WO2011064562A2 - Produit et procédé innovant - Google Patents

Produit et procédé innovant Download PDF

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Publication number
WO2011064562A2
WO2011064562A2 PCT/GB2010/051619 GB2010051619W WO2011064562A2 WO 2011064562 A2 WO2011064562 A2 WO 2011064562A2 GB 2010051619 W GB2010051619 W GB 2010051619W WO 2011064562 A2 WO2011064562 A2 WO 2011064562A2
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WO
WIPO (PCT)
Prior art keywords
formula
fabric
group
yarn
fibre
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PCT/GB2010/051619
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English (en)
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WO2011064562A3 (fr
WO2011064562A8 (fr
Inventor
Christopher Carr
Akbar Khoddami
Stephen Coulson
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P2I Ltd
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.)
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Publication date
Application filed by P2I Ltd filed Critical P2I Ltd
Priority to CA2780700A priority Critical patent/CA2780700A1/fr
Priority to US13/512,064 priority patent/US20130117978A1/en
Priority to JP2012540495A priority patent/JP2013512352A/ja
Priority to CN2010800624166A priority patent/CN102844490A/zh
Priority to AU2010322855A priority patent/AU2010322855B2/en
Priority to EP10769045A priority patent/EP2510147A2/fr
Priority to NZ600440A priority patent/NZ600440A/en
Publication of WO2011064562A2 publication Critical patent/WO2011064562A2/fr
Publication of WO2011064562A3 publication Critical patent/WO2011064562A3/fr
Publication of WO2011064562A8 publication Critical patent/WO2011064562A8/fr
Priority to IL219873A priority patent/IL219873A0/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
    • D06M10/00—Physical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. ultrasonic, corona discharge, irradiation, electric currents, or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/02—Physical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. ultrasonic, corona discharge, irradiation, electric currents, or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements ultrasonic or sonic; Corona discharge
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06C—FINISHING, DRESSING, TENTERING OR STRETCHING TEXTILE FABRICS
    • D06C29/00—Finishing or dressing, of textile fabrics, not provided for in the preceding 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
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
    • D06M14/24—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of animal origin, e.g. wool or silk
    • 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
    • D06M10/00—Physical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. ultrasonic, corona discharge, irradiation, electric currents, or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/02—Physical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. ultrasonic, corona discharge, irradiation, electric currents, or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements ultrasonic or sonic; Corona discharge
    • D06M10/025—Corona discharge or low temperature plasma
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/77—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with silicon or compounds thereof
    • D06M11/79—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with silicon or compounds thereof with silicon dioxide, silicic acids or their salts
    • 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
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • 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
    • D06M2101/10—Animal fibres
    • D06M2101/12—Keratin fibres or silk
    • 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
    • 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
    • D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
    • 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
    • D06M2200/45—Shrinking resistance, anti-felting properties

Definitions

  • the present invention relates to the treatment of wool and wool blend fabrics to improve laundering performance, in particular to reduce shrinkage due to felting during laundering.
  • 'wool' includes not only the fibres derived from the Caprinae family, such as sheep, but also the hair of certain other species of mammals, such as goats, llamas, alpacas and rabbits (e.g. cashmere, mohair or angora) . lar material for mak
  • the problem of shrinkage is due to felting caused by wool fibre's complex structure, consisting on an inner cortex and outer surface cuticle. It is this outer surface cuticle which is primarily responsible for felting shrinkage.
  • the cuticle comprises an epicuticle which includes fatty lipids covalently bound to a protein surface, which provide some natural water repellency.
  • the cuticle also comprises an
  • exocuticle which has a rigid surface structure comprising of overlapping scales which protect the wool fibre from mechanical damage.
  • This rigid surface structure of the exocuticle is responsible for a 'directional frictional effect' (DFE) which leads to wool felting during laundering.
  • the major method of treating wool to make it machine washable is the chlorine Hercosett process, which aims to "mask and smooth" the surface scales hence eliminating the DFE.
  • the process involves a series of aqueous baths; starting with acid
  • chlorination to modify the epicuticle and thereby impart wettability, create reactive functionality for the reactive polymer bonding and raise surface energy to allow the polymer coating to spread.
  • a subsequent step is antichlorination / neutralisation which creates further reactive functionality for the reactive polymer bonding and removes residual chlorine from the fibre. This step is followed by application of the polymer, softening and drying.
  • the Hercosett polymer is a soft, cationic reactive
  • epichlorohydrin polyamide which exhausts onto the negatively charged wool fibre and covalently bonds to the fibre surface. It masks the scale edges so eliminating the DFE.
  • Chlorine Hercosett process is described in more detail in T. Shaw & M. A. White, Chapter 5, P.346 (1984), Handbook of Fiber Science & Fiber Technology, Vol. II, Chemical Processing of Fibers & Fabrics, Functional Finishes, Part B, Edited by M. Lewin & S. B. Sello. Marcel Dekker Inc., New York. ISBN 0-8247- 7118.
