EP2222829A1 - Wirkstoff für textilbehandlung - Google Patents

Wirkstoff für textilbehandlung

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Publication number
EP2222829A1
EP2222829A1 EP08865723A EP08865723A EP2222829A1 EP 2222829 A1 EP2222829 A1 EP 2222829A1 EP 08865723 A EP08865723 A EP 08865723A EP 08865723 A EP08865723 A EP 08865723A EP 2222829 A1 EP2222829 A1 EP 2222829A1
Authority
EP
European Patent Office
Prior art keywords
photo
preferred
hydrophobic
fabric
derivative
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP08865723A
Other languages
English (en)
French (fr)
Other versions
EP2222829B1 (de
Inventor
Mansur Sultan Mohammadi
Kenneth Stuart Lee
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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 filed Critical Unilever PLC
Priority to PL08865723T priority Critical patent/PL2222829T3/pl
Publication of EP2222829A1 publication Critical patent/EP2222829A1/de
Application granted granted Critical
Publication of EP2222829B1 publication Critical patent/EP2222829B1/de
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C11D3/16—Organic compounds
    • C11D3/18—Hydrocarbons
    • C11D3/188—Terpenes
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/12—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
    • D06L1/20—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents combined with mechanical means
    • 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
    • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
    • 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
    • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • D06M13/03—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons with unsaturated hydrocarbons, e.g. alkenes, or alkynes
    • 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
    • D06M13/10—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 oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/13—Unsaturated aldehydes, e.g. acrolein; Unsaturated ketones; Ketenes ; Diketenes
    • 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
    • D06M13/10—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 oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • 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
    • D06M13/10—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 oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties

Definitions

  • the present invention relates to the use of a hydrophobic/hydrophilic material in a laundry treatment composition. More specifically, the present invention relates to the use of a HH material in a laundry treatment composition to increase comfort of laundered fabrics.
  • the uncomfortable feel of clothes associated with perspiration can take one of two forms depending on the level of sweat production. Under conditions of high sweat production, clothes can become saturated with sweat. Damp areas of clothing then contact the skin causing discomfort through local cooling and cling.
  • the textile literature identifies a high humidity level in the space between the skin and the first layer of clothing as one of the key drivers of discomfort under ambient, low exercise conditions.
  • discomfort can arise from the build up of liquid water on the inside surface of apparel textiles.
  • a known approach to this problem is to increase the rate of liquid water transport through textile by increasing the rate of wicking or wetting. This is achieved by decreasing the contact angle of water on the fibre surface.
  • This approach has the disadvantage of also increasing the total amount of water held in the textile. This leads to increased thermal conductivity and increased cling when these areas touch the skin. Both of these effects increase the discomfort experienced in wear.
  • Zinc Oxide Zinc Oxide
  • TiO 2 Titanium Oxide
  • US2005/0186871 Al discloses a gas permeable apparatus comprising a structure including a plurality of surfaces, at least another of the surfaces comprising electrets, at least one light source for exposing the at least one of the surfaces comprising the photocatalyst to light photons sufficient to activate the photocatalyst, the structure allowing for filtering particulates, wicking liquids, disinfecting, and deodarizing the surfaces.
  • Photocatalysts such as Ti ⁇ 2 are incorporated into the surfaces of apparel products such as goggles to decompose and oxidize absorbed chemicals on the photocatalyst surfaces with absorption of light with sufficient energy to generate and electron hole pair in the photocatalyst .
  • the electron hole pair leads to decomposition of surface contact with water and subsequent reactive chemicals on the surface of the photocatalysts .
  • the coated surfaces also can function as air filters, air vents, wicking surfaces, protective covers, layers, over underlying materials, and act as ultraviolet light protective filters for the underlying materials and body.
  • WO2008/058831 discloses a fabric softening composition
  • a fabric softening composition comprising a fabric softening compound and from 5 to 50 % by weight, preferably 5 to 25 % by weight of the composition of a material (HH material) capable of changing its hydrophobic/hydrophilic properties in response to an activation step.
  • HH material material
  • an HH material in a fabric softener composition, comprising a fabric softening compound, to increase comfort of fabric, wherein the HH material is capable of changing its hydrophobic/hydrophilic properties in response to an activation step, and wherein the HH material is a terpene having the general formula :- (C 5 Hg) n where n is from 3 to 8.
  • the idea of the invention is to reduce the level of water held in the region of the textile next to the skin, at the same time as facilitating the movement of water through the textile, in order to increase comfort of the fabric. This is achieved by creating different surface properties on fibres in different regions of the textile (either different regions of the garment, or different sides of the textile) . Areas of the textile which are close to the skin are made hydrophobic, while the areas of the textile which are away from the skin are made hydrophilic. In this manner it is possible to increase water transport without increasing the water holding properties of the textile. Increasing water transport while also decreasing the amount of water held at the surface of the textile closest to the skin provides a beneficial effect. It is possible to maintain comfort for the wearer under conditions of low sweat production i.e. under low exercise conditions, with warm climate etc, or at least delay the outset of discomfort when the wearer is exposed to such conditions.
