WO (1) WO1994025662A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996018765A1 (fr) * 1994-12-15 1996-06-20 Minnesota Mining And Manufacturing Company Composition resistant aux taches contenant un tensioactif sulfone
US5759431A (en) * 1994-12-15 1998-06-02 Minnesota Mining And Manufacturing Company Stain resistant composition containing sulphonated surfactant
WO2005093152A1 (fr) * 2004-03-24 2005-10-06 Invista Technologies S.A.R.L. Compositions resistant aux taches
US7344758B2 (en) 2004-09-07 2008-03-18 E.I. Du Pont De Nemours And Company Hydrocarbon extenders for surface effect compositions
US9481908B2 (en) 2007-04-04 2016-11-01 The Regents Of The University Of California Compositions, devices, systems, and methods for using a nanopore

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2739665A1 (de) * 1976-09-02 1978-03-09 Rohm & Haas Zubereitung fuer die behandlung von teppichen und teppichgarnen
US4388372A (en) * 1980-05-13 1983-06-14 E. I. Du Pont De Nemours And Company Durable antisoiling coatings for textile filaments
US4565717A (en) * 1983-10-20 1986-01-21 E. I. Dupont De Nemours And Company Antisoiling treatment of synthetic filaments
EP0332343A2 (fr) * 1988-03-11 1989-09-13 Minnesota Mining And Manufacturing Company Procédé pour rendre des matériaux polyamidiques résistants aux taches
US4940757A (en) * 1989-04-20 1990-07-10 Peach State Labs, Inc. Stain resistant polymeric composition
WO1990012917A1 (fr) * 1989-04-20 1990-11-01 Peach State Labs, Inc. Traitement antitaches pour fibres polyamides
WO1991019849A1 (fr) * 1990-06-12 1991-12-26 E.I. Du Pont De Nemours And Company Tissus resistant aux taches

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2739665A1 (de) * 1976-09-02 1978-03-09 Rohm & Haas Zubereitung fuer die behandlung von teppichen und teppichgarnen
US4388372A (en) * 1980-05-13 1983-06-14 E. I. Du Pont De Nemours And Company Durable antisoiling coatings for textile filaments
US4565717A (en) * 1983-10-20 1986-01-21 E. I. Dupont De Nemours And Company Antisoiling treatment of synthetic filaments
EP0332343A2 (fr) * 1988-03-11 1989-09-13 Minnesota Mining And Manufacturing Company Procédé pour rendre des matériaux polyamidiques résistants aux taches
US4940757A (en) * 1989-04-20 1990-07-10 Peach State Labs, Inc. Stain resistant polymeric composition
WO1990012917A1 (fr) * 1989-04-20 1990-11-01 Peach State Labs, Inc. Traitement antitaches pour fibres polyamides
WO1991019849A1 (fr) * 1990-06-12 1991-12-26 E.I. Du Pont De Nemours And Company Tissus resistant aux taches

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996018765A1 (fr) * 1994-12-15 1996-06-20 Minnesota Mining And Manufacturing Company Composition resistant aux taches contenant un tensioactif sulfone
US5759431A (en) * 1994-12-15 1998-06-02 Minnesota Mining And Manufacturing Company Stain resistant composition containing sulphonated surfactant
WO2005093152A1 (fr) * 2004-03-24 2005-10-06 Invista Technologies S.A.R.L. Compositions resistant aux taches
US7879112B2 (en) 2004-03-24 2011-02-01 Invista North America S.Ar.L. Stain-resist compositions
US7344758B2 (en) 2004-09-07 2008-03-18 E.I. Du Pont De Nemours And Company Hydrocarbon extenders for surface effect compositions
US9481908B2 (en) 2007-04-04 2016-11-01 The Regents Of The University Of California Compositions, devices, systems, and methods for using a nanopore

Also Published As

Publication number Publication date
AU6703994A (en) 1994-11-21

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