  • the Chlorine Hercosett process is also described in both J. Lewis, Wool Science Review, 54, 2 (1977) and also H. J. Katz, G. F. Wood & M.T. Goldsmith, Textile Manufacturer, 95, 84
  • the Chlorine Hercosett process has the disadvantage that adsorbable organohalogens (AOX) are produced in the chlorination stage, causing other solutions to be sought.
  • AOX adsorbable organohalogens
  • Durable water repellent coatings are often added to fabrics to make them water resistant, for example Fluoropel and Olephobol are two typical fluoropolymers coatings applied by wet chemistry techniques to give water repellency. Durable water repellent coatings are discussed in E. Kissa, Chapter 2, P.143 (1984), Handbook of Fiber Science & Fiber Technology, Vol. II, Chemical Processing of Fibers & Fabrics, Functional Finishes, Part B, Edited by M. Lewin & S. B. Sello. Marcel Dekker Inc., New York. ISBN 0-8247-7118 and also F. Audenaert, H. Lens, D. Roily and P. Van der Elst, Fluorochemical Textile Repellents - Synthesis, and Applications: A 3M Perspective, J. Text. Inst., 90, 3, 76 (1999) .
  • Plasma deposition techniques have been used for the deposition of polymeric coatings onto a range of surfaces, and in
  • This technique is recognised as being a clean, dry technique that generates little waste compared to conventional wet chemical methods.
  • plasmas are generated from organic molecules, which are subjected to an electrical field. When this is done in the presence of a substrate, the radicals of the compound in the plasma polymerise on the substrate.
  • Conventional polymer synthesis tends to produce structures containing repeat units that bear a strong resemblance to the monomer species, whereas a polymer network generated using a plasma can be extremely complex.
  • the properties of the resultant coating can depend upon the nature of the substrate as well as the nature of the monomer used and conditions under which it is deposited.
  • a first aspect of the present invention provides a method of treating wool in the form of fibre, sliver, yarn, fabric or garment comprising said fibre or yarn, to prevent shrinkage due to felting during laundering, the method comprising applying a polymer coating by plasma polymerisation.
  • a sliver is carded and combed wool formed into a tube of fibres.
  • the Textile Institute define a sliver as an assemblage of fibres in continuous form without twist.
  • the fibre, yarn, sliver, fabric or garment may comprise pure wool or a wool / polymer blend.
  • any monomer that undergoes plasma polymerisation or modification of the surface to form a suitable polymeric coating layer may suitably be used.
  • monomers include those known in the art to be capable of producing hydrophobic polymeric coatings on substrates by plasma polymerisation including, for example, carbonaceous compounds having reactive functional groups, particularly substantially -CF 3 dominated perfluoro compounds (see WO 97/38801), perfluorinated alkenes (Wang et al . , Chem Mater 1996, 2212-2214), hydrogen containing
  • unsaturated compounds optionally containing halogen atoms or perhalogenated organic compounds of at least 10 carbon atoms (see WO 98/58117), organic compounds comprising two double bonds (WO 99/64662), saturated organic compounds having an optionally substituted alky chain of at least 5 carbon atoms optionally interposed with a heteroatom (WO 00/05000), optionally
  • a particular group of monomers which may be used to produce the coating of the present invention include compounds of formula
  • R 1 , R 2 and R 3 are independently selected from hydrogen, halo, alkyl, haloalkyl or aryl optionally substituted by halo; and R 4 is a group -X-R 5 where R 5 is an alkyl or haloalkyl group and X is a bond; a group of formula -C(0)0-, a group of formula -C (0) 0 (CH 2 ) n Y ⁇ where n is an integer of from 1 to 10 and Y is a sulphonamide group; or a group - (0) P R 6 (0) q (CH 2 ) t ⁇ where R 6 is aryl optionally substituted by halo, p is 0 or 1, q is 0 or 1 and t is 0 or an integer of from 1 to 10, provided that where q is 1, t is other than 0.
  • halo or “halogen” refers to fluorine chlorine, bromine and iodine. Particularly preferred halo groups are fluoro.
  • aryl refers to aromatic cyclic groups such as phenyl or naphthyl, in particular phenyl.
  • alkyl refers to straight or branched chains of carbon atoms, suitably of up to 20 carbon atoms in length.
  • alkenyl refers to straight or branched unsaturated chains suitably having from 2 to 20 carbon atoms.
  • Haloalkyl refers t alkyl chains as defined above which include at least one halo substituent .
  • Suitable haloalkyl groups for R 1 , R 2 , R 3 and R 5 are fluoroalkyl groups.
  • the alkyl chains may be straight or branched and may include cyclic moieties.
  • the alkyl chains suitably comprise 2 or more carbon atoms, suitably from 2-20 carbon atoms and preferably from 4 to 12 carbon atoms.
  • alkyl chains are generally preferred to have from 1 to 6 carbon atoms.