  • the key to this approach is to generate different local fibre properties following uniform treatment of the textile with a laundry product.
  • a laundry product By depositing the HH material onto the textile from the laundry treatment, areas which are close to the skin can be made hydrophobic, whereas areas of textile away from the skin may be rendered hydrophilic by an activation step.
  • the activation step uses local environmental conditions.
  • the HH material is photosensitive and the outside of the garment is exposed to light, particularly UV light, and is rendered hydrophilic, whilst the inside of the garment close to the skin and therefore shielded from the sunlight remains hydrophobic.
  • Comfort includes the increase in moisture transport away from the skin and the reduction of humidity in any space between the skin and first layer of clothing and within the clothing immediately adjacent the skin .
  • any material which can be deposited on a fabric from a rinse conditioner which can "switch" properties from hydrophobic to hydrophilic or visa versa upon exposure to certain conditions may be employed in the invention.
  • the activation step causing the switch in properties may be based upon photosensitivity, pH change, temperature change, heat flow, change in ionic strength, enzymatic activity etc.
  • the most convenient activation step is based upon photosensitivity, particularly UV light, since it is readily possible to expose the outside of a garment to sunlight, during wear and or drying, whilst shielding the inside of the garment .
  • Preferred HH materials are those that undergo photo-fission to generate more hydrophilic fragments from a hydrophobic precursor.
  • Aliphatic carbonyl compounds which undergo Norrish Type II photoreaction
  • Other suitable photosensitive materials include those which undergo:
  • the HH materials are generally deposited to apply from 0.2 to 1 %, preferably 0.2 to 0.5 % by weight of the fabric after drying.
  • the HH materials are generally present in an amount of from 0.5 to 15 %, preferably 1 to 10 % in the fabric softening composition.
  • HH materials upon exposure to light.
  • the rate of the photo- fission can be controlled by the presence of photo-bleaches.
  • a HH material is any chemical species, which is a precursor to more hydrophilic species (or a further precursor thereof) upon exposure to light in the presence or absence of an active photo-bleach.
  • Preferred HH materials contain at least one, non-aromatic, C-C double-bond, more preferably at least two C-C double- bonds.
  • the HH material is a lipid.
  • Preferred lipids contain mono- or di-unsaturated fatty acids (or their esters) .
  • HH materials comprise the structure (I) below:
  • Ri and R 2 are selected such that fragmentation of the molecule following exposure to the photo-bleach leads to the production of hydrophilic compounds .
  • HH materials comprises food lipids.
  • Food lipids typically contain structural units with pronounced hydrophobicity .
  • the majority of lipids are derived from fatty acids.
  • the fatty acids are predominantly present as esters and include mono-, di-, triacyl glycerols, phospholipids, glycolipids, diol lipids, waxes, sterol esters and tocopherols.
  • Plant lipids have the necessary complement of antioxidants to prevent their oxidation. During the isolation of oils from plants some of these antioxidants are reduced but sufficient level remains. These antioxidants, including vitamins A and its several forms (retinol, retinal and retinoic acid and its carotenoid precursors, provitamin A) and vitamin E can be a added to HH material to control the rate of photo-fragmentation.
  • Preferred food lipids include amaranth oil, olive oil, palm oil, canola oil, sunflower seed oil, wheat germ oil, almond oil, coconut oil, grape seed oil, rapeseed oil, castor oil, corn oil, cottonseed oil, safflower oil, evening primrose oil, groundnut oil, poppy seed oil, palm, palm kernel oil, rice bran oil, sesame oil, soybean oil, and jojoba oil.
  • Preferred food lipids also include oils and fats of animal source including squalene (also present in olive oil and wheat germ oil) butter, and ghee. To avoid allergic reaction, certain nut oils (peanut oil, for example) are less preferred.
  • a particularly preferred class of HH materials are the terpenes .
  • Terpenes are derived from units of isoprene, which has the molecular formula CsHg.
  • the basic molecular formulae of terpenes are given by the formula:- ( C 5 Hg ) n
  • n is the number of linked isoprene units.
  • the isoprene units may be linked together "head to tail” to form linear chains or they may be arranged to form rings.
  • Those suitable for use in the present invention are preferably linear .
  • the number of carbon to carbon double bonds is from 3 to 8, preferably 6.
  • Squalene is a triterpene, has 6 double bounds and a linear structure .
  • Preferred oils may be selected from the group consisting of soy oil, grapeseed oil, castor oil, hexadecane and squalene, preferably squalene.
  • Another class of preferred lipids are the oily sugar esters described below under fabric softening materials.
  • the most preferred HH materials contain at least 20 wt% of a compound which comprises the moiety
  • Rl and R2 are organic groups containing carbon, hydrogen and oxygen.
  • a preferred example is linoleic acid.
  • Particularly preferred fatty acid containing lipids contain 10 wt% or less of moieties containing three double bonds, (such as linolenic acid) . Also the most preferred lipids contain less than 15 wt% saturated acids and less than 15 wt% of acids with less than 14 carbon atoms. Within these preferred limits branched-chain and hydroxyl acid moieties are included
  • Most preferred oils exclude those of high linolenic content (preferred ⁇ 10%) , such as hemp oil ( ⁇ 25%wt linolenic acid) , and oils of nut origin.
