WO2002006580A1 - Composition de traitement de tissus et procede de traitement de tissus et composants amphiphiles perfluoroalkyles - Google Patents

Composition de traitement de tissus et procede de traitement de tissus et composants amphiphiles perfluoroalkyles Download PDF

Info

Publication number
WO2002006580A1
WO2002006580A1 PCT/EP2001/006376 EP0106376W WO0206580A1 WO 2002006580 A1 WO2002006580 A1 WO 2002006580A1 EP 0106376 W EP0106376 W EP 0106376W WO 0206580 A1 WO0206580 A1 WO 0206580A1
Authority
WO
WIPO (PCT)
Prior art keywords
fabric
perfluoroalkyl
general formula
alkyl
group
Prior art date
Application number
PCT/EP2001/006376
Other languages
English (en)
Inventor
Jun Huang
De-Bao Su
Shang-Ren Wu
Original Assignee
Unilever Plc
Unilever Nv
Hindustan Lever Limited
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
Application filed by Unilever Plc, Unilever Nv, Hindustan Lever Limited filed Critical Unilever Plc
Priority to AU2001279644A priority Critical patent/AU2001279644A1/en
Publication of WO2002006580A1 publication Critical patent/WO2002006580A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/004—Surface-active compounds containing F
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating 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
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/408—Acylated amines containing fluorine atoms; Amides of perfluoro carboxylic acids
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/32—Polyesters
    • 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
    • D06M2200/10—Repellency against liquids
    • D06M2200/11—Oleophobic properties
    • 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
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties

Definitions

  • the present invention relates to a fabric treatment composition comprising a perfluoroal yl amphiphilic compound.
  • the present invention also relates to a method of treating fabric using a perfluoroalkyl amphiphilic compound.
  • the present invention further provides a novel class of perfluoroalkyl amphiphilic compounds.
  • the present invention further provides a method of synthesising perfluoroalkyl amphiphilic compounds for use in fabric treatment.
  • the present invention is concerned with fabric treatment.
  • the fabric treatment may be treatment before use, for example during the manufacture of fabric or garments, or it may take place after use of the fabric.
  • Fabric treatment that takes place after use of the fabric here termed fabric care, is used to reverse degradation of fabric that occurs as a result of use of the fabric, for example soiling and staining.
  • Such treatments include laundering and the application of non-laundry fabric care products, such as spray-on products.
  • EP-A-0240601 discloses perfluoroalkyl polyglycerine compounds of general formula A:
  • R f is a perfluoro alkyl moiety
  • Q is a divalent linking group
  • K is 0 or 1
  • A is an alkenylene or divalent aryl linking group and p is 1-15.
  • compositions can be used to give oil and soil repellency to textiles, leather, wood or paper.
  • Compounds of formula A are amphiphilic - the polyglycerine chain has hydrophilic properties whereas the perfluoroalkyl moiety has hydrophobic properties.
  • Compounds of general formula A include an ether group between the polyglycerine chain and the rest of the molecule. Such ether bonds can be difficult to synthesise in practice.
  • EP-A-0255443 discloses surfactants, typically for use in pharmaceutical preparations, having a polyhydroxylated hydrophilic moiety, a highly fluorinated moiety and a functional junction group linking the moieties together. Included in the disclosure of EP-A- 0255443 are compounds of general formula B:
  • R f CsFn , C F 15 or C 8 F 1
  • EP-A-0255443 further discloses a process for preparation of the compounds thereof.
  • the process involves reacting a polyol or aminopolyol in which the hydroxy groups, or part thereof, are protected, with a highly fluorinated derivative so as to link the polyol or aminopolyol moiety with the highly fluorinated moiety through a functional junction group.
  • the highly fluorinated derivative may be an alcohol, an amine, an anhydride, a mixed anhydride or an acyl chloride.
  • Compounds of general formula B are synthesised by reacting glucamide with an acid anhydride derivative of the highly fluorinated moiety.
  • the present invention sets out to provide fabric treatment compositions which use perfluoroalkyl amphiphilic compounds which are easy to synthesise and which give water, soil and oil repellency to fabric.
  • the present invention further sets out to provide perfluoroalkyl amphiphilic compounds which are simple to synthesise.
  • the present invention provides fabric treatment compositions comprising a perfluoroalkyl amphiphilic compound of general formula (I) : Rf-A- C ( O) -N (R) - CH 2 ( CHOH) 4 CH 2 OH ( I )
  • m an integer in the range 3-20, preferably 4-18, and X is a halogen atom, wherein at least 50% of the halogen atom X are fluorine atoms and the reminder are chlorine or bromine atoms,
  • A is a divalent linking group
  • R is a hydrogen atom or a Ci-C ⁇ alkyl or alkenyl group .
  • perfluoroalkyl glucamides are relatively easy to synthesise because of the amide bond.
  • the amide bond is found to be stable on storage.
  • the compounds are found to give excellent soil and oil repellency to cotton and polyester fabrics, and water repellency to polyester fabrics .
  • the present invention provides the use of a perfluoroalkyl amphiphilic compound according to general formula (I) above in a method of polyester fabric treatment, to give oil, soil and water repellency to the polyester fabric.
  • the present invention provides the use of a perfluoroalkyl amphiphilic compound according to general formula (1) above in a method of cotton fabric treatment, to give oil and soil repellency to the cotton fabric .
  • the present invention provides a method of treating a fabric comprising applying a fabric treatment composition comprising the perfluoralkyl amphiphilic compound of general formula (I) above to the fabric.