  • R 5 is a haloalkyl, and more preferably a perhaloalkyl group, particularly a perfluoroalkyl group of formula C m F 2m +i where m is an integer of 1 or more, suitably from 1-20, and preferably from 4-12 such as 4, 6 or 8.
  • Suitable alkyl groups for R 1 , R 2 and R 3 have from 1 to 6 carbon atoms .
  • R 1 , R 2 and R 3 are hydrogen. In a particular embodiment R 1 , R 2 , R 3 are all hydrogen. In yet a further embodiment however R 3 is an alkyl group such as methyl or propyl .
  • Y-r n is an integer which provides a suitable spacer group.
  • n is from 1 to 5, preferably about 2.
  • Suitable sulphonamide groups for Y include those of formula - N(R 7 )S0 2 ⁇ where R 7 is hydrogen or alkyl such as Ci_ 4 alkyl, in particular methyl or ethyl.
  • the compound of formula (I) is a compound of formula (II)
  • the compound of formula (I) is an acrylate of formula (III)
  • CH 2 CR 7a C (0) 0 (CH 2 ) n R 5 (III) where n and R 5 as defined above in relation to formula (I) and R 7a is hydrogen, Ci-io alkyl, or Ci_i 0 haloalkyl .
  • R 7a is hydrogen or Ci_ 6 alkyl such as methyl.
  • a particular example of a compound of formula (III) is a compound of formula (IV)
  • R a is as defined above, and in particular is hydrogen and x is an integer of from 1 to 9, for instance from 4 to 9, and preferably 7.
  • the compound of formula (IV) is IH, IH, 2H, 2H-heptadecafluorodecylacrylate .
  • the polymeric coating is formed by exposing the fibre, yarn, sliver, fabric or garment to plasma comprising one or more organic monomeric compounds, at least one of which comprises two carbon-carbon double bonds for a sufficient period of time to allow a polymeric layer to form on the surface.
  • the compound with more than one double bond comprises a compound of formula (V)
  • R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are all independently selected from hydrogen, halo, alkyl, haloalkyl or aryl optionally substituted by halo; and Z is a bridging group.
  • Suitable bridging groups Z for use in the compound of formula (V) are those known in the polymer art.
  • Suitable optional substituents for bridging groups Z include perhaloalkyl groups, in particular perfluoroalkyl groups.
  • the bridging group Z includes one or more acyloxy or ester groups.
  • the bridging group of formula Z is a group of sub-formula (VI)
  • n is an integer of from 1 to 10, suitably from 1 to 3
  • each R 14 and R 15 is independently selected from hydrogen, halo, alkyl or haloalkyl .
  • R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are haloalkyl such as fluoroalkyl , or hydrogen. In particular they are all hydrogen.
  • the compound of formula (V) contains at least one haloalkyl group, preferably a perhaloalkyl group.
  • R 14 and R 15 are as defined above and at least one of R 14 or R 15 is other than hydrogen.
  • a particular example of such a compound is the compound of formula B.
  • the polymeric coating is formed by exposing the fibre, yarn, sliver , fabric or garment to plasma comprising a monomeric saturated organic compound, said compound comprising an optionally substituted alkyl chain of at least 5 carbon atoms optionally interposed with a heteroatom for a sufficient period of time to allow a polymeric layer to form on the surface.
  • saturated means that the monomer does not contain multiple bonds (i.e. double or triple bonds) between two carbon atoms which are not part of an aromatic ring.
  • heteroatom includes oxygen, sulphur, silicon or nitrogen atoms. Where the alkyl chain is interposed by a nitrogen atom, it will be substituted so as to form a secondary or tertiary amine. Similarly, silicons will be substituted appropriately, for example with two alkoxy groups .
  • Particularly suitable monomeric organic compounds are those of formula (VII)
  • R 21 is a group X-R 22 where R 22 is an alkyl or haloalkyl group and X is a bond or a group of formula - C (0) 0 (CH 2 ) X Y- where x is an integer of from 1 to 10 and Y is a bond or a sulphonamide group; or a group - (0) P R 23 (0) s (CH 2 ) t ⁇ where R 23 is aryl optionally substituted by halo, p is 0 or 1, s is 0 or 1 and t is 0 or an integer of from 1 to 10, provided that where s is 1, t is other than 0.
  • Suitable haloalkyl groups for R 16 , R 17 , R 18 , R 19 , and R 20 are fluoroalkyl groups.
  • the alkyl chains may be straight or
  • the alkyl chains suitably comprise 1 or more carbon atoms, suitably from 1-20 carbon atoms and preferably from 6 to 12 carbon atoms.
  • R 22 is a haloalkyl, and more preferably a perhaloalkyl group, particularly a perfluoroalkyl group of formula C z F 2z +i where z is an integer of 1 or more, suitably from 1-20, and preferably from 6-12 such as 8 or 10.
  • X is a group -C (0) 0 (CH 2 ) y Y-
  • y is an integer which provides a suitable spacer group.
  • y is from 1 to 5, preferably about 2.
  • Suitable sulphonamide groups for Y include those of formula - N(R 23 )S0 2 " where R 23 is hydrogen, alkyl or haloalkyl such as
  • Ci_ 4 alkyl in particular methyl or ethyl.
  • the monomeric compounds used preferably comprises a C 6 - 2 5 alkane optionally substituted by halogen, in particular a
  • the polymeric coating is formed by exposing the fibres, yarn, sliver, fabric or garment to plasma comprising an optionally substituted alkyne for a sufficient period to allow a polymeric layer to form on the surface.
  • the alkyne compounds used comprise chains of carbon atoms, including one or more carbon-carbon triple bonds.
  • the chains may be optionally interposed with a heteroatom and may carry substituents including rings and other functional groups.
  • Suitable chains which may be straight or branched, have from 2 to 50 carbon atoms, more suitably from 6 to 18 carbon atoms. They may be present either in the monomer used as a starting material, or may be created in the monomer on application of the plasma, for example by the ring opening
  • Particularly suitable monomeric organic compounds are those of formula (VIII)
  • R ⁇ -OC-X ⁇ R 25 (VIII) where R 24 is hydrogen, alkyl, cycloalkyl, haloalkyl or aryl optionally substituted by halo; X 1 is a bond or a bridging group; and R 25 is an alkyl, cycloalkyl or aryl group optionally
  • Suitable bridging groups X 1 include groups of formulae
  • R 26 is hydrogen, alkyl, cycloalkyl or aryl.
  • Particular alkyl groups for R 26 include Ci_ 6 alkyl, in particular, methyl or ethyl .
  • R 24 is alkyl or haloalkyl, it is generally preferred to have from 1 to 6 carbon atoms .
  • Suitable haloalkyl groups for R include fluoroalkyl groups.
  • the alkyl chains may be straight or branched and may include cyclic moieties.
  • R 24 is hydrogen.
  • R 25 is a haloalkyl, and more preferably a perhaloalkyl group, particularly a perfluoroalkyl group of formula C r F 2r+ i where r is an integer of 1 or more, suitably from 1-20, and preferably from 6-12 such as 8 or 10.
  • the compound of formula (VIII) is a compound of formula (IX)
  • R 27 is haloalkyl, in particular a perhaloalkyl such as a C 6 -i2 perfluoro group like C 6 Fi 3 .
  • the compound of formula (VIII) is a compound of formula (X)
  • the alkyne monomer used in the process is a compound of formula (XIV)
  • R 28 is hydrogen, alkyl, cycloalkyl, haloalkyl or aryl optionally substituted by halo
  • R 29 , R 30 and R 31 are independently selected from alkyl or alkoxy, in particular Ci_ 6 alkyl or alkoxy .
  • Preferred groups R 28 are hydrogen or alkyl, in particular Ci_ 6 alkyl.
  • Preferred groups R 29 , R 30 and R 31 are Ci_ 6 alkoxy in particular ethoxy .
  • the fibres, yarn, sliver, fabric or garment to be treated is placed within a plasma chamber together with the material to be deposited in a gaseous state, a glow discharge is ignited within the chamber and a suitable voltage is applied, which may be pulsed.
  • the polymeric coating may be produced under both pulsed and continuous-wave plasma deposition conditions but pulsed plasma may be preferred as this allows closer control of the coating, and so the formation of a more uniform polymeric structure.
  • the expression "in a gaseous state” refers gases or vapours, either alone or in mixture, as well as aerosols .
  • Precise conditions under which the plasma polymerization takes place in an effective manner will vary depending upon factors such as the nature of the polymer, the fibres, yarn, sliver, fabric or garment treated and will be determined using routine methods and/or the techniques.
  • Suitable plasmas for use in the method of the invention include non-equilibrium plasmas such as those generated by
  • radiofrequencies RF
  • microwaves microwaves or direct current (DC) .
  • DC direct current
  • RF radiofrequencies
  • Various forms of equipment may be used to generate gaseous plasmas. Generally these comprise containers or plasma chamber in which plasmas may be generated. Particular examples of such equipment are described for instance in WO2005/089961 and WO02/28548, but many other conventional plasma generating apparatus are available.
  • the gas present within the plasma chamber may comprise a vapour of the monomer alone, but it may be combined with a carrier gas in particular, an inert gas such as helium or argon, if required.
  • a carrier gas in particular, an inert gas such as helium or argon, if required.
  • helium is a preferred carrier gas as this can minimise fragmentation of the monomer.
  • the relative amounts of the monomer vapour to carrier gas are suitably determined in accordance with procedures which are conventional in the art.
  • the amount of monomer added will depend to some extent on the nature of the particular monomer being used, the nature of the substrate being treated, the size of the plasma chamber etc.
  • monomer is delivered in an amount of from 50-250mg/minute, for example at a rate of from 100- 150mg/minute . It will be appreciated however, that the rate will vary depending on the reactor size chosen and the number of substrates required to be processed at once; this in turn depends on considerations such as the annual through-put required and the
  • Carrier gas such as helium is suitably administered at a constant rate for example at a rate of from 5-90 standard cubic centimetres per minute (seem), for example from 15-30sccm.