  • a laundry care composition comprising a photo-bleach and a HH material.
  • a "photo-bleach” is any chemical species which forms a reactive bleaching species on exposure to sunlight, and preferably is not permanently consumed in the reaction.
  • Preferred photo- bleaches include singlet oxygen photo-bleaches and radical photo-bleaches. Suitable photo-bleaches are described in more detail below.
  • Preferred levels of photo-bleach present in the composition are from 0 to 0.01 wt% preferably 0.00005 to 0.05%.
  • Some of the photo-bleaches impart colour to the fabric. To give the clothes an appealing white hue, it is preferred if blue or violet shading dyes are used in combination with the photo-bleaches. In the alternative a combination of photo- bleaches is used to generate a white hue.
  • Preferred dyes are as described in WO2005/003274 (Unilever) and WO2005/003277 (Unilever) .
  • Particularly preferred shading dyes are bis azo direct dyes, particularly those of the direct violet 9, 35 and 99 type and acid azine dyes such as acid violet 50 and acid blue 98.
  • Alternative shading dyes are described below. Dyes can sometimes act as a photo- sentisiser .
  • photo-bleaches suitable for use in the present invention include singlet oxygen photo-bleaches and radical photo-bleaches.
  • PB Singlet oxygen photo-bleaches
  • the photo-bleach molecule absorbs light and attains an electronical excited state, PB*.
  • This electronically excited state is quenched by triplet oxygen, 3 ⁇ 2, in the surroundings to form singlet 1 O ⁇ .
  • Singlet oxygen is a highly reactive bleach.
  • Suitable singlet oxygen photo-bleaches may be selected from, water soluble phthalocyanine compounds, particularly metallated phthalocyanine compounds where the metal is Zn or Al-Zl where Zl is a halide, sulphate, nitrate, carboxylate, alkanolate or hydroxyl ion.
  • the phthalocyanin has 1-4 SO3X groups covalently bonded to it where X is an alkali metal or ammonium ion.
  • X alkali metal or ammonium ion
  • Xanthene type dyes are preferred, particularly based on the structure :
  • the dye may be substituted by halogens and other elements/groups.
  • Particularly preferred examples are Food Red 14 (Acid Red 51), Rose Bengal, Phloxin B and Eosin Y.
  • Other singlet oxygen producing compounds include chlorophyll, coumarin, porphyrins, myoglobin, riboflavin, bilirubin, and methylene blue.
  • the singlet oxygen photo-bleaches generally impart some colour to the fabric.
  • blue or violet photo-bleach dyes are used in combination with the shading dyes as described in WO2005/003274 (Unilever) and WO2005/003277 (Unilever) .
  • Particularly preferred shading dyes are bis azo direct dyes of the direct violet 9, 35 and 99 type and acid azine dyes such as acid violet 50 and acid blue 98.
  • Radical photo-bleaches are well known chemicals in the plastics and curing industry. These application have been widely discussed in the literature see e.g. H. F. Gruber Prog. Polym. Sci. 17 (1992), 953-1044 and references therein. They are organic chemicals which on exposure to light react to form neutral radicals that may initiate the polymerization of alkenes. Recently they have been found to be effective laundry photo-bleaches: UK patent application 9917451.8 teaches their use from main wash detergent powders and liquids, where the photo-initiators are intimately mixed into the powder or liquids. Radical photo-bleaches are molecules that absorb light (typically 290-400nm) to produce organic carbon-centered radicals . Radical photo-bleaches may function by intermolecular hydrogen abstraction or by intramolecular alpha or beta bond cleavage .
  • Suitable radical photo-bleaches may be selected from quinones, ketones, aldehydes, and phosphine oxides.
  • the maximum extinction coefficient is between 290 and 400 nm (measured in ethanol) is greater 10, more preferably greater than 100 mol "1 L cm “1 .
  • a particularly preferred class of radical photo-bleaches are based on the structure:
  • Rl may be H, OH, Oalkyl preferably methoxy or ethoxy
  • R2 may be H
  • R3 may be H, Cl- C9 alkyl
  • Rl, R2 and R3 are hydrogen
  • the phenyl ring, A may be substitute at the 3,4 and 5 position by:
  • Preferred examples of this type are acetophenone, 4 methyl acetophenone, 4 methoxy acetophenone.
  • Benzophenone and vitamin K3 are also preferred radical photo-bleach.