  • the present invention provides a perfluoroalkyl amphiphilic compound of general formula (III) :
  • R f and A have the meanings given in relation to general formula (I) above and R is a C ! -C 18 alkyl or alkenyl group .
  • the perfluoroalkyl group R f is a highly fluorinated moiety wherein at least 50% of the atoms bonded to the carbon skeleton are fluorine atoms, the other atoms bonded to the carbon skeleton being hydrogen, chlorine or bromine atoms. Preferably, there are at least four fluorine atoms.
  • the perfluoroalkyl group R f is preferably of general formula C q F 2q - H or C q F q Cl-, wherein q is an integer in the range 3-12. It is preferred that q is in the range 4-12, more preferably 6-12, most preferably 8-10.
  • the divalent linking group A is preferably selected from Ci-Cis alkylene, 1,4 phenylene or 1,4 phenylene substituted with at least one group selected from Ci-C 18 alkyl, C ⁇ -C 18 alkoxy, halogen (preferably F) or-S0 3 Na the C ⁇ -C 18 alkylene chains or 1,4 phenyl chains being optionally interrupted by -O- .
  • Particularly preferred linking groups are alkylene groups of general formula (V) :
  • Straight chain perfluoralkyl glucamides are known from EP-A-0255443 , but branched chain perfluoroalkyl glucamides are novel and a further subject of the present invention.
  • R is an alkyl or alkenyl group, which is suitably straight but may be branched. It may have from 1-18 carbon atoms, more preferably 1-12 carbon atoms, and most preferably 1-8 carbon atoms. It may be substituted, for example with OH or halogen atoms.
  • perfluoroalkyl glucamides of use in the present invention comprise perfluoroalkyl glucamides of general formula (VI) :
  • Perfluoroalkyl glucamides according to the present invention may be manufactured by the process disclosed in EP-A-0255443. Alternatively, the novel method of synthesis of the present invention may be used.
  • the novel synthesis route according to the present invention employs an amidation reaction between an ester derivative of a perfluoroalkyl compound and N-alkyl glucamine .
  • ester derivatives can be obtained by any suitable method.
  • ester derivatives are methyl esters.
  • ester derivatives may however be obtained by reacting a perfluoroalkyl halide with an alkenoic acid ester under suitable conditions:
  • R f Y+CH 2 CH . B . C0 2 Ri ⁇ R f CH 2 CH 2 -B-C0 2 R ⁇
  • R f has the meaning given above
  • linking group B is a linking group which may be selected from the same group from which linking group A is selected, and
  • Ri has the meaning set out above .
  • Ri is methyl.
  • the linking group B is -(CH 2 ) n -, wherein n is in the range 0-16, preferably 0-10.
  • Y is a halogen atom, preferably iodine.
  • Halogen derivatives of perfluoroalkyl groups are available in the art and can be obtained from Acros Organics or Fisher Scientific Company.
  • N-alkyl glucamines are available in the art from Aldrich Company.
  • reaction can be synthesised by reducing glucose in the presence of primary amine .
  • the following reaction may be used:
  • R has the meaning set out above .
  • the reduction is suitably carried out by hydrogenation in the presence of a suitable catalyst, for example Raney Nickel .
  • the present invention is suitable for use in industrial or domestic fabric wash compositions, fabric conditioning compositions and compositions for both washing and conditioning fabrics (so-called through the wash conditioner compositions) .
  • the present invention can also be applied to industrial or domestic non-detergent based fabric care compositions, for example spray-on compositions.
  • Perfluoroalkyl amphiphilic compounds are suitably present in the fabric care compositions of the present invention at levels in excess of 0.2% by weight, preferably greater than 0.4% by weight. They are preferably present at levels less than 1.5% by weight and preferably less than 1.2% by weight .
  • Fabric wash compositions according to the present invention may be in any suitable form, for example powdered, tableted powders, liquid or solid detergent bars.
  • Fabric wash compositions according to the present invention comprise a fabric wash detergent material selected from non-soap anionic surfactant, nonionic surfactants, soap, amphoteric surfactants, zwitterionic surfactants and mixtures thereof .