  • the ratio of monomer to carrier gas will be in the range of from 100:0 to 1:100, for instance in the range of from 10:0 to 1:100, and in particular about 1:0 to 1:10. The precise ratio selected will be so as to ensure that the flow rate required by the process is achieved.
  • a preliminary continuous power plasma may be struck for example for from 15 seconds to 10 minutes, for example from 2-10 minutes within the chamber.
  • This may act as a surface pre-treatment step, ensuring that the monomer attaches itself readily to the surface, so that as polymerisation occurs, the coating "grows" on the surface .
  • the pre-treatment step may be conducted before monomer is introduced into the chamber, in the presence of only an inert gas.
  • the inert gas comprises argon.
  • the plasma is then suitably switched to a pulsed plasma to allow polymerisation to proceed, at least when the monomer is present.
  • a glow discharge is suitably ignited by applying a high frequency voltage, for example at 13.56MHz. This is applied using electrodes, which may be internal or external to the chamber, but in the case of larger chambers are generally internal .
  • the gas, vapour or gas mixture is supplied at a rate of at least 1 standard cubic centimetre per minute (seem) and preferably in the range of from 1 to lOOsccm.
  • this is suitably supplied at a rate of from 80-300mg/minute, for example at about
  • Gases or vapours may be delivered into the plasma chamber using any conventional method. For example, they may be drawn, injected or pumped into the plasma region. In particular, where a plasma chamber is used, gases or vapours may be drawn into the chamber as a result of a reduction in the pressure within the chamber, caused by use of an evacuating pump, or they may be pumped, sprayed, dripped, electrostatically ionised or injected into the chamber as is common in liquid handling.
  • Polymerisation is suitably effected using vapours of compounds for example of formula (I), which are maintained at pressures of from 0.1 to 400mtorr, suitably at about 10-lOOmtorr.
  • the applied fields are suitably of power of from 5 to 500W for example from 20 to 500W, suitably at about 100W peak power, applied as a continuous or pulsed field.
  • pulses are suitably applied in a sequence which yields very low average powers, for example in a sequence in which the ratio of the time on : time off is in the range of from 1:100 to 1:1500, for example at about 1:650.
  • Particular examples of such sequence are sequences where power is on for 20-50 s, for example about 30 ⁇ , and off for from ⁇ to 30000 ⁇ 3, in particular about 20000 s.
  • Typical average powers obtained in this way are 0.1 - 0.2 W.
  • the fields are suitably applied from 30 seconds to 90 minutes, preferably from 5 to 60 minutes, depending upon the nature of the compound of formula (I) and the fibres, yarn, sliver, fabric or garment being treated.
  • a plasma chamber used is of sufficient volume to accommodate multiple fibres, yarn, slivers, fabrics or garments.
  • the plasma is created with a voltage as a pulsed field, at an average power of from 0.001 to 500W/m 3 , for example at from 0.001 to 100W/m 3 and suitably at from 0.005 to 0.5W/m 3 .
  • These conditions are particularly suitable for depositing good quality uniform coatings, in large chambers, for example in chambers where the plasma zone has a volume of greater than 500cm 3 , for instance 0.1m 3 or more, such as from 0.5m 3 -10m 3 and suitably at about lm 3 .
  • the layers formed in this way have good mechanical strength.
  • the dimensions of the chamber will be selected so as to be selected so as to be selected so as to be selected.
  • elongate or rectangular chambers may be constructed or indeed cylindrical, or of any other suitable shape.
  • the chamber may be a sealable container, to allow for batch processes, or it may comprise inlets and outlets for the fibre, yarn, sliver, fabric or garment, to allow it to be utilised in a continuous process as an in-line system.
  • the pressure conditions necessary for creating a plasma discharge within the chamber are maintained using high volume pumps, as is conventional for example in a device with a "whistling leak".
  • high volume pumps as is conventional for example in a device with a "whistling leak”.
  • a second aspect of the present invention provides use of a polymer coating obtained by plasma polymerisation on a wool containing fibre, yarn, sliver, fabric or garment made from said fibre or yarn to reduce shrinkage due to felting during
  • a third aspect of the present invention provides a wool
  • a fifth aspect of the present invention provides use of a polymer coating obtained by plasma polymerisation on a wool containing fibre, yarn, sliver, fabric or garment made from said fibre or yarn as a water and/or oil repellent coating which does not require post laundering refreshing.
  • Preferred features of the second, third, fourth and fifth aspects of the invention may be as described above in connection with the first aspect.
  • any feature disclosed herein may be replaced by an alternative feature serving the same or a similar purpose.
  • the resulting coated fabrics were then tested for water and oil repellency, fluorine content and mechanical properties .