  • Suitable bond cleavage radical photo initiators may be selected from the following groups:
  • alpha amino ketones particularly those containing a benzoyl moiety, otherwise called alpha-amino acetophenones, for example 2-methyl 1- [4-phenyl] -2- morpholinopropan-1-one (Irgacure 907, trade mark), (2- benzyl-2-dimethyl amino-1- (4-morpholinophenyl) -butan-1- one (Irgacure 369, trade mark);
  • alphahydroxy ketones particularly alpha-hydroxy acetophenones, eg (1- [4- (2-hydroxyethoxy) -phenyl] -2- hydroxy-2-methyl-l-propan-l-one) (Irgacure 2959, trade mark), 1-hydroxy-cyclohexyl-phenyl-ketone (Irgacure 184, trade mark) ;
  • phosphorus-containing photoinitiators including monoacyl and bisacyl phosphine oxide and sulphides, for example 2-4-6- (trimethylbenzoyl) diphenyl-phosphine oxide, bis (2,4, 6-trimethylbenzoyl) -phenyl-phosphine oxide (Irgacure 819, trade mark), (2,4,6- trimethylbenzoyl) phenyl phosphinic acid ethyl ester (Lucerin TPO-L (trade mark) ex BASF) ;
  • monoacyl and bisacyl phosphine oxide and sulphides for example 2-4-6- (trimethylbenzoyl) diphenyl-phosphine oxide, bis (2,4, 6-trimethylbenzoyl) -phenyl-phosphine oxide (Irgacure 819, trade mark), (2,4,6- trimethylbenzoyl) phenyl phosphinic acid ethyl ester (Lucerin TPO-L (trade
  • WO 9607662 (treacly phosphate oxides), US 5399782 (phosphine sulphides), US 5410060, EP-A-57474, EP-A-73413 (phosphine oxides), EP-A-088050, EP-A-0117233, EP-A-0138754, EP-A- 0446175 and US 4559371.
  • Radical photo-bleaches are discussed in general in A. F. Cunningham, V. Desorby, K. Dietliker, R. Husler and D. G. Leppard, Chemia 48 (1994) 423-426. They are discussed in H. F. Gruber Prog. Polym. Sci. 17(1992) 953-1044.
  • the photo-bleach will typically have a cleaning function as well as reacting with the HH material.
  • Inorganic photo-bleaches including titanium dioxide are also preferred because they are HH material in their own right .
  • the fabric softening compound which is different from the HH material. Suitable fabric softening compounds are described below.
  • the oily sugar derivative is a liquid or soft solid derivative of a cyclic polyol or of a reduced saccharide, said derivative resulting from 35 to 100% of the hydroxyl groups in said polyol or in said saccharide being esterified or etherified.
  • the derivative has two or more ester or ether groups independently attached to a C8-C22 alkyl or alkenyl chain.
  • oily sugar derivatives of the invention are also referred to herein as "derivative-CP” and “derivative-RS” dependent upon whether the derivative is a product derived from a cyclic polyol or from a reduced saccharide starting material respectively.
  • the derivative-CP and derivative-RS contain 35% by weight tri or higher esters, e.g. at least 40%.
  • 35 to 85% most preferably 40 to 80%, even more preferably 45 to 75%, such as 45 to 70% of the hydroxyl groups in said cyclic polyol or in said reduced saccharide are esterified or etherified to produce the derivative-CP and derivative-RS respectively.
  • the tetra, penta etc prefixes only indicate the average degrees of esterification or etherification .
  • the compounds exist as a mixture of materials ranging from the monoester to the fully esterified ester. It is the average degree of esterification as determined by weight that is referred to herein.
  • the derivative-CP and derivative-RS used do not have substantial crystalline character at 2O 0 C. Instead they are preferably in a liquid or soft solid state, as hereinbelow defined, at 2O 0 C.
  • the starting cyclic polyol or reduced saccharide material is esterified or etherified with C8-C22 alkyl or alkenyl chains to the appropriate extent of esterication or etherification so that the derivatives are in the requisite liquid or soft solid state.
  • These chains may contain unsaturation, branching or mixed chain lengths .
  • the derivative-CP or derivative-RS has 3 or more, preferably 4 or more, for example 3 to 8, e.g. 3 to 5, ester or ether groups or mixtures thereof. It is preferred if two or more of the ester or ether groups of the derivative-CP and derivative-RS are independently of one another attached to a Cs to C22 alkyl or alkenyl chain. The alkyl or alkenyl groups may be branched or linear carbon chains.
  • the derivative-CPs are preferred for use as the oily sugar derivative. Inositol is a preferred cyclic polyol, and Inositol derivatives are especially preferred.
  • derivative-CP and derivative-RS encompass all ether or ester derivatives of all forms of saccharides, which fall into the above definition, and are especially preferred for use.
  • preferred saccharides for the derivative-CP and derivative-RS to be derived from are monosaccharides and disaccharides .
  • Examples of monosaccharides include xylose, arabinose, galactose, fructose, sorbose and glucose. Glucose is especially preferred.
  • An example of a reduced saccharide is sorbitan.
  • Examples of disaccharides include maltose, lactose, cellobiose and sucrose. Sucrose is especially preferred.
  • the derivative-CP is based on a disaccharide it is preferred if the disaccharide has 3 or more ester or ether groups attached to it. Examples include sucrose tri, tetra and penta esters.
  • each ring of the derivative-CP has one ether group, preferably at the Ci position.
  • Suitable examples of such compounds include methyl glucose derivatives.
  • Suitable derivative-CPs include esters of alkyl (poly) glucosides, in particular alkyl glucoside esters having a degree of polymerisation from 1 to 2.
  • the HLB of the derivative-CP and derivative-RS is typically between 1 and 3.
  • the derivative-CP and derivative-RS may have branched or linear alkyl or alkenyl chains (of varying degrees of branching), mixed chain lengths and/or unsaturation . Those having unsaturated and/or mixed alkyl chain lengths are preferred.
  • One or more of the alkyl or alkenyl chains may contain at least one unsaturated bond.
  • predominantly unsaturated fatty chains may be attached to the ester/ether groups, e.g. those attached may be derived from rape oil, cotton seed oil, soybean oil, oleic, tallow, palmitoleic, linoleic, erucic or other sources of unsaturated vegetable fatty acids.
  • the alkyl or alkenyl chains of the derivative-CP and derivative-RS are preferably predominantly unsaturated, for example sucrose tetratallowate, sucrose tetrarapeate, sucrose tetraoleate, sucrose tetraesters of soybean oil or cotton seed oil, cellobiose tetraoleate, sucrose trioleate, sucrose triapeate, sucrose pentaoleate, sucrose pentarapeate, sucrose hexaoleate, sucrose hexarapeate, sucrose triesters, pentaesters and hexaesters of soybean oil or cotton seed oil, glucose trioleate, glucose tetraoleate, xylose trioleate, or sucrose tetra-, tri-, penta- or hexaesters with any mixture of predominantly unsaturated fatty acid chains.
  • Unsaturation as mentioned earlier can help fragmentation of molecules into more hydrophilic components by photoreaction .
  • the softener
  • derivative-CPs and derivative- RSs may be based on alkyl or alkenyl chains derived from polyunsaturated fatty acid sources, e.g. sucrose tetralinoleate . It is preferred that most, if not all, of the polyunsaturation has been removed by partial hydrogenation if such polyunsaturated fatty acid chains are used.
  • liquid derivative-CPs and derivative-RSs are any of those mentioned in the above three paragraphs but where the polyunsaturation has been removed through partial hydrogenation.
  • polyunsaturation with limited ⁇ 10% linolenic fatty acids is acceptable .
  • a fatty acid mixture (to react with the starting cyclic polyol or reduced saccharide) which comprises a mixture of tallow fatty acid and oleyl fatty acid in a weight ratio of 10:90 to 90:10, more preferably 25:75 to 75:25, most preferably 30:70 to 70:30.
  • a fatty acid mixture comprising a mixture of tallow fatty acid and oleyl fatty acid in a weight ratio of 60:40 to 40:60 is most preferred.
  • fatty acid mixtures comprising a weight ratio of approximately 50 wt% tallow chains and 50wt% oleyl chains. It is especially preferred that the fatty acid mixture consists only of a mixture of tallow fatty acid and oleyl fatty acid.
  • the chains Preferably 40% or more of the chains contain an unsaturated bond, more preferably 50% or more, most preferably 60% or more e.g. 65% to 95%.
  • oilsy sugar derivatives suitable for use in the compositions include sucrose pentalaurate, sucrose pentaerucate and sucrose tetraerucate .
  • suitable materials include some of the Ryoto series available from Mitsubishi Kagaku Foods Corporation.
  • Suitable oily sugar derivatives are those disclosed in our recent WO2006076952 (Al) such as Emanon SCR-PK (ex KAO) , which is a palm kernel derived SPE containing mainly C12-C14 with about 20% C18 mono unsaturatation and SPE-THSBO (ex Clariant) , which is derived from touch hardened soy bean oil, having mainly C16-C18 chains with about 80% mono and di unsaturation .
  • Emanon SCR-PK ex KAO
  • SPE-THSBO Clariant
  • the average degree of esterification of the above preferred SPEs is between 4.2-4.7.
  • the liquid or soft solid derivative-CPs and derivative-RSs are characterised as materials having a solid: liquid ratio of between 50:50 and 0:100 at 20 0 C as determined by T 2 relaxation time NMR, preferably between 43:57 and 0:100, most preferably between 40:60 and 0:100, such as, 20:80 and 0:100.
  • the T 2 NMR relaxation time is commonly used for characterising solid: liquid ratios in soft solid products such as fats and margarines.
  • any component of the NMR signal with a T2 of less than 100 microsecond is considered to be a solid component and any component with T2 greater than 100 microseconds is considered to be a liquid component.
  • the liquid or soft solid derivative-CPE and derivative-RSE can be prepared by a variety of methods well known to those skilled in the art. These methods include acylation of the cyclic polyol or of a reduced saccharide with an acid chloride; trans-esterification of the cyclic polyol or of a reduced saccharide material with short chain fatty acid esters in the presence of a basic catalyst (e.g. KOH); acylation of the cyclic polyol or of a reduced saccharide with an acid anhydride, and, acylation of the cyclic polyol or of a reduced saccharide with a fatty acid. Typical preparations of these materials are disclosed in US 4 386 213 and AU 14416/88 (Procter and Gamble) .
  • compositions preferably comprise between 0.5%-30% wt of the oily sugar derivatives, more preferably 1-20% wt, most preferably 1.5- 20% wt, e.g. 3-15% wt %, based on the total weight of the composition.
  • the preferred cationic fabric softening compound (s) are those having two or more alkyl or alkenyl chains each having an average chain length equal to, or greater than Cs, especially C12-28 alkyl or alkenyl chains connected to a nitrogen atom.
  • the alkyl or alkenyl groups are preferably connected via at least one ester link, more preferably via two or more ester linkages.
  • the cationic fabric softening compounds may be ester-linked quaternary ammonium fabric softening compounds or non-ester linked quaternary ammonium fabric softening compounds.
  • the ester-linked quaternary ammonium fabric softening compounds are herein referred to as "the ester-softening compound”.
  • the non-ester linked quaternary ammonium fabric softening compounds are herein referred to as "the non-ester softening compound” .
  • Especially suitable compounds have two or more alkyl or alkenyl chains each having an average chain length equal to, or greater than Ci 4 , more preferably, equal to or greater C16. Most preferably at least 50% of the total number of alkyl or alkenyl chains have a chain length equal to, or greater than C18 •
  • ester- softening compound is biologically degradable. It is also preferred if the alkyl or alkenyl chains of the ester- softening compound are predominantly linear.
  • ester-softening compound is a quaternary ammonium material represented by formula (I) : TR Z
  • T is -O-C- or -C-O-; each R 1 group is independently selected from C 1 - 4 , alkyl or hydroxyalkyl or C 2 - 4 alkenyl groups; and wherein each R 2 group is independently selected from C8- 2 8 alkyl or alkenyl groups,
  • X ⁇ is any suitable anion including a halide, acetate or lower alkosulphate ion, such as chloride or methosulphate, n is O or an integer from 1-5, and m is from 1-5.
  • Preferred materials of this class such as 1,2 bis [hardened tallowoyloxy] -3- trimethylammonium propane chloride and their method 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 3-trimethylammonium propane chloride.
  • a second preferred type of ester-softening compound is represented by the formula (II) : R 1
  • T, R 1 , R 2 , n, and X are as defined above.
  • di (tallowoyloxyethyl) dimethyl ammonium chloride and methyl bis-[ethyl (tallowoyl) ]- 2-hydroxyethyl ammonium methyl sulphate are especially preferred.
  • the tallow chains in these compounds may be hardened and may even be fully unsaturated, i.e. preferred compounds also include di (hardened tallowoyloxy ethyl) dimethyl ammonium chloride and methyl bis- [ethyl (hardened tallowoyl) ] -2- hydroxyethyl ammonium methyl sulphate.
  • Commercially available compounds include those in the Tetranyl range (ex Kao) and Stepantex range (ex Stepan) .
  • derivatives of the above formula where one or more of the (CH 2 ) n chain (s) has at least one pendent alkyl chain e.g. a methyl chain are also suitable.
  • examples include the cationic quaternary ammonium compounds described in WO 99/35223 and WO 99/35120 (Witco) .
  • a third preferred type of ester-softening compound is a quaternary ammonium material represented by the formula (III) : O O R"
  • A is an (m+n) valent radical remaining after the removal of (m+n) hydroxy groups from an aliphatic polyol having p hydroxy groups and an atomic ratio of carbon to oxygen in the range of 1.0 to 3.0 and up to 2 groups per hydroxy group selected from ethylene oxide and propylene oxide
  • m is 0 or an integer from 1 to p-n
  • n is an integer from 1 to p-m
  • p is an integer of at least 2
  • B is an alkylene or alkylidene group containing 1 to 4 carbon atoms
  • R 3 , R 4 , R 5 and R 6 are, independently from each other, straight or branched chain C1-C48 alkyl or alkenyl groups, optionally with substitution by one or more functional groups and/or interruption by at most 10 ethylene oxide and/or propylene oxide groups, or by at most two functional groups selected from;
  • R 4 and R 5 may form a ring system containing 5 or 6 atoms in the ring, with the proviso that the average compound either has at least one R group having 22-48 carbon atoms, or at least two R groups having 16-20 carbon atoms, or at least three R groups having 10-14 carbon atoms.
  • Preferred compounds of this type are described in EP 638 639 (Akzo) .
  • the non-ester softening compound preferably has the alkyl or alkenyl chain lengths referred to above (in respect of the non-ester softening compounds) .
  • non-ester softening compound is a quaternary ammonium material represented by formula (IV) :
  • each R 1 group is independently selected from C1-4 alkyl, hydroxyalkyl or C2-4 alkenyl groups; each R 2 group is independently selected from Cs-28 alkyl or alkenyl groups, and X ⁇ is as defined above.
  • a preferred material of formula (IV) is di-hardened tallow- dimethyl ammonium chloride, sold under the Trademark ARQUAD 2HT by Akzo Nobel.