  • Suitable anionic surfactants are well known to the person skilled in the art and include alkyl benzene sulphonate, primary and secondary alkyl sulphates, particularly C 8 -C 15 primary alkyl sulphates; alkyl ether sulphates; olefin sulphonates; alkyl xylene sulphonates, dialkyl sulphosuccinates; ether carboxylates; isethionates; sarcosinates; fatty acid ester sulphonates and mixtures thereof.
  • the sodium salts are generally preferred.
  • Nonionic surfactants are also well known to the person skilled in the art and include primary and secondary alcohol ethoxylates, especially C 8 -C 20 aliphatic alcohol ethoxylated with an average of from 1 to 20 moles of ethylene oxide per mole of alcohol, and more especially the C ⁇ o-C 15 primary and secondary aliphatic alcohol ethoxylated with an average of from 1 to 10 moles of ethylene oxide per mole of alcohol.
  • Non-ethoxylated nonionic surfactants include alkyl polyglycosides, glycerol monoethers and polyhydroxy amides (glucamide) . Mixtures of nonionic surfactant may be used.
  • Detergent compositions suitable for use in domestic or industrial automatic fabric washing machines generally contain anionic non-soap surfactant or nonionic surfactant, or combinations of the two in suitable ratio, as will be known to the person skilled in the art, optionally together with soap.
  • Anionic surfactant is suitably present at a level of from 5 wt% to 50 wt%, preferably 10 wt%-40 wt% based on the fabric treatment composition.
  • Nonionic surfactant is suitably present at a level of 1-20 wt%, preferably 5-15 wt%.
  • the total amount of surfactant present will depend upon the intended end use and may be as high as 60 wt% for example in a composition for washing fabrics by hand. In compositions for machine washing of fabric, an amount of from 5 to 40 wt% is generally appropriate.
  • the detergent compositions of the invention will generally also contain one or more detergency builders.
  • the total amount of detergency builder in the compositions will suitably range from 5 to 80 wt%, preferably from 10 to 60 wt%.
  • Inorganic builders that may be present include sodium carbonate, if desired in combination with a crystallisation seed for calcium carbonate, as disclosed in GB 1 437 950 (Unilever ) ; crystalline and amorphous aluminosilicates, for example, zeolites as disclosed in GB 1 473 202 (Henkel) and mixed crystalline/amorphous aluminosilicates as disclosed in GB 1 470 250 (Procter & Gamble) ; and layered silicates as disclosed in EP 164 514B (Hoechst) .
  • Inorganic phosphate builders for example, sodium orthophosphate, pyrophosphate and tripolyphosphate are also suitable for use with this invention.
  • the detergent compositions of the invention preferably contain an alkali metal, preferably sodium, aluminosilicate builder.
  • Sodium aluminosilicates may generally be incorporated in amounts of from 10 to 70% by weight (anhydrous basis), preferably from 25 to 50 wt%.
  • the alkali metal aluminosilicate may be either crystalline or amorphous or mixtures thereof, having the general formula:
  • the preferred sodium aluminosilicates contain 1.5- 3.5 Si0 2 units (in the formula above) . Both the amorphous and the crystalline materials can be prepared readily be reaction between sodium silicate and sodium aluminate, as amply described in the literature.
  • Suitable crystalline sodium aluminosilicate ion-exchange detergency builders are described, for example, in GB 1 429 143 (Procter & Gamble) .
  • the preferred sodium aluminosilicates of this type are the well-known commercially available zeolites A and X, and mixtures thereof .
  • the zeolite may be the commercially available zeolite 4A now widely used in laundry detergent powders.
  • the zeolite builder incorporated in the compositions of the invention may be maximum aluminium zeolite P (zeolite MAP) as described and claimed in EP 384 070A (Unilever) .
  • Zeolite MAP is defined as an alkali metal aluminosilicate of the zeolite P type having a silicon to aluminium ratio not exceeding 1.33, preferably within the range of from 0.90 to 1.33, and more preferably within the range of from 0.90 to 1.20.
  • zeolite MAP having a silicon to aluminium ratio not exceeding 1.07, more preferably about 1.00.
  • the calcium binding capacity of zeolite MAP is generally at least 150 mg CaO per g of anhydrous material.
