EP1373629A1 - Fabric rinse composition containing a cationic uv absorber - Google Patents
Fabric rinse composition containing a cationic uv absorberInfo
- Publication number
- EP1373629A1 EP1373629A1 EP02706768A EP02706768A EP1373629A1 EP 1373629 A1 EP1373629 A1 EP 1373629A1 EP 02706768 A EP02706768 A EP 02706768A EP 02706768 A EP02706768 A EP 02706768A EP 1373629 A1 EP1373629 A1 EP 1373629A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- group
- composition according
- alkyl
- absorber
- 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.)
- Withdrawn
Links
Classifications
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- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2072—Aldehydes-ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34928—Salts
-
- 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
- C11D3/0015—Softening compositions liquid
-
- 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
- C11D3/26—Organic compounds containing nitrogen
- C11D3/28—Heterocyclic compounds containing nitrogen in the ring
-
- 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
- C11D3/40—Dyes ; Pigments
- C11D3/42—Brightening agents ; Blueing agents
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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
- 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
- D06M13/35—Heterocyclic compounds
- D06M13/352—Heterocyclic compounds having five-membered heterocyclic rings
-
- 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
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
-
- 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
-
- 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
- D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/06—After-treatment with organic compounds containing nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
Definitions
- the present invention relates to a fabric rinse composition containing a UV absorber and to a method of treating textiles with the composition, which method imparts to textile fiber material so treated, in addition to an excellent UV Protecting Factor(UPF) value other desirable properties.
- UPF UV Protecting Factor
- wavelengths 280-400 rim permits tanning of the epidermis. Also known is that rays of wavelengths 280-320 nm (termed UV-B radiation), cause erythemas and skin burning, which can inhibit skin tanning.
- UV-A radiation Radiation of wavelengths 320-400 nm (termed UV-A radiation) is known to induce skin tanning but can also cause skin damage, especially to sensitive skin, which is exposed to sunlight for long periods. Examples of such damage include loss of skin elasticity and the appearance of wrinkles, promotion of the onset of erythemal reaction and the inducement of phototoxic or photoallergic reactions.
- Any effective protection of the skin from the damaging effects of undue exposure to sunlight clearly needs to include means for absorbing both UV-A and UV-B components of sunlight before they reach the skin surface.
- One aspect of the desire to increase the level of skin protection against sunlight has been the consideration of additional measures, over and above the direct protection of the skin. For example, consideration has been given to the provision of protection to skin covered by clothing and thus not directly exposed to sunlight.
- Such lightweight summer clothing normally has a density of less than 200 g/m and has a sun protection factor rating between 1.5 and 20, depending on the type of fibre from which the clothing is manufactured.
- the UPF rating of a sun protectant may be defined as the multiple of the time taken for the average person wearing the sun protectant to suffer sun burning under average exposure to sun. For example, if an average person would normally suffer sun burn after 30 minutes under standard exposure conditions, a sun protectant having an UPF rating of 5 would extend the period of protection from 30 minutes to 2 hours and 30 minutes. For people living in especially sunny climates, where mean sun burn times are minimal, e.g. only 15 minutes for an average fair-skinned person at the hottest time of the day, UPF ratings of about 20 are desired for lightweight clothing.
- UVA for use in a method for effecting an increase in the UPF value of a textile fiber material (often referred to as a "UV cutting" treatment method), has to take into account the fact that the treated textile fiber material must satisfy performance criteria in a wide range of areas, such as washfastness, lightfastness and tear resistance, apart from its UPF value.
- the present invention provides a stable, concentrated fabric rinse composition
- a stable, concentrated fabric rinse composition comprising a) 0.1 to 10, preferably 0.1 to 5 % by weight of a UV absorber of formula
- U is a radical of a UV absorber selected from hydroxyphenyl-benztriazole, hydroxy- phenyltriazine and benzophenone;
- a direct bond ; C,-C 6 alkylen; C,-C 6 alkyliden; or a group of formula
- R R 2 and R 3 independently from each other are hydrogen; C ⁇ C j alkyl; or C,-C 8 alkyl which is substituted by 1 -COOR" group or by 1 to 3 OH groups, C 2 -C 8 hydroxyalkyl which is interrupted by one or more -O- groups, -(C C 8 )alkylene-COO " , -(C C 8 )alkylidene-COO " , -(C 2 -C 8 )alkylidene-S0 3 " each of which is substituted by one OH group; C 3 -C 5 alkenyl; C 5 -C 7 cycloalkyl; phenyl; tolyl; benzyl; or glycidyl; or R, toadmier with R 2 and if appropriate with R 3 and together with the N + -atom to which they are attached, form a N-heterocyclic radical which can contain 1 -3 N-atoms or one O- atom as ring members
- R' is hydrogen; C,-C 4 alkyl or C 2 -C 3 hydroxyalkyl;
- R" is hydrogen; or C C 4 alkyl
- X ' if not present in R quarantine R 2 or R 3 is a colourless organic or inorganic anion
- B° is -(CH 2 ) m -; or one of the following groups: 2 ) r ; or
- n and r are independently from each other 2 or 3; p is 1 to 6; n is 1 to 4; g is 0 or 1 ; with the proviso that
- A, Y and B are not at the same time the direct bond; b) 5 to 25% by weight, based on the total weight of the composition of a fabric softener agent; and c) water.