  • compositions preferably comprise a total amount of from 0.5% to 50% by weight of the cationic fabric softening compounds, preferably from 3% to 50%, more preferably from 4% to 40%, most preferably from 5% to 25%, based on the total weight of the composition, for example from 0.5 to 30 wt %, 1 to 25 wt %, 1.5 to 22 wt % and 2 to 20 wt %.
  • the iodine value of the quaternary ammonium fabric conditioning material is preferably from 0 to 80, more preferably from 0 to 60, and most preferably from 0 to 45. The iodine value may be chosen as appropriate. Essentially saturated material having an iodine value of from 0 to 5, preferably from 0 to 1 may be used in the compositions of the invention. Such materials are known as "hardened" quaternary ammonium compounds .
  • a further preferred range of iodine values is from 20 to 60, preferably 25 to 50, more preferably from 30 to 45.
  • a material of this type is a "soft" triethanolamine quaternary ammonium compound, preferably triethanolamine di-alkylester methylsulphate .
  • Typical ester quat ratios of these materials are in the range of from 25 to 45% mono ester quat, from 45 to 60 % diester quat and from 5 to 20 % triester quat, preferably from 30 to 40 % mono ester quat, from 50 to 55 % diester quat and from 10 to 15 % triester quat .
  • Iodine value refers to the measurement of the degree of unsaturation present in a material by a method of nmr spectroscopy as described in Anal. Chem., 34, 1136 (1962) Johnson and Shoolery.
  • softener materials with sufficient unsaturation can play the dual role of softener and HH material .
  • Particularly preferred materials are the ester-linked triethanolamine (TEA) quaternary ammonium compounds comprising a mixture of mono-, di- and tri-ester linked components .
  • TAA ester-linked triethanolamine
  • TEA-based fabric softening compounds comprise a mixture of mono, di- and tri-ester forms of the compound where the di-ester linked component comprises no more than 70% by weight of the fabric softening compound, preferably no more than 60%, e.g. no more than 55%, or even no more than 45% of the fabric softening compound and at least 10 % of the monoester linked component.
  • a preferred hardened type of active has a typical mono:di:tri ester distribution of 18-22 mono: 58-62 di : 18-22 tri, for example 20:60:20.
  • a soft TEA quat may have a typical mono : di : tri ester distribution of 25-45 mono: 45-60 di : 5-25 tri, for example 40: 60:10.
  • a non-ionic surfactant may be present in order to stabilise the composition, or perform other functions such as emulsifying any oil that may be present.
  • Suitable non-ionic surfactants include alkoxylated materials, particularly addition products of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids and fatty amines.
  • R is a hydrophobic moiety, typically being an alkyl or alkenyl group, said group being linear or branched, primary or secondary, and preferably having from 8 to 25, more preferably 10 to 20, and most preferably 10 to 18 carbon atoms; R may also be an aromatic group, such as a phenolic group, substituted by an alkyl or alkenyl group as described above; Y is a linking group, typically being O, CO.
  • R 1 is H or a Ci_ 4 alkyl group
  • z represents the average number of ethoxylate (EO) units present, said number being 8 or more, preferably 10 or more, more preferably 10 to 30, most preferably 12 to 25, e.g. 12 to 20.
  • non-ionic surfactants include the ethoxylates of mixed natural or synthetic alcohols in the "coco” or "tallow” chain length.
  • Preferred materials are condensation products of coconut fatty alcohol with 15-20 moles of ethylene oxide and condensation products of tallow fatty alcohol with 10-20 moles of ethylene oxide.
  • ethoxylates of secondary alcohols such as 3-hexadecanol, 2-octadecanol, 4-eicosanol, and 5-eicosanol may also be used.
  • exemplary ethoxylated secondary alcohols have formulae Ci 2 -EO(20); Ci 4 -EO(20); Ci 4 -EO(25); and Ci 6 -EOOO) .
  • Especially preferred secondary alcohols are disclosed in PCT/EP2004/003992 and include Tergitol-15-S-3.
  • Polyol-based non-ionic surfactants may also be used, examples including sucrose esters (such as sucrose monooleate) , alkyl polyglucosides (such as stearyl monoglucoside and stearyl triglucoside) , and alkyl polyglycerols .
  • sucrose esters such as sucrose monooleate
  • alkyl polyglucosides such as stearyl monoglucoside and stearyl triglucoside
  • alkyl polyglycerols alkyl polyglycerols
  • a preferred additional component in the compositions of the present invention is a fatty complexing agent.
  • Such agents typically have a Cs to C22 hydrocarbyl chain present as part of their molecular structure.
  • Suitable fatty complexing agents include Cs to C22 fatty alcohols and Cs to C22 fatty acids; of these, the Cs to C22 fatty alcohols are most preferred.
  • a fatty complexing agent is particularly valuable in compositions comprising a QAC having a single C12-28 group connected to the nitrogen head group, such as mono-ester associated with a TEA ester quat . or a softening agent of formula II, for reasons of product stability and effectiveness .
  • Preferred fatty acid complexing agents include hardened tallow fatty acid (available as Pristerene, ex Uniqema) .
  • Preferred fatty alcohol complexing agents include Ci ⁇ /Cis fatty alcohols (available as Stenol and Hydrenol, ex Cognis, and Laurex CS, ex Albright and Wilson) and behenyl alcohol, a C22 fatty alcohol, available as Lanette 22, ex Henkel.
  • the fatty complexing agent may be used at from 0.1% to 10%, particularly at from 0.2% to 5%, and especially at from 0.4 to 2% by weight, based on the total weight of the composition .
  • compositions of the invention typically comprise one or more perfumes.
  • the perfume is preferably present in an amount from 0.01 to 10% by weight, more preferably 0.05 to 5% by weight, most preferably 0.5 to 4.0% by weight, based on the total weight of the composition.
  • the Fabric softening compositions may comprise viscosity modifiers. Suitable viscosity modifiers are disclosed, for example, in WO 02/081611, US 2004/0214736, US 6827795, EP 0501714, US 2003/0104964, EP 0385749 and EP 331237.
  • compositions of the invention may contain one or more other ingredients.
  • ingredients include preservatives (e.g. bactericides), pH buffering agents, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, anti-redeposition agents, soil-release agents, electrolytes including polyelectrolytes, enzymes, optical brightening agents, anti-shrinking agents, anti-wrinkle agents, anti- spotting agents, anti-oxidants, sunscreens, anti-corrosion agents, drape imparting agents, anti-static agents, ironing aids and dyes.
  • preservatives e.g. bactericides
  • pH buffering agents perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, anti-redeposition agents, soil-release agents, electrolytes including polyelectrolytes, enzymes, optical brightening agents, anti-shrinking agents, anti-wrinkle agents, anti- spotting agents, anti-oxidants, sunscreens, anti-corrosion agents
  • compositions of the present invention are preferably rinse conditioner compositions and may be used in the rinse cycle of a domestic laundry process.
  • the composition is preferably used in the rinse cycle of a home textile laundering operation, where, it may be added directly in an undiluted state to a washing machine, e.g. through a dispenser drawer or, for a top-loading washing machine, directly into the drum. Alternatively, it can be diluted prior to use.
  • the compositions may also be used in a domestic hand-washing laundry operation.
  • compositions of the present invention are used in industrial laundry.
  • a Tergotometer (US Testing CO. Inc., Hobken, N.J.) was used to simulate the rinse stage of a washing machine.
  • ARQUAD 2HT is a di-hardened tallow-dimethyl ammonium chloride.
  • This procedure delivered 0.16 ⁇ g/g fabric of AR51 and 8 mg/g fabric of the fabric conditioner.
  • the treated fabric monitors were allowed to dry on line in a drying room over night (in dim fluorescent light during day but dark during night) .
  • the treated dried monitors were then cut in 15x7 cm x cm rectangles and placed in the Atlas Weatherometer mounting frames ready for light exposure.
  • the fabric samples were then exposed to a 2kW Xenon light source for 30 minutes with a relative humidity between 50- 60%, at the start of the test reaching 20% RH by the end of the 30 minutes period.
  • Wetting time 600+ means greater than 10 minutes. In the above cases in fact greater than 30 minutes A wetting time of > 10 minutes represents a quite hydrophobic surface.
  • Knitted cotton under similar treatment remained hydrophilic for all the treatments.
  • Fabric Softener Examples set 2
  • Stepantex UL 85 is a hard tallow TEA quat with 20% mono-, 50% di- and 30% tri-ester. It contains 85% active and 15% IPA.
  • Stepantex VT90 is a soft tallow TEA quat containing 90% active and 10% IPA.
  • Stenol 16/18 L is a fatty alcohol (complexing agent) with a mixture of C16 and C18 saturated chains.
  • Genapol C200 is a coco based ethoxylated non-ionic surfactant with 20EO.
  • Knit polyester monitors were treated with Set 2 composition in Tergotometer following the same protocol.
  • the amount of fabric conditioner added to the Tergotometer were 2g/litre which delivers same weight of treatment per weight of fabric as in Set 1.
  • the amount of photo-bleach was similar at O.Olg/1 of solution.
  • wetting time of 600+ means it has taken greater than 10 minutes.
  • Example 6 without photobleach and in Example 8 with or without photobleach the differential hydrophobicity is the reverse of the desired order. In other Examples the desired order is achieved.
  • Example 9 + AR51 the process of photo-fragmentation has gone too far resulting in hydrophilicity on both sides of the monitors. This may be because of the excess un-saturation in the composition coming both from VT90 and squalene.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
EP08865723A 2007-12-21 2008-12-12 Wirkstoff für textilbehandlung Not-in-force EP2222829B1 (de)

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GBGB0724863.6A GB0724863D0 (en) 2007-12-21 2007-12-21 Fabric treatment active
PCT/EP2008/067456 WO2009080570A1 (en) 2007-12-21 2008-12-12 Fabric treatment active

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BRPI0821304A2 (pt) 2015-06-16
WO2009080570A1 (en) 2009-07-02
AR069791A1 (es) 2010-02-17
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ZA201003054B (en) 2011-07-27
EP2222829B1 (de) 2012-02-08

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