  • Organic builders that may be present include polycarboxylate polymers such as polyacrylates, acrylic/maleic copolymers, and acrylic phosphinates; monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di- and trisuccinates, carboyxmethyloxysuccinates , carboxymethyloxymalonates , dipicolinates, hydroyxethyliminodiacetates, alkyl- and alkenylmalonates and succinates, ; and sulphonated fatty acid salts. This list is not intended to be exhaustive.
  • polycarboxylate polymers such as polyacrylates, acrylic/maleic copolymers, and acrylic phosphinates
  • monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di- and trisuccinates, carboyxmethyloxysuccinates , carboxymethyloxymalonates
  • Especially preferred organic builders are citrates, suitable used in amounts of from 5 to 30 wt%, preferably from 10 to 25 wt%; and acrylic polymers, more especially acrylic/maleic copolymers, suitably used in amounts of from 0.5 to 15 wt%, preferably from 1 to 10 wt%.
  • Builders both inorganic and organic, are preferably present in alkali metal salt, especially sodium salt, form.
  • Detergent compositions according to the invention may also suitably contain a peroxy bleach system for example, inorganic persalts or organic peroxyacids, capable of yielding hydrogen peroxide in aqueous solution.
  • a peroxy bleach system for example, inorganic persalts or organic peroxyacids, capable of yielding hydrogen peroxide in aqueous solution.
  • Suitable peroxy bleach compounds include organic peroxides such as urea peroxide, and inorganic persalts such as the alkali metal perborates, percarbonates, perphosphates, persilicates and persulphates .
  • organic peroxides such as urea peroxide
  • inorganic persalts such as the alkali metal perborates, percarbonates, perphosphates, persilicates and persulphates .
  • Preferred inorganic persalts are sodium perborate monohydrate and tetrahydrate, and sodium percarbonate .
  • sodium percarbonate having a protective coating against destabilisation by moisture Especially preferred is sodium percarbonate having a protective coating against destabilisation by moisture.
  • Sodium percarbonate having a protective coating comprising sodium metaborate and sodium silicate is disclosed in GB 2 123 044B (Kao) .
  • compositions may further comprise a photobleach system as described, for example, in EP-A-0035470.
  • Fabric Softening Composition
  • the fabric treatment composition of the present invention may be a fabric conditioning composition or it may comprise fabric conditioner.
  • the fabric softening compound is preferably a cationic nonionic or anionic fabric softening compound.
  • the fabric softening compound may be a quaternary ammonium material comprising a polar head group and one or two alkyl or alkenyl chains.
  • the fabric softening compound may also be a nonionic fabric softening compound such as a fabric softening oil, a fabric softening silicone composition or a fabric softening ester composition such as sugar esters.
  • the fabric softening compound has two long chain alkyl or alkenyl chains with an average chain length greater than C 14 , more preferably each chain has an average chain length greater than C 14 , more preferably at least 50% of each long chain alkyl or alkenyl group has a chain length of C 18 .
  • the long chain alkyl or alkenyl groups of the fabric softening compound are predominantly linear.
  • the fabric softening compounds are substantially water-insoluble.
  • Substantially insoluble fabric softening compounds in the context of this invention are defined as fabric softening compounds having a solubility less than 1 x 10 " wt% in demineralised water at 20°C, preferably the fabric softening compounds have a solubility less than 1 x 10 " , most preferably the fabric softening compounds have a solubility at 20°C in demineralised water from 1 x 10 " to 1 x 10 "6 .
  • R 1 and R 2 represent hydrocarbyl groups having from 12 to 24 carbon atoms; R 3 and R represent hydrocarbyl groups containing 1 to 4 carbon atoms; and X is an anion, preferably selected from halide, methyl sulphate and ethyl sulphate groups are preferred.
  • quaternary softeners include di (tallow alkyl) dimethyl ammonium methyl sulphate; dihexadecyl dimethyl ammonium chloride; di (hydrogenated tallow alkyl) dimethyl ammonium chloride; dioctadecyl dimethyl ammonium chloride; di (hydrogenated tallow alkyl) dimethyl ammonium methyl sulphate; dihexadecyl diethyl ammonium chloride; di (coconut alkyl) dimethyl ammonium chloride, ditallow alkyl dimethyl ammonium chloride and di (hydrogenated tallow alkyl) dimethyl ammonium chloride (Arquad 2HT Trade Mark) .
