US20020007517A1 - Cyclodextrin-based soft-hand compositions for textiles - Google Patents

Cyclodextrin-based soft-hand compositions for textiles Download PDF

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Publication number
US20020007517A1
US20020007517A1 US09/790,759 US79075901A US2002007517A1 US 20020007517 A1 US20020007517 A1 US 20020007517A1 US 79075901 A US79075901 A US 79075901A US 2002007517 A1 US2002007517 A1 US 2002007517A1
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United States
Prior art keywords
component
dispersion
weight
cyclodextrin
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US09/790,759
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English (en)
Inventor
Rolf Moors
Werner Stechele
Erich Rossler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Corp
Original Assignee
Individual
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
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Assigned to CIBA SPECIALTY CHEMICALS CORP. reassignment CIBA SPECIALTY CHEMICALS CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MOORS, DR. ROLF, ROSSLER, ERICH, STECHELE, WERNER
Publication of US20020007517A1 publication Critical patent/US20020007517A1/en
Abandoned legal-status Critical Current

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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
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03Polysaccharides or derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/65Mixtures of anionic with cationic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/22Carbohydrates or derivatives thereof
    • C11D3/222Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • 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
    • D06M13/10Treating 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 oxygen
    • D06M13/184Carboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/10Treating 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 oxygen
    • D06M13/184Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/188Monocarboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/463Compounds containing quaternary nitrogen atoms derived from monoamines
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/04Carboxylic acids or salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • 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
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50Modified hand or grip properties; Softening compositions