  • the fabrics samples tested were untreated wool, Chlorine- Hercosett treated wool and polyester/wool blend fabrics, containing hollow and solid polyester filaments. These samples were treated with "traditional" fluorocarbon technology and with a plasma polymerisation system. The resulting coated samples were then evaluated for liquid repellency after washing, dry cleaning and flat abrasion and the results of the different fluorocarbon coating compared.
  • the three different wool containing fabrics were: 100% wool botany serge (190g/m 2 , supplied by Whaleys, Bradford), plain weave chlorine-Hercosett treated wool (100% wool, 210 g/m 2 ) supplied by Bulmer & Lumb, Bradford and undyed wool/polyester (60/4) blend fabrics (yarn count 60/2, 160 g/m 2 ) also supplied by Bulmer & Lumb, Bradford.
  • the SDC ECE phosphate-based reference detergent without optical brightening agents, was used during the wash fastness tests. It was used as the washing powder addition because it is the standard detergent in the ISO C06 wash fastness tests to simulate domestic laundering.
  • the wool fabrics Prior to finishing, the wool fabrics were washed with an aqueous non-ionic detergent solution to remove any possible impurities which could potentially interfere with the subsequent surface treatment; and then air dried.
  • the "traditional" fluorocarbons were applied to the samples by the following method. Fabric samples were treated using a pad- dry-cure method with either 50g/l Oleophobol SL-A or 50g/l Fluorepel OWS . The pad bath was set at pH 6-7 and the wet pickup was 70%. The padded fabrics were dried at 100°C for 2 minutes (100% wool fabrics) or 1 minute (blend fabrics), and then cured for 5 minutes at 150°C or 1 minute at 170°C for the wool and blend fabrics, respectively.
  • the plasma polymerisation coating was applied by the following method.
  • the plasma polymerization experiments were performed in an inductively coupled glow discharge reactor with a base pressure of 6.13 ⁇ 10 ⁇ 3 mbar, a leak rate of better than 6 ⁇ 10 ⁇ 9 mol s -1 and a monomer flow rate 4mg/min or 3.2 mol s '1 .
  • This was connected to a two stage Edwards rotary pump via a liquid nitrogen cold trap, a thermocouple pressure gauge, and a monomer tube containing the 1H, 1H, 2H, 2H-heptadecafluorodecyl acrylate monomer. All connections were grease free.
  • An L-C matching unit was used to minimize the standing wave ratio (SWR) of the transmitted power between a 13.56 MHz radio frequency (RF) generator and the electrical discharge.
  • the RF source was triggered by a signal generator, and an oscilloscope was used to monitor the pulse width and amplitude.
  • the substrate to be coated was placed into the centre of the reactor, followed by evacuation back down to the base pressure.
  • the fluoro-monomer vapour was then introduced at a constant pressure of -0.2 mbar and allowed to purge through the system for 5 minute, followed by ignition of the glow discharge.
  • the pressure on the reactor outlet was found to be steady, which is consistent with sufficient monomer flow rate.
  • Deposition was terminated after enough time to form a film, based on the previous trials, on the substrates surface.
  • the monomer vapour was allowed to continue to pass over the substrate for a further 5 minute and subsequently the plasma chamber was evacuated back down to the base pressure and then vented to the atmosphere.
  • the optimum pulsing conditions were determined using factorial experimental design, followed by simplex optimization.
  • the abrasion resistance of finished fabrics was measured according to BS 12947-2: 1999, on a Martindale Wear & Abrasion Tester and the repellency properties evaluated after 3,000 rubs.
  • the fabrics were hot-pressed using an Elnapress/SDL with the standard wool temperature setting.
  • a hot press treatment is identified as HP in the results tables.
  • Table 1 indicates the effectiveness of the plasma polymerisation of the fluoro-monomer on the Chlorine Hercosett treated wool fabric in imparting water repellency relative to the traditional wet chemical fluorocarbon applications.
  • the table shows the different results when an argon plasma pre- treatment is applied for 1, 2 or 3 minutes respectively. It is apparent that the argon plasma pre-treatment prior to plasma polymerisation system has introduced much better polymer reorientation behaviour at room temperature, hence not requiring a hot press for restoring the water repellency performance after laundering .
  • Pre-treating the wool with an argon plasma has a beneficial effect in eliminating/reducing the need for a post-heat
  • the oil repellency of the fabric was determined using the AATCC 118-2007 oil repellency test using a series of eight standard hydrocarbon solutions.
  • the oil repellency grade is the highest numbered test liquid which does not wet the fabric surface.
  • Table 2 below shows the results of the 3M Oil Repellency Analysis of Fluorocarbon Treated Chlorine/Hercosett Wool Fabrics.
  • Table 2 indicates the effectiveness of the plasma polymerisation of the fluoro-monomer on the Chlorine Hercosett treated wool fabric in imparting oil repellency relative to the traditional wet chemical fluorocarbon applications.
  • ToF-SIMS secondary ion mass spectrometry
  • Hercosett process removes the covalently bound hydrophilic 18- methyleicosanoic acid (18-MEA) from the epicuticle) .