  • esters or amide links for example those available under the trade names Accosoft 580, Varisoft 222, and Stepantex.
  • Particularly preferred fabric softening compounds are water-insoluble quaternary ammonium materials which comprise a compound having two C 12-18 alkyl or alkenyl groups connected to the molecule via at least one ester link. It is more preferred if the quaternary ammonium material has two ester links present.
  • the preferred ester-linked quaternary ammonium material for use in the invention can be represented by the formula:
  • each R group is independently selected from C 1-4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein each R group is independently selected from C 8-28 alkyl or alkenyl groups; O O
  • T is -C-O- or -0-C-;
  • X is any suitable anion and n is an integer from 0-5. Particularly preferred is di (ethyl ester) dimethyl ammonium chloride (DEEDMAC) .
  • a second preferred type of quaternary ammonium material can be represented by the formula :
  • R l7 n, X " and R 2 are as defined above.
  • Preferred materials of this class such as 1,2 bis [hardened tallowoyloxy] -3-trimethylammonium propane chloride and their methods of preparation are, for example, described in US 4 137 180 (Lever Brothers) .
  • these materials comprise small amounts of the corresponding monoester as described in US 4 137 180 for example 1-hardened tallowoyloxy-2-hydroxy trimethylammonium propane chloride.
  • the fabric softening agent may also be a polyol ester quat (PEQ) as described in EP 0 638 639 (Akzo) .
  • PEQ polyol ester quat
  • compositions of the invention can also contain one or more optional ingredients, selected from pH buffering agents, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti- shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • optional ingredients selected from pH buffering agents, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti- shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • the present invention may be in the form of a dilute or concentrated aqueous solution or suspension, for example as described in WO 97/15651, WO 95/27769.
  • the fabric softening composition may be in the form of a powder for use in the rinse cycle of an automatic washing machine.
  • the fabric softening composition may be in the form of a sheet comprising fabric conditioning compositions for use in a tumble dryer, for example as disclosed in WO 95/27777.
  • Fabric wash detergent compositions according to the present invention may further include through the wash softening material, such as cationic fabric softener.
  • the present invention can also be used in non-detergent- based fabric care products.
  • the product may comprise the stain removal system as the principal ingredient.
  • non-detergent based compositions may comprise solutions of the stain removal system of the present invention in a suitable solvent, such as isopropanol, alcohol etc.
  • the compositions may comprise aerosol or spray-on compositions. They may be in the form of sticks, bars, dab-on compositions, for example absorbed into sponges for application to the surface etc.
  • N-alkyl glucamine (RNHCH 2 (CHOH) 4 CH 2 OH) in 10 ml anhydrous CH 3 OH was heated to 70-80°C in a nitrogen atmosphere before addition of RfCH 2 CH 2 COOCH 3 and NaOCH 3 (0.05 mmol, 0.955 M) . Reaction was continued at 70-80°C for 20 hours. Additional methanol was added to dissolve the solids. Then, Dowex (trade mark) resin (H ) was added and stirred for 30 minutes. After removal of the resin and solvent, the residue was purified by column chromatography (eluted with trichloromethane, followed by a 1:9 by volume mixture of methanol and trichloromethane) . Further purification by recrystallisation yielded products as white solids.
  • Polyester was pre-treated with IN Na 2 C0 3 and boiled for 15 minutes. It was then washed with distilled water until neutral. It was boiled again in distilled water for 15 minutes, after which it was dried in a 65 °C oven for 30 minutes .
  • the cotton cloth was treated similarly except that it was boiled for 30 minutes with sodium carbonate instead of 15 minutes .
  • test cloths were then each immersed in a methanol or ethanol solution of perfluoroalkyl glucamide for 1 hour and then taken out of the methanol or ethanol solution and dried at 40°C for 30 minutes.
