US20040083553A1 - Treating textile materials with polyorganosiloxanes - Google Patents
Treating textile materials with polyorganosiloxanes Download PDFInfo
- Publication number
- US20040083553A1 US20040083553A1 US10/381,912 US38191203A US2004083553A1 US 20040083553 A1 US20040083553 A1 US 20040083553A1 US 38191203 A US38191203 A US 38191203A US 2004083553 A1 US2004083553 A1 US 2004083553A1
- Authority
- US
- United States
- Prior art keywords
- radical
- radicals
- formula
- carbon atoms
- linear
- 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
Links
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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Definitions
- the present invention relates to a method for treating textile materials providing the textile fiber with good hydrophilicity, absence of yellowing and a soft feel to the touch, that is to say properties of softness.
- the document EP 546 231 describes another approach via the use of a polyorganosiloxane carrying a unit or units 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 equal to 0 or 1.
- EP 659 930 describes silicone-based textile softeners comprising from 2 to 1 600 silicon atoms, carrying one to one hundred sterically hindered amino units and optionally other units such as, for example, alkyl radicals having from 5 to 20 carbon atoms or radicals —(CH 2 ) p —COOR—R.
- FR 2,745,825 describes silicone-based textile softeners carrying at least one sterically hindered amino unit and at least one polyether type radical of formula (CH 2 ) n —(OCH 2 CH 2 ) ⁇ (OCH 2 CHCH 3 ) ⁇ —OR.
- Another advantage of the method of treating textile according to the present invention comes from the fact that it can be carried out with a polyorganosiloxane which is easy to prepare industrially and which is stable during storage.
- Another advantage of the method for treating textile 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.
- R 1 , R 2 and R 3 which are identical or different, represent a monovalent hydrocarbon radical chosen from linear or branched alkyl radicals having from 1 to 4 carbon atoms, linear or branched alkoxy radicals having from 1 to 4 carbon atoms, a phenyl radical and, preferably, a hydroxyl radical, an ethoxy radical, a methoxy radical or a methyl radical;
- R 4 is a divalent hydrocarbon radical chosen from:
- alkylene-carbonyl radicals in which the linear or branched alkylene portion contains 2 to 20 carbon atoms;
- alkylene-cyclohexylene radicals in which the linear or branched alkylene portion contains 2 to 12 carbon atoms and the cyclohexylene portion contains an OH group and optionally 1 or 2 alkyl radicals having 1 to 4 carbon atoms;
- U represents —O— or —NR 10 —, R 10 being a radical chosen from a hydrogen atom, a linear or branched alkyl radical containing 1 to 6 carbon atoms and a divalent radical of formula:
- R 4 has the meaning indicated above
- R 5 and R 6 have the meanings indicated below
- R 11 represents a linear or branched divalent alkylene radical having from 1 to 12 carbon atoms, one of the valency bonds (that of R 11 ) being linked to the atom of —NR 10 —, the other (that of R 4 ) being linked to a silicon atom;
- radicals R 5 which are identical or different, are chosen from linear or branched alkyl radicals having 1 to 3 carbon atoms and the phenyl radical;
- the radical R 6 represents a hydrogen radical or the radical R 5 or O..
- R′ 4 is chosen from a trivalent radical of formula:
- n represents a number from 2 to 20, and a trivalent radical of formula:
- U′ represents —O— or NR 12 —, with R 12 being a radical chosen from a hydrogen atom, a linear or branched alkyl radical containing 1 to 6 carbon atoms;
- R 5 and R 6 have the same meanings as those given with respect to the formula (II);
- the number of units ⁇ Si with a group V is between 1 and 5
- At least one of the silicone oils selected for the textile treatment is such that the number of units ⁇ Si with no group V is between 50 and 250, and the number of units ⁇ Si with a group V is between 1 and 3.
- the silicone oil used in the context of the invention in particular does not require the presence of other functional groups to provide the treated textile material with hydrophilic properties. However, if it is desired to obtain a hydrophilicity greater than that intrinsic to material before treatment, the silicone oil used may contain other functional groups which promote 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 method of treatment may be carried out on materials of the woven, nonwoven or knitted form.
- the fibers of these materials are at least partially hydrophilic, and this hydrophilicity is preserved after treatment with silicone according to the invention regardless of the hydrophobic nature of its backbone.
- the materials which are at least partially hydrophilic, may in particular consist of or be based on cotton, flax, wool, viscose, rayon, hemp, silk or a mixture of these materials. These materials may be optionally mixed with other materials which are scarcely or not hydrophilic, such as polyester (for example a cotton-polyester mixture), keratin, polypropylene, polyethylene, polyurethane, polyamide or cellulose acetate.
- composition containing the polyorgano-siloxane may be prepared in numerous forms: liquid, gaseous or solid.
- a liquid preparation of the composition it will be advantageously aqueous, either in the form of a solution, dispersion or emulsion.
- the composition is prepared in the form of an aqueous emulsion.
- the composition according to the method of the invention may also be used in solution in an organic solvent.
- the aqueous emulsions are generally based on a mixture of oil and water, and are prepared according to conventional methods well known to persons skilled in the art, using surfactants.
- the emulsions may be prepared by so-called direct methods or by inversion. Their implementation is easy and does not require the use of equipment having a high stirring rate. Equipment with a normal stirring rate may be used.
- the aqueous emulsions prepared in accordance with 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 in accordance with the invention are preferably diluted so as to contain between 95 and 99.5% by weight of water, relative to the total weight of the emulsion. These emulsions are found to be stable at room temperature.
- the application of the polyorganosiloxane according to the invention to the materials to be treated may be carried out in a wide variety of forms.
- the applications may be carried out by immersion, coating, spraying, impression, padding or by 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 in order to rapidly expel the water in vapor form.
- the quantity of polyorganosiloxane deposited on the material to be treated varies according to the make-up and the manufacture of said material.
- Applications of the compositions and in particular of aqueous emulsions to the treated materials are carried out such 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 were obtained with a quantity of polyorganosiloxane of between 0.1 and 2% by weight relative to the weight of the material to be treated.
- the polyorganosiloxanes defined above may be prepared according to various methods, for example: distribution or hydrosilylation.
- oils are tested by applying in the form of an aqueous emulsion and the measurements of hydrophilicity, nonyellowing and evaluation of feel are carried out according to the tests described below.
- the evaluation of the yellowing is carried out by measuring the color of the cloth (white cotton toweling at the beginning) after impregnation with silicone oil and heat treatment of 9 minutes at 150° C.
- the measurement of color is carried out on an ACS Sensor II spectrophotocolorimeter marketed by the company Datacolor.
- the conditions of measurement are the use of the D65 illuminant, which reproduces daylight.
- the apparatus uses the measurement of the color of the cloth sample, calculates the values of various whiteness and yellowing values, among which we shall use the CIE whiteness value.
- the cotton toweling After applying oil, the cotton toweling is dried in ambient air for 24 hours. After a heat treatment of 1 minute 30 seconds at 150° C., the cloth is placed for 24 hours for conditioning (23 ⁇ 2° C., 50 ⁇ 5% relative humidity).
- the polyester-cotton cloth (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 silicone oils of the emulsions tested E1 to E7 have the structure:
- the emulsions are prepared using a method of emulsification by inversion, and have the following composition: 20 g of silicone oil tested, 8 g of surfactant (C 13 E 6 fatty alcohol), a quantity of glacial acetic acid which is stoichiometrically necessary for neutralizing the amine and the balance for 100 g with water.
- surfactant C 13 E 6 fatty alcohol
- glacial acetic acid which is stoichiometrically necessary for neutralizing the amine and the balance for 100 g with water.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/391,531 US20060162093A1 (en) | 2000-10-05 | 2006-03-28 | Treating textile materials with polyorganosiloxanes |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
FR0012739 | 2000-10-05 | ||
PCT/FR2001/003046 WO2002029152A1 (fr) | 2000-10-05 | 2001-10-03 | Traitement de matieres textiles avec des polyorganosiloxanes |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/391,531 Continuation US20060162093A1 (en) | 2000-10-05 | 2006-03-28 | Treating textile materials with polyorganosiloxanes |
Publications (1)
Publication Number | Publication Date |
---|---|
US20040083553A1 true US20040083553A1 (en) | 2004-05-06 |
Family
ID=8855041
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/381,912 Abandoned US20040083553A1 (en) | 2000-10-05 | 2001-10-03 | Treating textile materials with polyorganosiloxanes |
US11/391,531 Abandoned US20060162093A1 (en) | 2000-10-05 | 2006-03-28 | Treating textile materials with polyorganosiloxanes |
US11/892,552 Expired - Fee Related US8038727B2 (en) | 2000-10-05 | 2007-08-23 | Treating textile materials with polyorganosiloxanes |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/391,531 Abandoned US20060162093A1 (en) | 2000-10-05 | 2006-03-28 | Treating textile materials with polyorganosiloxanes |
US11/892,552 Expired - Fee Related US8038727B2 (en) | 2000-10-05 | 2007-08-23 | Treating textile materials with 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) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040231815A1 (en) * | 2003-04-25 | 2004-11-25 | Rhodia Chimie | Novel water-resistant, repulpable and hydrophilic paper having a soft feel |
US20100048795A1 (en) * | 2007-04-11 | 2010-02-25 | John Kennan | Silicone polyether block copolymers having organofunctional endblocking groups |
US8734767B2 (en) | 2008-10-22 | 2014-05-27 | Dow Corning Corporation | Aminofunctional endblocked silicone polyether copolymers in personal care compositions |
Families Citing this family (5)
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. |
BR0316842A (pt) | 2002-12-03 | 2005-10-18 | Unilever Nv | Composição de tratamento na lavagem de roupas, método para a deposição de um silicone sobre um substrato, processo para a lavagem de tecidos à máquina ou à mão, e, uso de uma composição de tratamento na lavagem de roupas |
FR2854175B1 (fr) * | 2003-04-25 | 2006-01-06 | Rhodia Chimie Sa | Nouveau papier resistant a l'eau, repulpable, hydrophile et au toucher doux |
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)
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 |
-
2000
- 2000-10-05 FR FR0012739A patent/FR2815049B1/fr not_active Expired - Fee Related
-
2001
- 2001-10-03 ES ES01976352T patent/ES2312473T3/es not_active Expired - Lifetime
- 2001-10-03 EP EP01976352A patent/EP1325187B1/fr not_active Expired - Lifetime
- 2001-10-03 PT PT01976352T patent/PT1325187E/pt unknown
- 2001-10-03 CA CA002424832A patent/CA2424832C/fr not_active Expired - Fee Related
- 2001-10-03 US US10/381,912 patent/US20040083553A1/en not_active Abandoned
- 2001-10-03 BR BRPI0114523-1A patent/BR0114523B1/pt not_active IP Right Cessation
- 2001-10-03 CN CNB018169058A patent/CN1210457C/zh not_active Expired - Lifetime
- 2001-10-03 WO PCT/FR2001/003046 patent/WO2002029152A1/fr active Application Filing
- 2001-10-03 AU AU2001295652A patent/AU2001295652A1/en not_active Abandoned
- 2001-10-03 DE DE60136729T patent/DE60136729D1/de not_active Expired - Lifetime
- 2001-10-03 AT AT01976352T patent/ATE415512T1/de not_active IP Right Cessation
- 2001-10-03 MX MXPA03003004A patent/MXPA03003004A/es active IP Right Grant
-
2006
- 2006-03-28 US US11/391,531 patent/US20060162093A1/en not_active Abandoned
-
2007
- 2007-08-23 US US11/892,552 patent/US8038727B2/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040231815A1 (en) * | 2003-04-25 | 2004-11-25 | Rhodia Chimie | Novel water-resistant, repulpable and hydrophilic paper having a soft feel |
US20100048795A1 (en) * | 2007-04-11 | 2010-02-25 | John Kennan | Silicone polyether block copolymers having organofunctional endblocking groups |
US8013097B2 (en) | 2007-04-11 | 2011-09-06 | Dow Corning Corporation | Silicone polyether block copolymers having organofunctional endblocking groups |
US8734767B2 (en) | 2008-10-22 | 2014-05-27 | Dow Corning Corporation | Aminofunctional endblocked silicone polyether copolymers in personal care compositions |
Also Published As
Publication number | Publication date |
---|---|
WO2002029152A1 (fr) | 2002-04-11 |
US20080052839A1 (en) | 2008-03-06 |
CA2424832C (fr) | 2007-05-29 |
US8038727B2 (en) | 2011-10-18 |
BR0114523A (pt) | 2003-08-26 |
EP1325187A1 (fr) | 2003-07-09 |
PT1325187E (pt) | 2009-01-20 |
DE60136729D1 (de) | 2009-01-08 |
ATE415512T1 (de) | 2008-12-15 |
EP1325187B1 (fr) | 2008-11-26 |
FR2815049A1 (fr) | 2002-04-12 |
BR0114523B1 (pt) | 2012-12-11 |
MXPA03003004A (es) | 2003-07-14 |
CA2424832A1 (fr) | 2002-04-11 |
ES2312473T3 (es) | 2009-03-01 |
US20060162093A1 (en) | 2006-07-27 |
FR2815049B1 (fr) | 2002-12-20 |
AU2001295652A1 (en) | 2002-04-15 |
CN1210457C (zh) | 2005-07-13 |
CN1468336A (zh) | 2004-01-14 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: RHODIA CHIMIE, FRANCE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHARDON, JOSETTE;OLIER, PHILIPPE;REEL/FRAME:014206/0368 Effective date: 20030324 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |