WO2009065664A1 - Nouveaux composés de traitement de tissu - Google Patents

Nouveaux composés de traitement de tissu Download PDF

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Publication number
WO2009065664A1
WO2009065664A1 PCT/EP2008/063442 EP2008063442W WO2009065664A1 WO 2009065664 A1 WO2009065664 A1 WO 2009065664A1 EP 2008063442 W EP2008063442 W EP 2008063442W WO 2009065664 A1 WO2009065664 A1 WO 2009065664A1
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Prior art keywords
compound
group
poly
formula
hydrophobic
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PCT/EP2008/063442
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English (en)
Inventor
Ashish Anant Vaidya
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Unilever Plc
Unilever N.V.
Hindustan Unilever Limited
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Application filed by Unilever Plc, Unilever N.V., Hindustan Unilever Limited filed Critical Unilever Plc
Priority to MX2010005404A priority Critical patent/MX2010005404A/es
Priority to EP08805132A priority patent/EP2212374A1/fr
Priority to CN200880117329A priority patent/CN101868493A/zh
Publication of WO2009065664A1 publication Critical patent/WO2009065664A1/fr
Priority to ZA2010/02993A priority patent/ZA201002993B/en

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/392—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/395—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences

Definitions

  • the present invention relates to compounds having switchable surface properties and process for making such compounds.
  • Water and oil repellency generally means the ability of the fabric to block water and oil from penetrating into the fibers. Extensive efforts have been made to produce fabric surfaces having durable water and oil repellency, as well as improved and durable soil release characteristics. Some methods of treatment are available to impart either one of these properties to a fabric, but it has proven relatively difficult to provide all of these properties to fabrics, for any appreciable length of time. One method for treating fabrics to simultaneously impart both these characteristics utilises copolymers containing hydrophobic or oleophobic siloxane fluorocarbon based oil and water repellent segments, and hydrophilic soil release segments .
  • Natural fibers such as cotton and wool exhibit lower water and oil repellency, but when they do become soiled, they are readily cleaned, thus exhibiting easy soil release-ability.
  • synthetic fabrics notably polyester, exhibit lower level of soil release action during washing, but these fabrics do not get soiled as easily as cotton or wool. It is believed that the surface energy of cotton and other hydrophilic fabrics is high and therefore, cotton easily gets soiled by particulate stains, such as Carbon soot and dirt.
  • particulate stains such as Carbon soot and dirt.
  • the same high surface energy of cotton allows it to be cleaned with relative ease, as the stains are more easily released in water.
  • Synthetic fabrics like Polyester have low surface energies and therefore, their ability to attract particulate stains is much lower as compared to cotton. However, upon being stained, it becomes difficult to remove these stains from such fabrics, as their low surface energy prevents or retards the release of stains.
  • a fundamental physical property of any material is its surface energy. This property is usually expressed in mJ/m 2 . Depending on the magnitude of this property, materials may be classified as having high surface energy or low surface energy. This property generally depends on the composition of the substrate; for example, substrates having a surface that contains a significant portion of polar hydrophilic groups, such as hydroxyl, carboxylic acid, amino and the like, generally possess a high surface energy. Conversely, surfaces that contain a significant portion of non-polar hydrophobic groups such as silicone, fluorinated groups, and the like, generally exhibit lower surface energy.
  • porous or stainable surface such as fabric surface to exhibit high contact angles versus a variety of liquids, to prevent adsorption or staining. It would also be desirable for such surfaces to adapt to a change in their environment, such as in a cleaning or conditioning medium, to enhance removal of stains and soil.
  • Highly desirable would be a surface that reversibly adapts to its environment, such that the surface is stain resistant as well as easily cleanable and retains this ability through a number of use cycles.
  • US6899923 B2 (MILLIKEN & CO, 2005) describes a method of imparting durable repellency and stain release to a substrate in which the substrate is coated with a composition comprising of a hydrophilic stain release agent, a hydrophobic stain repellency agent, and a hydrophobic cross-linking agent, which is followed by heating the substrate to remove the excess liquid from the coated substrate; and optionally, further heating the coated substrate .
  • US6818253 B2 provides a method for treating substrates to obtain durable water repellency and improved durable soil release attributes, in which a mixture having a fluorocarbon polymer and a hydrophilic soil release polymer with ratio in the range of 1:1 and 5:1 and pH between 4 and 7 is applied to a fabric substrate, followed by drying. It is said that the hydrophilic soil release polymer is cationic in nature. It can be seen that the above methods are sequential and involve multiple stages, and therefore are cumbersome for use in everyday life; and more specifically, at the users' end.
  • the present inventors have found that for effective deposition on fabric surface, the compounds must have some organofunctional groups.
  • organofunctional groups During wash or rinse treatment, such compounds having switchable properties and containing organofunctional groups would deposit onto and also bind effectively with the fabric surface, thereby simultaneously allowing for co-existence of low and high surface energy segments for soil repellency and soil release benefits, respectively.
  • Such treated fabrics would exhibit low interfacial energies in both air (hydrophobic) and water (hydrophilic) environments, and therefore hold potential for minimizing adhesion and facilitating release of soils and stains from its surface in both air and water.
  • the present invention relates to compounds that exhibit auto-adaptable (switchable) surface energy properties and their use in treatment of fabrics.
  • Such surface energy properties provide relatively high advancing and receding contact angles for liquids when in contact with the fabric.
  • the fabric surface exhibits low surface energy of at most, about 20 mJ/m 2 , as measured by Goniometry and calculated by Fowkes equation, at a temperature of about 25 °C .
  • This unique ability for automatic surface energy modification provides surfaces those are both water and oil repellent, and which would exhibit high degree of stain resistance, and stain release in aqueous media.
  • this unique surface energy profile is repeatable and reversible, depending on the exposure environment.
  • Rl is a group selected from alkyl, branched alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, alkaryl, alkoxy, aryl, aralkyl, alkenyl, alkynyl or fluorocarbon groups containing 1 to 50 carbon atom(s), "X” is a hydrophilic polymer chain or segment, “Y” is a hydrophobic or oleophobic polymer chain or segment; “z” is a chain containing an organofunctional group which is an amide, quaternary ammonium, phosphate or sulfate group; R2 is same as Rl, or is Hydrogen, hydroxyl group or a spacer that links said compound of the formula (I) with another compound of the same formula; and a, b, c, d and e are integers from 1 to 4,000.
  • Rl is a is straight or branched alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, alkaryl, alkoxy, aryl, aralkyl, alkenyl, alkynyl or fluorocarbon group containing 1-50 carbon atoms (s) ;
  • r is an integer from 1 to 1000 and "s” is an integer from 4 to 16000, with all of the following:
  • R2 in said compound of the formula (I) when said R2 in said compound of the formula (I) is said spacer; a spacer compound selected from the group consisting of alpha, omega dienes; alpha, omega diynes; alpha, omega ene-ynes, or dialkenyl or dialkynyl terminated polymers selected from polysiloxanes or polyethers; said process being carried out in the presence of a catalyst, and optionally in the presence of an organic solvent or silicone fluid.
  • a method of treating fabric with a compound according to the principal aspect of the invention comprising a step of contacting the fabric with an aqueous dispersion of the compound.
  • the hydrophilic polymer chain or segment has poly (alkylene oxide), poly (propylene oxide), poly (vinyl alcohol), polysaccharide or poly (acrylic acid) units. More preferably, the hydrophilic polymer chain or segment contains poly (ethylene oxide) and poly (propylene oxide) units, as their surface energies are significantly high, generally in the range of 35 to 50 mJ/m2.
  • the hydrophobic or oleophobic polymer chain or segment contains perfluoropolyether, fluorocarbon, polystyrene or polymethylmethacrylate units.
  • Polymer chains containing fluorocarbon or perfluoropolyether residues are highly preferred as they offer substantially high degree of hydrophobicity and oleophobicity, owing to their extremely low surface energies, generally from 12 to 34 mJ/m 2 .
  • the organofunctional group is an amide, quaternary ammonium, phosphate or sulfate group. Further, it is preferred that all the groups are quaternary ammonium groups, as presence of these groups allows for enhanced deposition of the compound onto the fabric surface, in aqueous media.
  • each of the Rl groups in the compound of the formula (I) is a methyl, ethyl, propyl, butyl, or tertiary butyl group; and more preferably all are methyl groups.
  • the preferred range of each of a, b, c, d and e in the compound of the present invention is from 10 to 1000.
  • Silanic hydrogen (Si-H) containing silicone either linear or cyclic
  • base polymer either linear or cyclic
  • Rl is a is straight or branched alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, alkaryl, alkoxy, aryl, aralkyl, alkenyl, alkynyl or fluorocarbon group containing 1-50 carbon atoms (s) ; "r” is an integer from 1 to 4000 and “s” is an integer from 4 to 16000.
  • each of the Rl groups is a methyl, ethyl, propyl, butyl or tertiary butyl group. It is further preferred that all Rl groups are methyl groups.
  • silanic Hydrogens react with the respective reactive groups of the hydrophilic polymer, hydrophobic or oleophobic polymer, and the compound having an organofunctional group containing Nitrogen, Oxygen, Phosphorus or Sulphur. These reactants react with and bind covalently to the base polymer through the Si-H bond.
  • some Silanic Hydrogens react with the reactive sites of the spacer compound, which further reacts with another molecule of compound of the formula (I), because of the difunctional nature, to form 3-dimensional cross-linked structures.
  • the organofunctional group is an amide, quaternary ammonium, phosphate or sulfate groups. Preferred are quaternary ammonium groups. It is essential that the compounds having the above organofunctional groups also have a reactive group such as vinyl, allyl or propargyl; so that the compounds may react with the Silanic Hydrogens present on the Silicone backbone represented by (II) above followed by conversion into quaternary amino groups .
  • the base polymer chains are covalently linked to each other through the difunctional spacer groups.
  • These difunctional spacer groups prevent excessive three- dimensional crosslinking, and instead help in forming mildly crosslinked elastomeric compounds.
  • Preferred spacer compounds are selected from di alkenyl polyethers, alpha, omega dienes, alpha, omega diynes; alpha, omega ene- ynes or di alkenyl or dialkynyl terminated polysiloxanes .
  • Suitable examples of alpha, omega-dienes are 1, 4-pentadiene, 1,5- hexadiene, 1, 7-octadiene; 1, 8-nonadiene, 1, 9-decadiene,
  • alpha, omega-diynes 1, 3-butadiyne or 1, 5-hexadiyne, whereas alpha, omega ene-yne is preferably hexene-5-yne .
  • spacer groups are siloxane based.
  • Di-alkenyl terminated polysiloxanes, which are useful as spacer groups can be represented by the following general formula :
  • Rl is straight or branched alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, alkaryl, alkoxy, aryl, aralkyl, alkenyl, or alkynyl or fluorocarbon group containing 1 to 50 carbon atoms; where p is an average and is a number with a value in the range of 2-10000.
  • Preferred di-alkenyl terminated polyethers can be represented by the following general formulae:
  • n and m are integers from 1 to 10.
  • Suitable divalent moeties are selected from -(CH2)-; or -CH(Me)-; and the like.
  • a suitable addition catalyst are selected from metal complexes or their compounds or metals in free or immobilized form. Transition metals such as Platinum, Palladium and Rhodium are particularly preferred.
  • Preferred catalysts are Chloroplatinic acid, complexes of Platinum with unsaturated compounds e.g. Platinum (0) -1, 3- divinyl-1, 1, 3, 3-tetramethyldisiloxane complex; Platinum (0) - 2,4,6, 8-tetramethyl-2, 4, 6, 8-tetravinylcyclotetrasiloxane complex; PtO (1,5 cyclooctadine) i.e.
  • Pt(COD)] Platinum Phospine complexes; Platinum on Carbon; Platinum on inorganic supports such as silica and Platinum black.
  • Other metals such as palladium, rhodium complexes are also suitable for the reaction (for example Wilkinson's catalyst RhCl [ (C6H5) P] 3.
  • More Preferred catalysts are metal complexes or compounds or free metals or immobilized form of Transition metals such as Platinum, Palladium, Rhodium, Preferable catalysts are Chloroplatinic acid and complexes of platinum with unsaturated compounds.
  • the catalyst can be in heterogeneous phase, e.g., on charcoal or, preferably, in homogeneous phase (e.g. Karstedt catalyst). Platinum (0) - 1, 3-divinyl-l, 1, 3, 3-tetramethyldisiloxane complex was used most preferably.
  • the reaction between silanic hydrogen functional silicone base polymer and other reactants is optionally carried out in the presence of a solvent selected from water, a silicone fluid, polar organic compounds, non-polar organic compounds or mixtures thereof.
  • a solvent selected from water, a silicone fluid, polar organic compounds, non-polar organic compounds or mixtures thereof.
  • the solvent is present in an amount of 20 to 99.89 wt. % based on the weight of all reactants. More preferably the solvent is present in an amount of from 20 to 80 wt . % and still more preferably from 20 to 50 wt. %.
  • the solvent is a polar organic compound or non-polar organic compound, an amount should preferably be used to create a product containing ⁇ 40 wt . % solids.
  • the solvent is not removed from the composition.
  • Silicone fluids useful as the solvent include, but are not limited to alkyl and/or aryl siloxanes such as methyl siloxanes and alkyl and/or aryl siloxanes containing functional groups. Preferred are volatile methyl siloxanes (VMS) . VMS compounds correspond to the average unit formula (CH 3 ) D SiO ( 4 - D ) / 2 in which j has an average value of 2 to 3. The VMS compounds contain siloxane units joined by Si-O-Si bonds .
  • silicone fluids are polydimethylsiloxane, polydiethylsiloxane, polymethylethylsiloxane, polymethylphenylsiloxane, and polydiphenylsiloxane .
  • silicone fluids are used as the solvent herein, the resulting compound is in the form of silicone gels.
  • Polar organic compounds useful herein include monohydroxy alcohols such as ethyl alcohol and isopropyl alcohol; diols and triols such as propylene glycol, 2-methyl-1, 3-propane diol HOCH 2 CH(CH 3 )CH 2 OH, 1 , 2-hexanediol CH 3 (CH 2 ) 3 CH (OH) CH 2 OH, and glycerol; glycerol esters such as glyceryl triacetate (triacetin) , glyceryl tripropionate (tripropionin) , and glyceryl tributyrate (tributyrin) ; and polyglycols such as polyethylene glycols and polypropylene glycols, among which are Polypropylene glycol (PPG) 14 butyl ether C 4 H 9 [OCH (CH 3 ) CH 2 ] I 4 OH.
  • PPG Polypropylene glycol
  • PPG Polypropylene glycol
  • Non-polar organic compounds may also be used as the solvent.
  • the non-polar organic compounds include aromatic hydrocarbons, aliphatic hydrocarbons, alcohols, aldehydes, ketones, amines, esters, ethers, glycols, glycol ethers, alkyl halides, or aromatic halides.
  • Representative compounds are alcohols such as methanol, ethanol, 1-propanol, cyclohexanol, benzyl alcohol, 2- octanol, ethylene glycol, propylene glycol, and glycerol; aliphatic hydrocarbons such as pentane, cyclohexane, heptane, Varnish Maker's & Painter's (VM&P) solvent, and mineral spirits; alkyl halides such as chloroform, carbon tetrachloride, perchloroethylene, ethyl chloride, and chlorobenzene; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, and xylene; esters such as ethyl acetate, isopropyl acetate, ethyl acetoacetate, amyl acetate, isobutyl isobutyrate, benzyl acetate, and isopropyl palmitate
  • Suitable organic solvents are the ones that do not undergo a chemical reaction with any of the components of the silicone phase, under the anticipated conditions of processing and use and that is suitable for use in the intended end-use application .
  • the reaction temperature is in the range of 5°C to 200 0 C and preferably about 80 to 120 0 C and most preferably 110 0 C.
  • the reaction time may vary between 1 minute and 48 hours.
  • the compounds of the present invention are synthesized by a process comprising a step of reacting a compound having the general formula (II);
  • Rl is a is straight or branched alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, alkaryl, alkoxy, aryl, aralkyl, alkenyl, alkynyl or fluorocarbon group containing 1-50 carbon atoms (s) ;
  • r is an integer from 1 to 1000 and "s” is an integer from 4 to 16000, with all of the following:
  • R2 in said compound of the formula (I) when said R2 in said compound of the formula (I) is said spacer; a spacer compound selected from the group consisting of alpha, omega dienes; alpha, omega diynes; alpha, omega ene- ynes, or dialkenyl or dialkynyl terminated polymers selected from polysiloxanes or polyethers; said process being carried out in the presence of a catalyst, and optionally in the presence of an organic solvent or silicone fluid.
  • the compound was prepared by 3-stage reaction process
  • octamethycyclotetrasiloxane also known as D4
  • poly (methylhydro siloxane) CAS Number: 63148- 57-2, also known as MHPS
  • Tulsion catalyst which is an acidic catalyst (Thermax India, T63MP, sulfonic acid polystyrene resin) was added. The reaction mixture was stirred at 120 °C for 4 hours. Viscous compound of the formula (II) obtained was cooled down to room temperature.
  • CH2 CHCH2OCH2CH2 (CF2) nCF3 (Apollo Scientific, UK) ; were dissolved in 50 ml toluene (AR grade) and charged into a moisture-free reflux assembly, maintained under Nitrogen atmosphere. 25 ml of toluene was removed by azeotropic distillation to ensure complete removal of moisture content in the reaction medium. A drop of Platinum catalyst (Platinum (0) -1, 3-divinyltetramethyl-disiloxane complex solution (Available from Aldrich; CAS Number 68478- 92-2) was added to the reaction mixture and the mixture was stirred at room temperature for about 30 minutes.
  • Platinum catalyst Platinum (0) -1, 3-divinyltetramethyl-disiloxane complex solution (Available from Aldrich; CAS Number 68478- 92-2) was added to the reaction mixture and the mixture was stirred at room temperature for about 30 minutes.
  • R2 was same as Rl i.e. -CH3 (methyl) group.
  • a compound was prepared by following stages 1 and 2 (only) of Example-1. This resulted in a compound having epoxy functional group.
  • Divinyl terminated polysiloxane copolymer (VTP) copolymer obtained was cooled down to room temperature. Catalyst was filtered off. Un-reacted D4 was distilled off under vacuum at 125 °C . The product obtained was colorless, viscous oil. This was used as the spacer compound.
  • VTP Divinyl terminated polysiloxane
  • I g polyalkylene glycol monoallyl ether i.e. CH2 CHCH2-O- (EO) a- (PO)b-H (where EO is - (CH2CH2O) - and PO is - (CH2- CH(Me)-O)- a and b are each independently integers ranging from 1 to 20) (Polyglykol 20-10, Clariant) and 0.5 g "allyl, IH, lH,2H,2H-perfluorooctyl ether" i.e.
  • Platinum catalyst Platinum (0) -1, 3-divinyltetramethyl-disiloxane complex solution (Available from Aldrich; CAS Number 68478-92-2) was added to the reaction mixture and the mixture was stirred at room temperature for about 30 minutes.
  • the swatches were then dipped in distilled water, soaked for 15 minutes, removed from it and were allowed to dry in oven at 90 °C . Thereafter, the swatches were ironed.
  • a 12cm x 6cm strip of the treated fabric was cut and pasted on a smooth glass slide by applying adhesive to the corners of the fabric.
  • the slide was then placed on the platform of a Goniometer fitted with a camera.
  • a drop of water was placed on the fabric by using a syringe and photographed.
  • the contact angle of the drop of water in air on the fabric surface was determined. The change in contact angle with passage of time was recorded and the values have been reproduced in the table-1 below.
  • the experiment was performed in triplicate.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Silicon Polymers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

L'invention porte sur de nouveaux composés avec des propriétés de structure commutables : (formule 1) où R1 représente un groupe choisi parmi les groupes alkyles, alkyles ramifiés, cycloalkyles, polycycloalkyles, hétérocycloalkyles, alkaryles, alcoxy, aryles, aralkyles, alcényles, alcynyles ou fluorocarbonés, contenant 1 à 50 atomes de carbone, « X » est une chaîne ou un segment de polymère hydrophile, « Y » est une chaîne ou un segment de polymère hydrophobe ou oléophobe ; « z » est une chaîne contenant un groupe organofonctionnel qui est un groupe amide, ammonium quaternaire, phosphate ou sulfate ; R2 est identique à R1, ou représente Hydrogène, un groupe hydroxyle ou un groupe d'intercalation qui lie ledit composé représenté par la formule (I) avec un autre composé représenté par la même formule ; et a, b, c, d et e sont des entiers de 1 à 4 000. L'invention porte également sur un procédé de fabrication desdits composés, ainsi que sur un procédé de traitement de tissu par une dispersion aqueuse du nouveau composé.
PCT/EP2008/063442 2007-11-21 2008-10-08 Nouveaux composés de traitement de tissu WO2009065664A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
MX2010005404A MX2010005404A (es) 2007-11-21 2008-10-08 Novedosos compuestos para tratamiento de telas.
EP08805132A EP2212374A1 (fr) 2007-11-21 2008-10-08 Nouveaux composés de traitement de tissu
CN200880117329A CN101868493A (zh) 2007-11-21 2008-10-08 用于织物处理的新化合物
ZA2010/02993A ZA201002993B (en) 2007-11-21 2010-04-29 Novel compounds for fabric treatment

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US20120283381A1 (en) * 2011-05-04 2012-11-08 Ryuta Tamiya Macroinitiator containing hydrophobic segment
CN103306139A (zh) * 2013-07-10 2013-09-18 苏州市相城区开来化工有限公司 一种环保型氟硅防水剂
CN106832294B (zh) * 2017-01-21 2019-10-29 苏州逸微光电科技有限公司 一种新型氟硅聚合物以及表面处理剂

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RU2010125268A (ru) 2011-12-27
EP2212374A1 (fr) 2010-08-04

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