  • the charge neutraliser flood gun provided a constant stream of electrons in order to neutralize the charge build up. Binding energy values were calculated relative to the C(ls) photoelectron peak at 285.0 eV.
  • the samples surface elemental composition and atomic ratios were obtained by Casa XPS software and Wagner's sensitivity factors.
  • the XPS (X-ray photoelectron spectroscopy) data of the plasma treated sample indicates obvious incorporation of fluorocarbon into the surface of the fibre with the fluorine content
  • the tensile properties of the fabrics were determined according to the BS 13934-1:1999 test method on an Instron model 5564, with gauge length of 100 mm, crosshead speed of 50mm/min, and each value presented is the average of 10 measurements.
  • the influence of the treatments on the fabric' s mechanical (handle) properties both before and after treatment was
  • the 20x20cm samples were conditioned at 20 ° C and 65% R.H.
  • Table 4 shows the tensile strength of wool fabrics treated with plasma and fluorocarbons, whilst table 5 shows the results for KES-F analysis of the selected mechanical properties of the Chlorine Hercosett treated wool fabrics.
  • the felting shrinkage of the wool fabrics was determined using a Wascator FOM 71P, with a standard 5A wash programme. Fabric shrinkage was determined after each wash cycle by measuring the new fabric area and comparing it with the initial area value. The fabric samples were dry cleaned in accordance with the BS EN ISO 3175:1998 test method, by PPT Company, Ambergate, and their repellency properties were determined after 1 and 3 cycles. The results are shown in table 6.
  • fluoropolymer overlayer is masking the underlying protein or Hercosett polymer.
  • the ToF-SIMS spectra of the PP fabrics also indicate the presence of characteristic perfluoro ions.
  • the Chlorine Hercosett treated wool is machine washable and the PP treatment does not affect this vital performance criteria.
  • the untreated wool fabric shrinks by 63% in area with repeated launderings and the Oleophobol and Fluorepel coatings do not affect this level of felting shrinkage.
  • the fluoropolymer PP treatment significantly reduces the felting shrinkage.
  • the effect of the fluorocarbon treatments on the tensile strength of the fabrics is marginal, while the KES-F analysis of the fabrics indicated the Oleophobol and Fluorepel finishes impart some fabric stiffening, in contrast the PP treatment appears to have a beneficial effect on fabric handle on the blend fabrics.
  • nanoparticles were applied to a wool sample before a
  • the wool sample was 100% wool botany serge (190g/m2) was supplied by Whaleys, Bradford.
  • the ⁇ traditional' fluorochemical used was Oleophobol SL-A 0, Ciba and the shrink proofing polymer Synthapret BAP was supplied by Bayer.
  • H2C CHC02CH2CH2 (DF2) 7CF3) (Fluorochem, 98% purity, further purified using multiple freeze-thaw cycles) was used as the feed monomer in the plasma reactor.
  • the fabric samples were padded with a bath containing 0.3% on weight of fabric, o.w.f., nanoparticles and 5ml/l iso-propanol , at 70% wet pick up.
  • the different sized nanoparticles are shown in table 11.
  • the padded fabrics were dried at 100°C for 2 minutes and then cured for 4 minutes at 140°C.
  • Fabric samples were treated with the ⁇ traditional's
  • Synthapret BAP 24g/l Oleophobol SL-A, 0.3% on weight of fabri o.w.f., nanoparticles and 5ml/l iso-propanol .
  • the pad bath was set at pH6-7, using acetic acid, and the wet pick-up was 70%.
  • the padded fabrics were dried at 100°C for 2 minutes and then cured for 4 minutes at 140°C.
  • the felting shrinkage of the wool fabrics was determined using a Wascoator FOM 71P, with a standard 5A wash programme as
  • Table 12 shows the fabric shrinkage for the wool coated with silica nanoparticles with different
  • the fluoropolymers plasma polymerisation has the beneficial effect in reduction of felting shrinkage.
  • Table 12 shows the effect of silica nanoparticles on felting shrinkage in combination with different treatments.
  • Snowtex OS (4- 57.2 Snowtex OS (4- 20.6 6nm) 6nm)
  • Snowtex 0 (10- 56.2 Snowtex 0 (10- 23.1 20nm) 20nm)
  • Oleophobol 8 0 5 0 7
  • Snowtex OL 0 0 0 0 0 0 0 0
  • nanoparticles have relatively little effect in improving the repellency performance. Similarly the effect of incorporating the nanoparticles into the fluoropolymers plasma polymerisation system is marginal except for the samples where the plasma polymerisation is directly onto nanoparticle along pre-treated fabric (highlighted in tables) .
  • the fabric colour was measured using a Datacolor Reflectance Spectrophotometer.
  • the samples were triple folded and an average of four valued used to provide the mean. The results are illustrated in tables 17 and 18.
  • Snowtex OS (4- -10.9 -0.1 26.6 -0.3 6nm)
  • Snowtex 0 (10- -10.9 -0.2 26.6 -0.3 20nm)
  • Snowtex OL 40- -6, 4 4.3 24.1 -2.8 50nm
  • MP-1040 (lOOnm) -4.7 6.0 23.3 -3.5
  • Snowtex OS (4-6nm) -11.9 -1.5 27.2 0.7
  • Snowtex 0 (10- -10.6 -0.2 26.6 0.1 20nm)
  • Snowtex OL (40- -9,8 0.6 26.2 -0.3 50nm)
  • Snowtex OL (40- 0.1084 0.36 1.10
  • the effect of the nanoparticles on the mechanical properties of the treated fabric is variable, If applied alone or alone followed by a plasma polymerisation process the 2HG5 value (the indicator of interyarn friction and softness) increases;
  • nanoparticles on fabric handle is variable depending on the application condition. However, where the nanoparticles are relatively “exposed” it appears the surface protrusions increase interyarn friction and harshen fabric handle. SEM analysis indicated the distribution of the nanoparticles is uneven, either located at the scale edges or within the fluoropolymers film. Argon plasma pre-treatment improves the distribution of the nanoparticles on the wool fabric.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Physics & Mathematics (AREA)
  • Plasma & Fusion (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention a trait à un procédé permettant de traiter la laine sous forme de fibre, de fil, de ruban, de tissu ou de vêtement. Un enduit de polymère est appliqué par polymérisation plasma afin d'empêcher tout rétrécissement dû au feutrage découlant du blanchissage. Le procédé peut inclure une étape de prétraitement, par exemple l'application d'un plasma continu de gaz inerte, l'application de nanoparticules sur la surface de fibre ou l'enduction de la surface de fibre au moyen d'un polymère.
PCT/GB2010/051619 2009-11-25 2010-09-28 Produit et procédé innovant WO2011064562A2 (fr)

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CA2780700A CA2780700A1 (fr) 2009-11-25 2010-09-28 Produit et procede innovant
US13/512,064 US20130117978A1 (en) 2009-11-25 2010-09-28 Reducing shrinkage of wool and wool blend fabrics due to felting
JP2012540495A JP2013512352A (ja) 2009-11-25 2010-09-28 新規製品及び方法
CN2010800624166A CN102844490A (zh) 2009-11-25 2010-09-28 通过等离子体聚合反应使羊毛防缩的方法
AU2010322855A AU2010322855B2 (en) 2009-11-25 2010-09-28 Method to shrinkproof wool by plasma polymerization
EP10769045A EP2510147A2 (fr) 2009-11-25 2010-09-28 Procede pour effectuer un traitement anti-retrecissant de la laine par polymerisation en plasma
NZ600440A NZ600440A (en) 2009-11-25 2010-09-28 Method to shrinkproof wool by plasma polymerization
IL219873A IL219873A0 (en) 2009-11-25 2012-05-17 Novel product and method

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GB201316115D0 (en) * 2013-09-10 2013-10-23 Europlasma Nv Surface Coatings
JP6423347B2 (ja) * 2012-10-09 2018-11-14 ユーロブラズマ エンヴェー 表面コーティング
US9002041B2 (en) * 2013-05-14 2015-04-07 Logitech Europe S.A. Method and apparatus for improved acoustic transparency
DE102013016587A1 (de) * 2013-10-08 2015-04-09 Martin-Luther-Universität Halle-Wittenberg, Körperschaft des öffentlichen Rechts Verfahren zur Herstellung von nanopartikel-dotierten Pflanzenfasern, insbesondere Baumwollfasern, zur Herstellung von intelligenten Textilien unter Verwendung eines nachhaltigen, automatisierten hydroponischen Systems
EP3722500A1 (fr) 2013-12-13 2020-10-14 The North Face Apparel Corp. Traitements par plasma pour la coloration de textiles
CN104594020A (zh) * 2015-02-09 2015-05-06 苏州陈恒织造有限公司 一种山羊绒纱线防缩工艺
CN105544181B (zh) * 2015-12-30 2017-08-25 江阴市长泾花园毛纺织有限公司 一种亲水防缩双面呢
EP3915343A1 (fr) * 2019-01-25 2021-12-01 Terraplasma GmbH Agencement d'électrodes et source de plasma pour générer un plasma non thermique, ainsi que procédé pour faire fonctionner une source de plasma
JP2021065267A (ja) * 2019-10-18 2021-04-30 テックワン株式会社 使用によって傘のシートの撥水性が低下したのを回復させる方法

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US20130117978A1 (en) 2013-05-16
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AU2010322855A1 (en) 2012-06-21
KR20120081635A (ko) 2012-07-19
IL219873A0 (en) 2012-07-31
WO2011064562A8 (fr) 2011-11-10
GB2475685A (en) 2011-06-01
NZ600440A (en) 2014-06-27
JP2013512352A (ja) 2013-04-11
EP2510147A2 (fr) 2012-10-17
AU2010322855B2 (en) 2015-01-29
CA2780700A1 (fr) 2011-06-03

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