EP0546231B1 - Verfahren zur Weichmachung und Hydrophilierung von Textilmaterial mit einer ein Polyorganosiloxan enthaltenden Zusammensetzung - Google Patents

Verfahren zur Weichmachung und Hydrophilierung von Textilmaterial mit einer ein Polyorganosiloxan enthaltenden Zusammensetzung Download PDF

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Publication number
EP0546231B1
EP0546231B1 EP91403364A EP91403364A EP0546231B1 EP 0546231 B1 EP0546231 B1 EP 0546231B1 EP 91403364 A EP91403364 A EP 91403364A EP 91403364 A EP91403364 A EP 91403364A EP 0546231 B1 EP0546231 B1 EP 0546231B1
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Prior art keywords
radical
polydiorganosiloxane
composition
meq
polyorganosiloxane
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EP91403364A
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English (en)
French (fr)
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EP0546231A1 (de
Inventor
Edith Canivenc
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Rhodia Chimie SAS
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Rhone Poulenc Chimie SA
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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
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • 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
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/647Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2352Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2484Coating or impregnation is water absorbency-increasing or hydrophilicity-increasing or hydrophilicity-imparting

Definitions

  • the present invention relates to a process for packaging textile materials to give them a pleasant touch by hand, that is to say softness, at the same time as good hydrophilicity.
  • US-A-4 409 267 describes the use of a mixed polyorganosiloxane carrying a part of primary amine function (s) or of secondary or tertiary amine function (s) (s) substituted (s) for example by residues containing an OH or O-alkyl group, and on the other hand of alkylene polyoxide function (s) as additive of a composition for the treatment of textile materials.
  • GB-A-2 201 696 relates to a method for treating textile materials using a polyorganosiloxane carrying quaternary ammonium function (s) which does not have a substitution containing an OH or O-alkyl group.
  • EP-A-0 459 822 describes homogeneous and transparent detergent compositions comprising a polyorganosiloxane with secondary or tertiary amine function (s) substituted for example by residues containing an OH group, said group silicone being used in mixture with a softening agent based on a quaternary ammonium salt.
  • An advantage of the process according to the present invention is that it makes it possible to obtain textile materials having the two properties (softness and hydrophilicity) mentioned above.
  • Another advantage of the process according to the present invention is that it makes it possible to obtain textile materials exhibiting slight yellowing.
  • Another advantage of the process according to the present invention stems from the fact that it can be implemented with a polydiorganosiloxane of easy industrial preparation and stable in storage.
  • the polydiorganosiloxane used can optionally comprise monoorganosiloxy units RSi 1.5 and / or SiO2 units, but if they exist, these units are in the proportion of at most 2% relative to the number of diorganosiloxy units R2SiO, the meaning of R having been specified above.
  • the composition containing the polydiorganosiloxane defined above is an aqueous composition, in the form of an emulsion.
  • the nitrogen of the group X defined above can be salified, for example with an organic acid such as acetic acid.
  • R represents a C1 to C6 alkyl group.
  • polysiloxanes previously defined can be prepared in a similar manner to those described in American patent US Pat. No. 3,389,160, but using diethanolamine in place of dimethylamine.
  • the method according to the present invention can be implemented on any woven or knitted fabric and even on those made of nonwoven.
  • the fibers used for the production of these fabrics can be in particular cotton, polyester, polyamide, viscose, polyacrylate, wool, linen, cellulose acetate, as well as elastomeric fibers. It is of course possible to use mixtures of fibers.
  • this fabric is then subjected to a heat treatment in order to rapidly expel the water in the form of vapor.
  • an aqueous composition for example an emulsion
  • the amount of polysiloxane deposited on the treated fabric corresponds to an amount of between 0.1 and 1% by weight relative to the weight of the dry fabric treated.
  • the polyester yarn is coated (by a known technique) with a solution at 3% by weight of the polysiloxane with groups X previously defined in trichloroethane.
  • the coated wire is then dried continuously at 180 ° C. in a hot air oven at a speed of 200 m per minute (200 m / min).
  • a wire is thus obtained on which the deposit of polydiorganosiloxane product corresponds to 0.5% by weight relative to the weight of the dry wire.
  • the wire is then stored for 48 hours at 22 ° C, at 65% relative humidity.
  • the friction coefficient of the wire obtained is then determined on the ROTHSCHILD F device. Meter at the speed of 1 cm / min (centimeter per minute).
  • the test used to evaluate the hydrophilicity of the fabrics treated according to the method of the present invention is a test consisting in depositing a piece of treated fabric (25.4 x 25.4 mm) parallel to the surface of the distilled water located in a beaker and to measure the time between the deposition of this fabric on the water and the beginning of its descent into the water. This test is called "sinking test" in English.
  • the diethanolamine is condensed on an organosiloxane oil of average formula: measuring 36.6 meq / 100 g in glycidyl function.
  • a product is thus obtained whose average formula corresponds to the above product, but in which Z has been replaced by :-( CH2) 3-O-CH2-CH (OH) -CH2-N (C2H4OH) 2.
  • the emulsion is brought to pH 6 with acetic acid.
  • the products having the trade names TERGITOL TMN 10, TERGITOL TMN 6 and RENEX 30 are widely marketed surfactants known to those preparing emulsions.
  • TERGITOL TMN 6 comprises as active product a trimethylnonanol comprising 6 oxyethylene units.
  • TERGITOL TMN 10 comprises as active product a trimethylnonanol comprising 10 oxyethylene units.
  • RENEX 30 manufactured by ICI, comprises as active product a tridecylol comprising 10 oxyethylene units.
  • Example 3 the product prepared according to Example 3 is the one that best responds to the desired application, that is to say a soft feel and good hydrophilicity, when the fabric is cotton.

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)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (6)

  1. Verfahren zur Konditionierung von Textilmaterialien, um ihnen einen angenehmen Griff und eine gute Hydrophilie zu verleihen, bei dem die Textilmaterialien mit einer Zusammensetzung in Kontakt gebracht werden, die ein Polydiorganosiloxan als Träger von substituierter(n) Aminfunktion(en) umfaßt, gekennzeichnet durch die folgenden Punkte:
    · das verwendete Polydiorganosiloxan besitzt die allgemeine Formel
    Figure imgb0017
    in der
    - X ausgewählt wird unter den Resten
    Figure imgb0018
    · R' eine lineare oder verzweigte Alkylengruppe mit 2 bis 8 Kohlenstoffatomen darstellt,
    · R'' ein Wasserstoffatom oder eine Alkylgruppe mit 1 bis 6 Kohlenstoffatomen darstellt,
    · mit n zwischen 1 und 10, die abgrenzenden Werte eingeschlossen, und t gleich 0 oder 1,
    - die Reste R, gleich oder verschieden, unter dem Phenylrest, dem 3,3,3-Trifluorpropylrest und einem Alkylrest mit 1 bis 4 Kohlenstoffatomen ausgewählt werden,
    - Y einen Rest X oder einen Rest R darstellen kann,
    - p und q positive ganze Zahlen sind, und zwar solche, daß das verwendete Polyorganosiloxan im Mittel pro Molekül 50 bis 150 Siliciumatome und 2 bis 10 Gruppen X umfaßt;
    · 100 g des wie vorstehend definierten Polyorganosiloxans 25 bis 250 Milliäquivalent Aminstickstoff umfassen.
  2. Verfahren nach Anspruch 1, in dem
       n = 1 ist,
       R'' ein Wasserstoffatom bedeutet und
       t = 1 ist.
  3. Verfahren nach irgendeinem der vorstehenden Ansprüche, bei dem der Stickstoff der Gruppe X in Salz überführt ist.
  4. Verfahren nach irgendeinem der vorstehenden Ansprüche, bei dem die verwendete Zusammensetzung eine wäßrige Zusammensetzung ist.
  5. Verfahren nach irgendeinem der vorstehenden Ansprüche, bei dem die verwendete Zusammensetzung eine Emulsion ist.
  6. Verfahren nach irgendeinem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es auf einem Baumwollstoff durchgeführt wird.
EP91403364A 1990-12-06 1991-12-12 Verfahren zur Weichmachung und Hydrophilierung von Textilmaterial mit einer ein Polyorganosiloxan enthaltenden Zusammensetzung Expired - Lifetime EP0546231B1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9015525A FR2670221B1 (fr) 1990-12-06 1990-12-06 Procede pour adoucir et rendre hydrophile une matiere textile dans lequel on utilise une composition comprenant un polyorganosiloxane.

Publications (2)

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EP0546231A1 EP0546231A1 (de) 1993-06-16
EP0546231B1 true EP0546231B1 (de) 1995-08-23

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EP91403364A Expired - Lifetime EP0546231B1 (de) 1990-12-06 1991-12-12 Verfahren zur Weichmachung und Hydrophilierung von Textilmaterial mit einer ein Polyorganosiloxan enthaltenden Zusammensetzung

Country Status (12)

Country Link
US (1) US5277968A (de)
EP (1) EP0546231B1 (de)
JP (1) JPH04289276A (de)
AT (1) ATE126845T1 (de)
BR (1) BR9105281A (de)
CA (1) CA2057136A1 (de)
DE (1) DE69112408T2 (de)
DK (1) DK0546231T3 (de)
ES (1) ES2076494T3 (de)
FR (1) FR2670221B1 (de)
GR (1) GR3017752T3 (de)
IL (1) IL100246A (de)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2670221B1 (fr) * 1990-12-06 1994-05-13 Rhone Poulenc Chimie Procede pour adoucir et rendre hydrophile une matiere textile dans lequel on utilise une composition comprenant un polyorganosiloxane.
DE4222483A1 (de) * 1992-07-09 1994-01-13 Pfersee Chem Fab Organosiloxane mit Stickstoff enthaltenden und mit Äthergruppierungen enthaltenden Resten
FR2714402B1 (fr) * 1993-12-27 1996-02-02 Rhone Poulenc Chimie Procédé d'adoucissage textile non jaunissant dans lequel on utilise une composition comprenant un polyorganosiloxane.
US5563231A (en) * 1995-06-06 1996-10-08 Bayer Corporation Capped silanes and their application to textile substrates
FR2745825B1 (fr) * 1996-03-06 1998-04-17 Rhone Poulenc Chimie Procede pour adoucir et rendre non jaunissant et hydrophile une matiere textile dans lequel on utilise une composition comprenant un polyorganosiloxane
US6001140A (en) * 1996-04-04 1999-12-14 Witco Corporation Diesel fuel and lubricating oil antifoams and methods of use
TW354309B (en) * 1997-05-19 1999-03-11 Ind Technology And Res Inst Tertiary aminosiloxane polymer and process for preparing the same
US6140413A (en) * 1999-03-29 2000-10-31 Henkel Corporation Silicone softener viscosity reducer
DE60040853D1 (de) * 2000-10-27 2009-01-02 Procter & Gamble Behandlung von Geweben zur Erhöhung der Knitterfestigkeit in trockenem Zustand
US6642194B2 (en) 2001-11-07 2003-11-04 Chemsil Silicones, Inc. Clear conditioning detersive compositions and methods for making the same
US6605577B1 (en) 2001-11-07 2003-08-12 Chemsil Silicones, Inc. Clear conditioning detersive compositions containing polysiloxanes with at least one cyclic side chain
EP1561804B1 (de) * 2004-02-03 2008-08-13 The Procter & Gamble Company Feste Waschmittelzusammensetzung enthaltend Ton und Polydimethylsiloxan
ES2309461T3 (es) * 2004-02-03 2008-12-16 THE PROCTER & GAMBLE COMPANY Composicion para usar en el lavado o tratamiento de tejidos.
ES2340276T3 (es) * 2004-02-03 2010-06-01 THE PROCTER & GAMBLE COMPANY Composicion detergente para lavar la ropa, solida en particulas, que comprende arcilla y polidimetilsiloxano.
ATE393204T1 (de) * 2004-02-03 2008-05-15 Procter & Gamble Zusammensetzung zum waschen oder behandeln von wäsche
EP1561806B2 (de) * 2004-02-03 2018-04-04 The Procter & Gamble Company Zusammensetzung zur Wäschereinigung oder -behandlung, und ein Herstellungsverfahren für die Zusammensetzung
ATE423834T1 (de) * 2005-08-05 2009-03-15 Procter & Gamble Verfahren zur herstellung einer textilbehandlungshilfsmittelzusammensetzung und verfahren zur herstellung eines textilbehandlungs-und textilreinigungsmittels
EP1749879A1 (de) * 2005-08-05 2007-02-07 The Procter & Gamble Company Zusammensetzung zum Waschen oder Behandeln von Wäsche und Herstellungsverfahren
DE602005006796D1 (de) 2005-08-05 2008-06-26 Procter & Gamble Teilchenförmige Textilbehandlungsmittelzusammensetzung enthaltend Silikone, Schichtsilikate und anionische Tenside
EP2145944B1 (de) 2008-07-14 2014-03-26 The Procter & Gamble Company Partikel zur Vermittlung der stoffweichenden Abgabe auf damit behandelten Stoffen und zur Bereitstellung einer gewünschten Schaumunterdrückung
EP2559806A1 (de) 2011-08-17 2013-02-20 Center of Excellence Polymer Materials and Technologies (Polimat) Verfahren zum Steigern der Hydrophilie polymerer Materialien

Family Cites Families (8)

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JPS5934820B2 (ja) * 1980-07-07 1984-08-24 ト−レ・シリコ−ン株式会社 繊維用処理剤
JPS6036513B2 (ja) * 1981-02-05 1985-08-21 ト−レ・シリコ−ン株式会社 繊維用処理剤
JPS57171768A (en) * 1981-04-15 1982-10-22 Shinetsu Chem Ind Co Fiber treating agent
GB8704001D0 (en) * 1987-02-20 1987-03-25 Unilever Plc Conditioning fabrics & compositions
FR2648821A1 (de) * 1989-06-22 1990-12-28 Rhone Poulenc Chimie
US5000861A (en) * 1989-08-23 1991-03-19 Union Carbide Chemicals And Plastics Co. Inc. Stable emulsions containing amino polysiloxanes and silanes for treating fibers and fabrics
AU641014B2 (en) * 1990-06-01 1993-09-09 Unilever Plc Liquid fabric conditioner and dryer sheet fabric conditioner containing compatible silicones
FR2670221B1 (fr) * 1990-12-06 1994-05-13 Rhone Poulenc Chimie Procede pour adoucir et rendre hydrophile une matiere textile dans lequel on utilise une composition comprenant un polyorganosiloxane.

Also Published As

Publication number Publication date
DE69112408D1 (de) 1995-09-28
EP0546231A1 (de) 1993-06-16
IL100246A0 (en) 1992-09-06
JPH04289276A (ja) 1992-10-14
GR3017752T3 (en) 1996-01-31
ATE126845T1 (de) 1995-09-15
FR2670221B1 (fr) 1994-05-13
BR9105281A (pt) 1992-08-18
FR2670221A1 (fr) 1992-06-12
DE69112408T2 (de) 1996-03-07
CA2057136A1 (fr) 1992-06-07
ES2076494T3 (es) 1995-11-01
US5277968A (en) 1994-01-11
IL100246A (en) 1994-10-21
DK0546231T3 (da) 1996-01-08

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