Definitions

  • This invention relates to aqueous dispersions that include a cyclodextrin, a carboxylic acid and a cationic surfactant. It further relates to the use of such dispersions for treating fiber materials, especially textile fabrics.
  • U.S. Pat. No. 5,234,611 describes fabric softeners that include polymer-encapsulated cyclodextrins. They are used for home laundry operations.
  • aqueous dispersion including at least the following components:
  • said components A to C accounting for 10 to 40% by weight of said dispersion and said dispersion including said components A, B and C in the following amount ratios relative to each other:
  • Dispersions according to the invention can be applied to the fiber materials by known methods, for example by padding.
  • the padding liquor is adjusted to a concentration customary in textile finishing and to the desired pH.
  • the aqueous dispersions of the invention, or the padding liquors may include further products as well as the abovementioned components A, B and C.
  • Such further products can be customary textile finishing ingredients such as flame retardants, polyolefins, and also silicones and fluoropolymers for oil and/or water repellency.
  • aqueous dispersions according to the invention may additionally include known cellulose crosslinkers such as dimethyloldihydroxyethyleneurea for example. This, following an appropriate, known thermal treatment of the fiber materials, will improve the durability of the effects obtainable with inventive dispersions on cellulose textiles.
  • cyclodextrins When dispersions according to the invention are used for textile treatment the known advantages of cyclodextrins are retained. These include, first, the ability to absorb perspiration or volatile gaseous products and so reduce odor nuisance. Secondly, cyclodextrins are known to be useful for including active ingredients such as scents in their voids and to rerelease them at a controlled rate in small doses. This makes it possible to impart a pleasant odor to textiles. For this purpose, the scent is combined with cyclodextrin according to known methods.
  • dispersions according to the invention provide a very pleasant soft hand and a controllable level of hydrophilicity.
  • Aqueous dispersions according to the invention may also be used with advantage for textile treatment in exhaust processes.
  • the hydrophilicity of the textiles can be controlled via the relative amounts of the components A, B and C or via the addition of nonionic dispersants, as described hereinbelow.
  • compositions according to the invention provide a distinct, synergistic effect with regard to the soft hand of textiles treated therewith.
  • the hand obtainable with compositions according to the invention is softer than the hand obtained with each one of the components A, B and C taken alone. Apart from that, it is difficult in many cases to prepare stable aqueous dispersions that contain only a component A and a component C, but not a component B.
  • Dispersions according to the invention include at least the three hereinbelow more particularly described components A, B and C. As mentioned, they may additionally include further ingredients.
  • Component A is an unsubstituted cyclodextrin or a mixture of such cyclodextrins.
  • Cyclodextrins are cyclic oligosaccharides made up of 6, 7 or 8 ⁇ -1,4-glycosidically linked D-glucopyranose units, in line with the definition in H. R. Christen et al., “Organische Chemie, Von denuben Kunststoffmaschine” , volume II, page 549, 1st edition 1990, Otto-Salle-Verlag, Frankfurt/M.
  • the compounds with 6, 7 and 8 units are termed respectively ⁇ -cyclodextrin, ⁇ -cyclodextrin and ⁇ -cyclodextrin.
  • Cyclodextrins are bacterial degradation products of starch. Particularly preferred dispersions according to the invention include at least ⁇ -cyclodextrin. They may additionally include ⁇ - and/or ⁇ -cyclodextrin. Cyclodextrins are commercial products, available for example from Wacker Chemie, Germany.
  • Component B is an aliphatic carboxylic acid of 8 to 24 carbon atoms or a mixture of such carboxylic acids. Linear or branched, saturated or unsaturated acids such as oleic acid can be used. Component B may further include monobasic or polybasic carboxylic acids. Component B preferably comprises saturated unbranched monobasic carboxylic acids (monocarboxylic acids) such as stearic acid or behenic acid. For cost reasons, component B normally comprises a mixture of technical grade carboxylic acids having a customary chain length distribution.
  • Component C is a cationic surfactant or a mixture of cationic surfactants.
  • Useful cationic surfactants include the surface-active compounds known from the technical literature.
  • Ammonium salts of inorganic or short-chain organic acids are very suitable for dispersions according to the invention. The cation of these salts may contain a quaternized nitrogen atom, but it is also possible for up to 3 hydrogen atoms to be attached to the nitrogen atom.
  • component C includes a surfactant of the general formula (I)
  • m is 0 or 1
  • n is from 1 to 8.
  • r is 0, 1 or 2
  • R 1 is an alkyl radical of 8 to 20 carbon atoms
  • R 2 and R 3 are independently hydrogen, an alkyl radical of 1 to 6 carbon atoms or a radical of the formula
  • X ⁇ is a monovalent anion of an inorganic or organic acid.
  • X ⁇ is the anion of monomethyl sulfate or the anion of a hydroxycarboxylic acid of 2 to 4 carbon atoms.
  • X ⁇ being an anion of the abovementioned kind.
  • Useful anions X ⁇ further include for example the anion of acetic acid, propionic acid, glycolic acid or lactic acid.
  • R 1 in the formula (I) is a linear or branched alkyl radical of 8 to 20 carbon atoms.
  • Alkyl R 2 or R 3 contains 1 to 6 carbon atoms and may be linear or branched.
  • Dispersions according to the invention include the components A, B and C in the following amount ratios relative to each other:
  • dispersions according to the invention can additionally include a nonionic surfactant or a mixture of such surfactants.
  • Particularly useful nonionic surfactants are ethoxylated carboxylic acids and ethoxylated alcohols. Silicones having polyoxyethylene groups or having amino groups in side chains can also be used, either alone or combined with the abovementioned nonionic surfactants.
  • the addition of these nonionic dispersants can additionally increase the hydrophilic properties of the textiles.
  • N-Methylol compounds known from the literature are useful for this purpose, but also so-called “formaldehyde-free” or “low-formaldehyde” crosslinkers.
  • Suitable cellulose crosslinkers are obtainable from Ciba Spezialitätenchemie Pfersee GmbH, for example products of the KNITTEX® range.
  • Application of such dispersions to fiber materials and drying is followed by a customary thermal treatment, for example at 160° C., to effect the crosslinking with the cellulose material. Following this treatment, the effects obtainable with dispersions according to the invention exhibit enhanced durability.
  • Aqueous dispersions according to the invention include 10 to 40% by weight of the sum total of components A, B and C. The remainder is either just water or water and other ingredients, for example of the abovementioned kind.
  • Such aqueous dispersions can be prepared according to commonly known methods, for example by initially charging water, adding the individual components in any order and homogenizing the mixture at 40° to 100° C. by mechanical agitation.
  • a mixture of the components A, B and C can be prepared without the use of water and stirred into water.
  • Aqueous dispersions according to the invention are particularly useful for treating non-made-up textile fabrics in the form of wovens or knits. This treatment accordingly preferably takes place on the premises of the textile finisher and not on the garment in the home.
  • the fiber materials which are preferably present as non-made-up wovens or knits can be further processed into articles of clothing. They may be comprised of natural fibers such as wool or cotton, of regenerated fibers such as viscose or synthetic fibers such as nylon or polyester or of blends of the fiber varieties mentioned.
  • An aqueous dispersion 1 was prepared by mixing together the hereinbelow specified components and homogenizing at about 80° C.:
  • Component f) modified polydimethylsiloxane having polyoxyethylene groups in side chains
  • Dispersions 1 and 2 had the compositions reported in the table which follows. TABLE Parts by Parts by Parts by Parts by Parts by Parts by Parts by weight of weight of weight of weight of weight of weight of weight of weight of Dispersion component a component b component c component d component e component f component g 1 2.2 6.2 5.3 3.2 0.7 0.4 82.0 2 2.2 0 5.3 3.2 0.7 0.4 82.0
  • Dispersions 1 and 2 which were both stable, were used to treat (pad) various wovens and knits composed of cotton, cotton/polyester, polyester and nylon, which were subsequently dried. The hand was then assessed, and the hydrophilicity of the textile fabrics was determined, by measuring the time for a drop of water to penetrate into the textile fabric.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US09/790,759 2000-02-26 2001-02-22 Cyclodextrin-based soft-hand compositions for textiles Abandoned US20020007517A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP00104047A EP1127940A1 (fr) 2000-02-26 2000-02-26 Adoucissant pour textiles à base de cyclodextrine
EP00104047.6 2000-02-26

Publications (1)

Publication Number Publication Date
US20020007517A1 true US20020007517A1 (en) 2002-01-24

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US09/790,759 Abandoned US20020007517A1 (en) 2000-02-26 2001-02-22 Cyclodextrin-based soft-hand compositions for textiles

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US (1) US20020007517A1 (fr)
EP (1) EP1127940A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060138380A1 (en) * 2003-06-26 2006-06-29 Torsten Kulke Aqueous liquid compositions of cyclodextrine or cyclodextrine derivatives and a process using the said composition
US7109324B1 (en) 2003-04-30 2006-09-19 Dan River, Inc. Process for chemically bonding an odor-encapsulating agent to textiles and textiles formed by the process
US20140178457A1 (en) * 2011-03-31 2014-06-26 GIANIS S.r.L. Binder and process for producing fabrics containing cyclodextrins fixed by said binder
US20170025023A1 (en) * 2014-04-08 2017-01-26 Technische Universität Dortmund Method for monitoring airspace
WO2017122162A1 (fr) * 2016-01-15 2017-07-20 Next Technology Tecnotessile Societa' Nazionale Di Ricerca R.L. Tissu fonctionnalisé

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7125833B2 (en) 2003-03-24 2006-10-24 Wacker Chemie Ag Cyclodextrin laundry detergent additive complexes and compositions containing same
DE102004035898B4 (de) * 2004-07-23 2008-04-24 Cht R. Beitlich Gmbh Textilausrüstungsmittel enthaltend einen Komplex aus gamma-Cyclodextrin und alpha-Tocopherol
DE102010023790A1 (de) 2010-06-15 2011-12-15 Heinrich-Heine-Universität Düsseldorf Waschaktive Zusammensetzung

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3478828B2 (ja) * 1992-11-16 2003-12-15 ザ、プロクター、エンド、ギャンブル、カンパニー 改善された布帛外観用染料移動抑制剤を有する布帛柔軟化組成物
US5470492A (en) * 1993-09-10 1995-11-28 The Procter & Gamble Company Dryer-activated fabric conditioning articles with soft polyester substrate
US6025321A (en) * 1996-03-29 2000-02-15 The Procter & Gamble Company Dryer-added fabric softener composition to provide color and other fabric benefits in package in association with instructions for use
ATE235544T1 (de) * 1996-10-30 2003-04-15 Procter & Gamble Gewebeweichmacherzusammensetzungen
US5905067A (en) * 1997-02-10 1999-05-18 Procter & Gamble Company System for delivering hydrophobic liquid bleach activators

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7109324B1 (en) 2003-04-30 2006-09-19 Dan River, Inc. Process for chemically bonding an odor-encapsulating agent to textiles and textiles formed by the process
US20060138380A1 (en) * 2003-06-26 2006-06-29 Torsten Kulke Aqueous liquid compositions of cyclodextrine or cyclodextrine derivatives and a process using the said composition
US20140178457A1 (en) * 2011-03-31 2014-06-26 GIANIS S.r.L. Binder and process for producing fabrics containing cyclodextrins fixed by said binder
US20170025023A1 (en) * 2014-04-08 2017-01-26 Technische Universität Dortmund Method for monitoring airspace
WO2017122162A1 (fr) * 2016-01-15 2017-07-20 Next Technology Tecnotessile Societa' Nazionale Di Ricerca R.L. Tissu fonctionnalisé

Also Published As

Publication number Publication date
EP1127940A1 (fr) 2001-08-29

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Owner name: CIBA SPECIALTY CHEMICALS CORP., NEW YORK

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:MOORS, DR. ROLF;STECHELE, WERNER;ROSSLER, ERICH;REEL/FRAME:011749/0380

Effective date: 20010110

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO PAY ISSUE FEE