  • Oil repellency was measured at 15°C using a red-coloured oil (cooking oil flavoured with chilli) . A 0.01 ml oil droplet was applied to the treated fabric surface. Effectiveness of repellency was assessed by determining how quickly the droplet spread.
  • LAS and MEGA provide no oil repellency even at relatively high concentration in solvent .
  • Fluorinated surfactant provides weak soil repellency at very high concentrations in solvent.
  • Polyester and cotton test cloths of 4.0cm by 4.0cm were used.
  • the polyester was pre-treated with IN NaC0 3 and boiled for 15 minutes . It was then washed with distilled water until neutral . It was boiled again in distilled water for 15 minutes after which it was dried in a 65°C oven for 30 minutes .
  • the cotton cloth was treated similarly except that it was boiled for 30 minutes with sodium carbonate instead of 15 minutes .
  • the test cloths were then each immersed in an ethanol solution of perflouro alkyl glucamide for one hour.
  • the test cloths were dried at 40°C for 30 minuets.
  • Water repellency was measured at room temperature using coloured water. The persistence of a 0.01 ml water droplet on the fabric determined the effectiveness of repellency. If the droplet permeates the fabric quickly, there is no repellency. If the droplets spread slowly, repellency is weak. If the droplet maintains a high contact angle, repellency is high.
  • perfluoalkyl glucamides do not do not provide water repellency for cotton, but do provide water repellency for polyester at concentrations up to 0.5 weight percent .
  • N-Alkyl perfluoroalkl glucamides were stored at room temperature for three years. Stability was assessed by comparing NMR, ESI and IR spectra before and after storage. Good stability of the compounds was demonstrated by these spectra.
  • a detergent solution comprising 0.6 grams of linear alkyl benzene sulfonate, 0.6 grams per litre of sodium tripolyphosphate, 0.3 grams of sodium carbonate and 1.5 grams of sodium sulphate at room temperature was prepared.
  • Perfluoroakyl glucamides were dissolved at a level of 0.1 wt% in this detergent solution.
  • Test cloths were prepared by the same method as used in the oil and water repellency tests. The cloths were immersed in ten ml of the detergent solution containing 0.1% perflouralkyl glucamide at room temperature for 1 hour and then washed under agitation in 200ml of distilled water for ten minutes. The deposition of N-perfluoroalkyl glucamide was assessed by measuring oil repellency after washing and drying . Tests were repeated for N-alkyl perfluoalkyl glucamides having alkyl chain lengths from C ⁇ -C 10 . All showed significant oil repellency on cotton and polyester after washing once with water. The oil repellency did not decrease after washing once more with water. Perfluoroalkyl glucamides deposit well on to fabric and are not easily rinsed off.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composants de formule générale (I): Rf-A-C(O)-N(R)-CH2-(CHOH)4CH2OH, dans laquelle : Rf représente un groupe de formule (II): (CmX2m+1)-, dans laquelle m est un nombre entier compris entre 3 et 12, de préférence entre 6 et 10, et X représente un atome d'halogène, dans laquelle au moins 50 % des atomes d'halogène X sont des atomes de fluor, le reste étant des atomes de chlore ou de brome, A représentant un groupe de liaison divalent, et R représente un atome d'hydrogène ou un groupe alkyle ou alkényle C1-C18. Ces composants permettent à des tissus d'offrir une résistance à l'huile, à la terre et à l'eau. Ces composants peuvent entrer dans des compositions de traitement de tissus. Les compositions établies conformément à la formule générale (I) mais dans laquelle R représente un groupe alkyle ou alkényle C1-C18 sont des nouveaux composants.
PCT/EP2001/006376 2000-07-17 2001-06-05 Composition de traitement de tissus et procede de traitement de tissus et composants amphiphiles perfluoroalkyles WO2002006580A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001279644A AU2001279644A1 (en) 2000-07-17 2001-06-05 Fabric treatment composition, method of treating fabric and perfluoroalkyl amphiphilic compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0017520A GB2364702A (en) 2000-07-17 2000-07-17 Perfluoroalkyl amphiphilic fabric treatment compounds
GB0017520.8 2000-07-17

Publications (1)

Publication Number Publication Date
WO2002006580A1 true WO2002006580A1 (fr) 2002-01-24

Family

ID=9895812

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/006376 WO2002006580A1 (fr) 2000-07-17 2001-06-05 Composition de traitement de tissus et procede de traitement de tissus et composants amphiphiles perfluoroalkyles

Country Status (3)

Country Link
AU (1) AU2001279644A1 (fr)
GB (1) GB2364702A (fr)
WO (1) WO2002006580A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7893014B2 (en) 2006-12-21 2011-02-22 Gregory Van Buskirk Fabric treatment for stain release
CN106946719A (zh) * 2017-03-15 2017-07-14 西安楚龙达化工有限公司 一种非离子型Gemini表面活性剂及其合成方法
US10822577B2 (en) 2002-04-09 2020-11-03 Gregory van Buskirk Fabric treatment method for stain release
US10900168B2 (en) 2002-04-09 2021-01-26 Gregory van Buskirk Fabric treatment for stain repellency

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4089804A (en) * 1976-12-30 1978-05-16 Ciba-Geigy Corporation Method of improving fluorinated surfactants
EP0240601A1 (fr) * 1986-04-04 1987-10-14 Hoechst Aktiengesellschaft Polyalcools fluorés, procédé pour leur préparation et leur utilisation
EP0255443A1 (fr) * 1986-07-29 1988-02-03 Atta Composés polyhydroxylés et hautement fluorés, leur synthèse et leur utilité comme agents tensio-actifs
EP0375610A2 (fr) * 1988-12-19 1990-06-27 Ciba-Geigy Ag Perfluoroalkylthioglycosides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19914101C1 (de) * 1999-03-22 2000-10-12 Schering Ag Perfluoralkylamide, ihre Herstellung und ihre Verwendung in der Diagnostik

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4089804A (en) * 1976-12-30 1978-05-16 Ciba-Geigy Corporation Method of improving fluorinated surfactants
EP0240601A1 (fr) * 1986-04-04 1987-10-14 Hoechst Aktiengesellschaft Polyalcools fluorés, procédé pour leur préparation et leur utilisation
EP0255443A1 (fr) * 1986-07-29 1988-02-03 Atta Composés polyhydroxylés et hautement fluorés, leur synthèse et leur utilité comme agents tensio-actifs
EP0375610A2 (fr) * 1988-12-19 1990-06-27 Ciba-Geigy Ag Perfluoroalkylthioglycosides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
EDWARDS C M ET AL.: "Novel fluorosurfactants for perfluorochemical emulsification", ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY, SPRING ST., NY, US, vol. 428, 1997, pages 489 - 493, XP001041396 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10822577B2 (en) 2002-04-09 2020-11-03 Gregory van Buskirk Fabric treatment method for stain release
US10900168B2 (en) 2002-04-09 2021-01-26 Gregory van Buskirk Fabric treatment for stain repellency
US7893014B2 (en) 2006-12-21 2011-02-22 Gregory Van Buskirk Fabric treatment for stain release
CN106946719A (zh) * 2017-03-15 2017-07-14 西安楚龙达化工有限公司 一种非离子型Gemini表面活性剂及其合成方法

Also Published As

Publication number Publication date
GB0017520D0 (en) 2000-08-30
AU2001279644A1 (en) 2002-01-30
GB2364702A (en) 2002-02-06

Similar Documents

Publication Publication Date Title
US5922663A (en) Enhancement of soil release with gemini surfactants
US6040288A (en) Fabric color protection compositions and methods
CA2021322C (fr) Composition d'assouplisseur de tissu
CA2021010C (fr) Assouplisseur de tissus
US7572761B2 (en) Process for cleaning and softening fabrics
US5858960A (en) Fabric softening composition
US5077119A (en) Fabric conditioning
WO2001007550A1 (fr) Composition de traitement du tissu et procede de traitement
AU757696B2 (en) Fabric care treatment composition and a method of treating fabric
CN104145012A (zh) 丙烯酸酯共聚物作为抗污垢再沉积剂和去污剂在洗衣过程中的用途
CA2408114C (fr) Composition adoucissante pour tissus comprenant un compose adoucissant pour tissus sans groupe azote quaternaire cationique
WO2002006580A1 (fr) Composition de traitement de tissus et procede de traitement de tissus et composants amphiphiles perfluoroalkyles
EP0687723A1 (fr) Molécules dérivées du glycérol et de la bétaine pour le conditionnement de matières textiles
EP1592761B1 (fr) Méthode pour le blanchiment
CA2151319C (fr) Molecules de conditionnement biodegradables a base d'acide glycerique pour tissus
CA2374315A1 (fr) Amelioration de la viscosite et des proprietes d'assouplissement de produits assouplissants de cycle de rincage, a faible teneur en solides, a base de composes d'ammonium quaternaire et d'ethoxylates d'amine
WO2001044424A1 (fr) Composition d'entretien de tissus
WO2002006433A1 (fr) Composition de lessive comprenant un polymere antisalissure a base de perfluoroalkyle
WO1998028390A1 (fr) Compositions de produit d'assouplissement
EP1539907A1 (fr) Preparation de conditionnement de tissus

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP