EP1325187B1 - Traitement de matieres textiles avec des polyorganosiloxanes - Google Patents

Traitement de matieres textiles avec des polyorganosiloxanes Download PDF

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Publication number
EP1325187B1
EP1325187B1 EP01976352A EP01976352A EP1325187B1 EP 1325187 B1 EP1325187 B1 EP 1325187B1 EP 01976352 A EP01976352 A EP 01976352A EP 01976352 A EP01976352 A EP 01976352A EP 1325187 B1 EP1325187 B1 EP 1325187B1
Authority
EP
European Patent Office
Prior art keywords
radical
radicals
textile material
formula
carbon atoms
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.)
Expired - Lifetime
Application number
EP01976352A
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German (de)
English (en)
French (fr)
Other versions
EP1325187A1 (fr
Inventor
Josette Chardon
Philippe Olier
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.)
Elkem Silicones France SAS
Original Assignee
Bluestar Silicones France SAS
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Filing date
Publication date
Application filed by Bluestar Silicones France SAS filed Critical Bluestar Silicones France SAS
Publication of EP1325187A1 publication Critical patent/EP1325187A1/fr
Application granted granted Critical
Publication of EP1325187B1 publication Critical patent/EP1325187B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • D06M15/19Treating 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
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • 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
    • D06M2200/25Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments
    • 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

  • the present invention relates to the utitisation of a composition for providing the textile fiber with good hydrophilicity, an absence of yellowing and a soft hand feel, that is to say softness properties.
  • the document US 4,409,267 describes for example the use of a mixed polyorganosiloxane carrying on the one hand primary (or secondary) amine function (s) substituted for example by residues containing an OH or O-group; alkyl, and secondly function (s) polyoxide (s) alkylene (s) as additive of a composition for the treatment of textile materials.
  • the document EP 546 231 discloses another approach via the use of a polyorganosiloxane bearing a unit (s) of formula Si - (CH 2 ) y - (OCH 2 ) y ' - CH (OH) CH 2 --N (CH 2 CH 2 OH) 2 where y is between 2 and 8 and y 'is 0 or 1.
  • EP 659 930 discloses silicone-based fabric softeners comprising from 2 to 1600 silicon atoms, carrying one to one hundred sterically hindered amine units and optionally other units such as, for example, alkyl radicals of 5 to 20 carbon atoms or radicals ( CH2) p-COO-R.
  • FR 2,745,825 discloses silicone fabric softeners carrying at least one sterically hindered amine unit and at least one polyether group of the formula (CH 2 ) n - (OCH 2 CH 2 ) ⁇ (OCH 2 CHCH 3 ) ⁇ - OR.
  • Another advantage of the use according to the present invention stems from the fact that it can be implemented with an industrially easy and storage stable polyorganosiloxane.
  • Another advantage of the use according to the present invention comes from the easy treatment of the composition containing the polyorganosiloxane according to the invention for its application to the materials to be treated.
  • the silicone oil used in the context of the invention does not require in particular the presence of other functions to provide hydrophilic properties to the treated textile material. However, if it is desired to obtain a hydrophilicity greater than that intrinsic to the material before treatment, the silicone oil used may contain other functions promoting this property.
  • the polyorganosiloxane of formula (I) used is linear.
  • the functional group V of the polyorganosiloxane of formula (I) used is chosen from the functional groups of formula (II).
  • the treatment process may be carried out on woven, non-woven or knitted form materials.
  • the fibers of these materials are at least partially hydrophilic, and this hydrophilicity is preserved after treatment with silicone according to the invention, notwithstanding the hydrophobic nature of its skeleton.
  • the at least partially hydrophilic materials may consist in particular of or based on cotton, linen, wool, viscose, rayon, hemp, silk or a mixture of these materials. These materials may be optionally mixed with other low or non-hydrophilic materials such as polyester (eg cotton-polyester blend), keratin, polypropylene, polyethylene, polyurethane, polyamide, cellulose acetate.
  • composition containing the polyorganosiloxane can be prepared in many forms: liquid, gaseous or solid.
  • a liquid preparation of the composition it will advantageously be aqueous in the form of solution, dispersion or emulsion.
  • the composition is prepared in the form of an aqueous emulsion.
  • the composition according to the process of the invention may also be used in solution in an organic solvent.
  • aqueous emulsions are generally based on a mixture of oil and water, and are prepared according to standard methods well known to those skilled in the art using surfactants.
  • the emulsions can be done by the so-called direct methods or by inversion. Their production is easy and does not require the use of equipment with high stirring speed. Normal speed stirring apparatus may be used.
  • the aqueous emulsions prepared according to the invention preferably contain between 20 and 90% by weight of water relative to the total mass of the constituents of the emulsion.
  • the emulsions prepared according to the invention are preferably diluted to contain between 95 and 99.5% by weight of water, relative to the total weight of the emulsion.
  • the application of the polyorganosiloxane according to the invention to the materials to be treated can be carried out in very different forms. Applications can be made by immersion, coating, spraying, printing, padding, or any other existing means.
  • the fabric when the fabric is treated with an aqueous composition containing a polyorganosiloxane according to the invention, said fabric is subjected to a heat treatment to quickly expel water in the form of steam.
  • the amount of polyorganosiloxane deposited on the material to be treated varies according to the constitution and manufacture of said material.
  • the applications of the compositions and in particular aqueous emulsions on the treated materials are carried out so that the increase in weight of the treated material does not exceed 0.1 to 20% by weight relative to the weight of the material before treatment.
  • the best results have been observed with a quantity of polyorganosiloxane of between 0.1 and 2% by weight relative to the weight of the material to be treated.
  • the previously defined polyorganosiloxanes may be prepared by different methods; for example: distribution or hydrosilylation.
  • oils are tested in application in the form of an aqueous emulsion and the measurements of hydrophilicity, non-yellowing and evaluation of the feel are carried out according to the tests described below.
  • the evaluation of the yellowing is carried out by measuring the color of the fabric (white cotton terry cloth at the beginning) after impregnation with the silicone oil and heat treatment for 9 minutes at 150 ° C.
  • the color measurement is made on a Sprectrophotocolorimeter ACS Sensor It sold by the company Datacolor.
  • the measurement conditions are the use of illuminant D65, reproducing daylight. From the measurement of the color of the tissue sample, the instrument calculates the values of different indices of white and yellow, among which we use the CIE white index.
  • the cotton terry cloth After applying the oil, the cotton terry cloth is dried in ambient air for 24 hours. After 1 minute heat treatment at 150 ° C, the fabric is placed 24 hours in conditioning (23 ⁇ 2 ° C, 50 ⁇ 5% relative humidity).
  • the polyester-cotton fabric (50/50) undergoes a heat treatment of 5 minutes at 170 ° C. It is then conditioned for 24 hours (23 ⁇ 2 ° C, 60 ⁇ 5% relative humidity).
  • the hydrophilicity measurements are given by the TEGEWA test in which the absorption time of a drop of water deposited on the surface of the fabric is measured. The shorter the time, the more the tissue is hydrophilic.
  • the silicone oils of the emulsions tested E1 to E7 have the following structure:
  • the emulsions are prepared using an inversion emulsification method, and have the following composition: 20 g of silicone oil tested, 8 g of surfactant (C 13 E 6 fatty alcohol), an amount of glacial acetic acid stoichiometrically necessary for the neutralization of the amine and the complement at 100 g with water.
  • 20 g of silicone oil tested 8 g of surfactant (C 13 E 6 fatty alcohol), an amount of glacial acetic acid stoichiometrically necessary for the neutralization of the amine and the complement at 100 g with water.
  • surfactant C 13 E 6 fatty alcohol
  • an amount of glacial acetic acid stoichiometrically necessary for the neutralization of the amine and the complement at 100 g with water.
  • the evaluations were carried out on textiles treated with 0.6% by weight of silicone oil.
  • the emulsions are applied to the fabric by padding.

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)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP01976352A 2000-10-05 2001-10-03 Traitement de matieres textiles avec des polyorganosiloxanes Expired - Lifetime EP1325187B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0012739 2000-10-05
FR0012739A FR2815049B1 (fr) 2000-10-05 2000-10-05 Procede pour adoucir, rendre hydrophile et non jaunissante une matiere textile, dans lequel on utilise une composition comprenant un polyorganosiloxane
PCT/FR2001/003046 WO2002029152A1 (fr) 2000-10-05 2001-10-03 Traitement de matieres textiles avec des polyorganosiloxanes

Publications (2)

Publication Number Publication Date
EP1325187A1 EP1325187A1 (fr) 2003-07-09
EP1325187B1 true EP1325187B1 (fr) 2008-11-26

Family

ID=8855041

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01976352A Expired - Lifetime EP1325187B1 (fr) 2000-10-05 2001-10-03 Traitement de matieres textiles avec des polyorganosiloxanes

Country Status (13)

Country Link
US (3) US20040083553A1 (zh)
EP (1) EP1325187B1 (zh)
CN (1) CN1210457C (zh)
AT (1) ATE415512T1 (zh)
AU (1) AU2001295652A1 (zh)
BR (1) BR0114523B1 (zh)
CA (1) CA2424832C (zh)
DE (1) DE60136729D1 (zh)
ES (1) ES2312473T3 (zh)
FR (1) FR2815049B1 (zh)
MX (1) MXPA03003004A (zh)
PT (1) PT1325187E (zh)
WO (1) WO2002029152A1 (zh)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2316346T3 (es) * 2000-10-27 2009-04-16 THE PROCTER & GAMBLE COMPANY Tratamiento para la ropa para conferir resistencia contra las arrugas en seco.
DE60309741T2 (de) 2002-12-03 2007-03-29 Unilever N.V. Behandlungszusammensetzungen für wäsche
FR2854175B1 (fr) * 2003-04-25 2006-01-06 Rhodia Chimie Sa Nouveau papier resistant a l'eau, repulpable, hydrophile et au toucher doux
US20040231815A1 (en) * 2003-04-25 2004-11-25 Rhodia Chimie Novel water-resistant, repulpable and hydrophilic paper having a soft feel
WO2008127519A1 (en) * 2007-04-11 2008-10-23 Dow Corning Corporation Silcone polyether block copolymers having organofunctional endblocking groups
WO2010047993A2 (en) 2008-10-22 2010-04-29 Dow Corning Corporation Aminofunctional endblocked silicone polyether copolymers in personal care compositions
CN107129574A (zh) * 2017-06-13 2017-09-05 江西晨光新材料有限公司 一种合成含哌啶基团氨基硅油的合成方法
CN109252375B (zh) * 2018-07-26 2022-06-03 广东雷邦高新材料有限公司 一种硅织物处理剂及其制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4927898A (en) * 1988-09-06 1990-05-22 Union Carbide Chemicals And Plastics Company Inc. Polysiloxanes with sterically hindered heterocyclic moiety
FR2642764B1 (fr) * 1989-02-03 1993-05-28 Rhone Poulenc Chimie Nouveaux composes a fonction piperidinyle et leur application dans la photostabilisation des polymeres
US5238731A (en) * 1991-05-10 1993-08-24 Allied-Signal Inc. Coemulsification of oxidized polyethylene homopolymers and amino functional silicone fluids
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.
US5540452A (en) * 1994-09-14 1996-07-30 Dana Corporation Gasket insert assembly
FR2729406B1 (fr) * 1995-01-16 1997-04-18 Rhone Poulenc Chimie Utilisation a titre d'antiadherent et/ou d'hydrofugeant de polyorganosiloxanes fonctionnalises, greffes
FR2757529B1 (fr) * 1996-12-24 1999-03-05 Rhodia Chimie Sa Compositions stables a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adherents
DE19729806A1 (de) * 1997-07-11 1999-03-18 Wacker Chemie Gmbh Wäßrige Organowasserstoffpolysiloxane enthaltende Emulsionen
US7336779B2 (en) * 2002-03-15 2008-02-26 Avaya Technology Corp. Topical dynamic chat

Also Published As

Publication number Publication date
US20080052839A1 (en) 2008-03-06
ATE415512T1 (de) 2008-12-15
FR2815049A1 (fr) 2002-04-12
US8038727B2 (en) 2011-10-18
ES2312473T3 (es) 2009-03-01
BR0114523B1 (pt) 2012-12-11
US20040083553A1 (en) 2004-05-06
PT1325187E (pt) 2009-01-20
CA2424832A1 (fr) 2002-04-11
WO2002029152A1 (fr) 2002-04-11
DE60136729D1 (de) 2009-01-08
CN1468336A (zh) 2004-01-14
CN1210457C (zh) 2005-07-13
CA2424832C (fr) 2007-05-29
US20060162093A1 (en) 2006-07-27
FR2815049B1 (fr) 2002-12-20
MXPA03003004A (es) 2003-07-14
BR0114523A (pt) 2003-08-26
EP1325187A1 (fr) 2003-07-09
AU2001295652A1 (en) 2002-04-15

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