- the invention preferably relates to the use of a composition, wherein U in formula (1) corresponds to a UV absorber radical of formula
- UV absorber is hydrogen; C,-C 4 alkyl; C,-C 4 -Alkoxy; or halogen; and is from 0 to 3. Most preferably a UV absorber of formula
- B is C 2 -C 6 alkylene; or C 2 -C 6 alkylene which is substituted by OH and which can be inter-
- R 2 , R 3 , R', X and n are defined as in formula (1) and R 4 is as defined in formula (2).
- U corresponds to a UV absorber radical of formula
- R s , R 6 , R 7 , R 8 , R 9 and R 10 are each independently of the others hydrogen, C,-C 18 alkyl;
- R Nitrogen R 2 , R 3 , A, B, X, Y and g are defined as in formula (1).
- UV-absorber corresponds to formula
- R 2 x ' is a saturated or unsaturated mononuclear or trinuclear N-heterocyclic 3 radical containing 1 -4 N-atoms as ring members, at least one of which is quaternized; and R perpetrat R 2 , R 3 , R' and X are defined as in formula (1 ); and R 5 , R 6 , R 7 , R 8 , R 9 , R 10 are as defined in formula (3a) or (3b).
- Y is -CO-; -COO-; -OOC-; -CO-N(R')-; or -(R')N-CO-;
- B is C 2 -C 6 alkylene, which is substituted by OH;
- R 7 is hydrogen; or C,-C 6 alkyl
- R 5 R 6 R 8 , R 9 and R, 0 are independently from each other hydrogen or C,-C 6 alkyl and
- Rstrich R 2 , R 3 and R' are defined as in formula (1 ).
- UV-absorbers of formula 1 are UV-absorbers of formula 1
- Y is the group -CO-; -COO-; -OOC-; -CO-N(R')-; -(R')N-CO-; -SO.-N(R')-; -(R')N-S0 2 ;
- B is C 2 -C 6 alkylene or C 2 -C 6 alkylidene which is substituted by OH and which can be interrupted by -O- or by one or two N + X " (R') 2 -; and R réelle R 2 , R 3 , R' and X are defined as in formula (1); and
- R 5 , R 6 , R 7 , R 8 , R 9 and R, 0 are as defined as in formula (3a) or (3b). Furthermore, U preferably corresponds to a UV absorber radical of formula
- R, relief R 12 , R 13 and R, 4 independently is hydrogen, halogen, OH, C,-C 6 alkyl; or C,-C 6 alkoxy or a group of formula -0-CH 2 -CH(OH)CH 2 X, and X is -S0 3 H or an alkali metal salt thereof.
- Preferred UV absorbers according to component (a) correspond to the formula
- B is C 2 -C 6 alkylene or C 2 -C 6 alkylene which substituted by OH and which can be interrupted by -O-; and R,, R 2 and R 3 are defined as in formula (1); and R, rule R, 2 , R, 3 and R, protagonist are defined as in formula (4).
- the UV absorber should, of course, be compatible with the rinse cycle fabric softener composition.
- the UV absorber used is one which is capable of being absorbed on to the washed textile article during a rinse cycle fabric softener treatment.
- Fabric softeners (component (b)) suitable for use herein are selected from the following classes of compounds:
- Cationic quaternary ammonium salts (i) Cationic quaternary ammonium salts.
- the counter ion of such cationic quaternary ammonium salts may be a halide, such as chloride or bromide, methyl sulfate, or other ions well known in the literature.
- the counter ion is methyl sulfate or any alkyl sulfate or any halide, methyl sulfate being most preferred for the dryer-added articles of the invention.
- Examples of cationic quaternary ammonium salts include but are not limited to: 1 .
- the fabric softening compound is a water insoluble quaternary ammonium material which comprises a compound having two C 12 to C, 8 alkyl or alkenyl groups connected to the molecule via at least one ester link. It is more preferred if the quaternary ammonium material has two ester links present.
- An especially preferred ester-linked quaternary ammonium material for use in the invention can be represented by the formula:
- each R 15 group is independently selected from C,-C 4 alkyl, hydroxyalkyl or C 2 to C 4 alkenyl groups; o ft
- T is either a radical of formula (12a) — o — c — or (12b) — c — o — ; and wherein each R, 6 group is independently selected from C 8 -C 28 alkyl or C 8 -C 28 alkenyl groups; and e is an integer from 0 to 5.
- a second preferred type of quaternary ammonium material can be represented by the formula:
- R 15 , R, 6 and e are as defined in formula (12).
- Cyclic quaternary ammonium salts of the imidazolinium type such as di(hydrogenated tallow)dimethyl imidazolinium methylsulfate, 1 -ethylene-bis(2-tallow-1 -methyl) imidazolinium methylsulfate and the like; 3. Diamido quaternary ammonium salts such as: methyl-bis(hydrogenated tallow ami- doethyl)-2-hydroxethyl ammonium methyl sulfate, methyl bi(tallowamidoethyl)-2- hydroxypropyl ammonium methylsulfate and the like;
- Biodegradable quaternary ammonium salts such as N,N-di(tallowoyl-oxy-ethyl)-N,N- dimethyl ammonium methyl sulfate and N,N-di(tallowoyl-oxy-propyl)-N,N-dimethyl ammonium methyl sulfate.
- Biodegradable quaternary ammonium salts are described, for example, in U.S. Patents 4,1 37,180, 4,767,547 and 4,789,491 incorporated by reference herein.
- Preferred biodegradable quaternary ammonium salts include the biodegradable cationic diester compounds as described in U.S. Patent 4,1 37,180, herein incorporated by reference, (ii) Tertiary fatty amines having at least one and preferably two C 8 -C 30 , preferably C, 2 -C 22 alkyl chains. Examples include hardened tallow-di-methylamine and cyclic amines such as 1 - (hydrogenated tallow)amidoethyl-2-(hydrogenated tallow) imidazoline. Cyclic amines which may be employed for the compositions herein are described in U.S. Patent 4,806,255 incorporated by reference herein.
- Carboxylic acids having 8 to 30 carbons atoms and one carboxylic group per molecule.
- the alkyl portion has 8 to 30, preferably 12 to 22 carbon atoms.
- the alkyl portion may be linear or branched, saturated or unsaturated, with linear saturated alkyl preferred.
- Stearic acid is a preferred fatty acid for use in the composition herein. Examples of these carboxylic acids are commercial grades of stearic acid and palmitic acid, and mixtures thereof which may contain small amounts of other acids.
- esters of polyhydric alcohols such as sorbitan esters or glycerol stearate.
- Sorbitan esters are the condensation products of sorbitol or iso-sorbitol with fatty acids such as stearic acid.
- Preferred sorbitan esters are monoalkyl.
- SPAN 60 SPAN 60 (ICI) which is a mixture of sorbitan and isosorbide stearates.
- Preferred fabric softeners for use herein are acyclic quaternary ammonium salts. Di(hydrogenated)tallowdimethyl ammonium methylsulfate is most widely used for dryer articles of this invention. Mixtures of the above mentioned fabric softeners may also be used.
- composition according to the present invention may also contain a minor proportion of one or more adjuvants.
- adjuvants include emulsifiers, perfumes, colouring dyes, opacifiers, fluorescent whitening agents, bactericides, nonionic surfactants, anti-gelling agents such as nitrites or nitrates of alkali metals, especially sodium nitrate, and corrosion inhibitors such as sodium silicate.
- the amount of each of these optional adjuvants preferably ranges from 0.05 to 5% by weight of the composition.
- a particularly preferred optional adjuvant is a cationic, amphoteric or anionic fluorescent whitening agent as disclosed in EP-A-0,659,877, from page 9 to page 15, line 56.
- the present invention also provides a method for the improvement of UPF of a textile article, comprising applying, to a previously washed article, a fabric rinse composition comprising: a) 0.1 to 10, preferably 0.1 to 5 % by weight of a UV absorber of formula (1), based on the total weight of the composition; b) 5 to 25%, especially from 10 to 20% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) water.
- the method and composition of the present invention in addition to providing protection to the skin, also increase the useful life of a textile article treated according to the present invention, for example by preserving its tear strength and/or its lightfastness or reducing the fading from sunlight.
- the present invention also provides a method for the reducing of the fading of fabrics from sunlight, comprising applying, to a previously washed article, a fabric rinse composition comprising: a) 0.1 to 10, preferably 0.1 to 5 % by weight of a UV absorber of formula (1 ), based on the total weight of the composition; b) 5 to 25%, especially from 10 to 20% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) water.
- a fabric rinse composition comprising: a) 0.1 to 10, preferably 0.1 to 5 % by weight of a UV absorber of formula (1 ), based on the total weight of the composition; b) 5 to 25%, especially from 10 to 20% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) water.
- composition deposit from about 0.5 mg/g fabric to about 5 mg/g fabric of the UV absorber of formula (1) onto the fabric to reduce the sun fading of fabric.
- the textile article treated according to the method of the present invention may be composed of any of a wide range of types of fibers such as wool, polyamide, cotton, polyester, polyacrylic, silk or any mixture thereof.
- reaction mass 100 g of the compound of formula (5a) are suspended in 650 ml t-amyl alcohol. Then 17.3 g of pulverized potassium hydroxide are added and the reaction mass is warmed up indirectly to 80°C and then stirred for one hour at 80°C. Then within 5 min 77 g of an aqueous solution of 3-chloro-2-hydroxypropyl)trimethyl ammonium chloride are added dropwise and stirred at 80°C. After 30 minutes spontaneous crystallization occurs forming a yellow suspension. Then the reaction mass is cooled indirectly to 60°C and then filtered over a prewarmed pressure filter funnel.
- Detergent dosage 4 g/l EE 77 (phosphate containing standard detergent which is free of fluorescent whitening and bleaching agents )
- Liquor ratio 1 :20
- Rinsing is carried out with tap water for 30 seconds and the spin dried.
- the fabric is spin dried at 60°C; 1 and 3 wash cycles.
- the UPF of the dried softener treated goods are determined by measurement of the UV light transmitted through the textile, using a double grating spectrophotometer fitted with an Ulbricht bowl. Calculation of UPF is conducted as described by B.L.Diffey and J.Robson in j. Soc. Cosm. Chem. 40 (1989), pp. 130-131 .
- the fabrics are rinsed with tap water for 30 seconds and spin dried.
- the fabric is spin dried at 60°C and irradiated in an ATLAS Weather-O-Meter G65A under the following conditions:
- the CIE color system evaluates the color of a fabric sampel in terms of the L*, a*, b* coordinates which are determinded from spectrophotometer readings.
- L*, a*, b* are as described in Colorimetry, 2 nd Edition, CIE Publication no. 15.2, published by Bureau, Central de la CIE, Paris 1982).
- the ⁇ E value is defined by the following equation:
- ⁇ E ⁇ (L f * - L*) 2 + (a * - a *) 2 + (b f * - b *) 2 ⁇ ' /2
- subscripts i and f refer to the values as measured with or without irradiation of the sample, respectively.
Abstract
Disclosed is a fabric rise composition comprising a) 0.1 to 10 % by weight of a UV absorber of formula (1), wherein U is a radical of a UV absorber selected from hydroxyphenyl-benztriazole, hydroxyphenyl-triazine and benzophenone; A direct bond; C1-C6alkylen; C1-C6alkyliden; or a group of formula (1a); Y direct bond; or the group -CO-; -COO-; -OOC-; -CO-N(R')-; -(R')N-CO-; -SO2-N(R')-; -R(R')N-SO2; a group of formula (1b); (1c); (1d); or (1e); B direct bond; C2-C6alkylene or C2-C6alkylidene which is substituted by OH and which can be interrupted by -O- or by one or two N+X-(R')2-; or is a group of formula (1g), or (h); or the group (2) is a saturated or unsaturated mononuclear or trinuclear N-heterocyclic radical containing 1-4 N-atoms as ring members, at least one of which is quaternized; R1, R2 and R3 independently from each other are hydrogen; C1-C8alkyl; or C1-C8alkyl which is substituted by 1 -COOR'' group or by 1 to 3 OH groups, C2-C8hydroxyalkyl which is interrupted by one or more -O- groups, -(C1-C8)alkylene-COO-, -(C1-C8)alkylidene-COO?-, -(C2-C8)alkylidene-SO3-¿ each of which is substituted by one OH group; C¿3?-C5alkenyl; C5-C7cycloalkyl; phenyl; tolyl; benzyl; or glycidyl; or R1 together with R2 and if appropriate with R3 and together with the N?+¿-atom to which they are attached, form a N-heterocyclic radical which can contain 1-3 N-atoms or one O-atom as ring members; R' is hydrogen; C¿1?-C4alkyl or C2-C3 hydroxyalkyl; R'' is hydrogen; or C1-C4alkyl and X?-¿ if not present in R¿1?, R2 or R3 is a colourless organic or inorganic anion. B° is -(CH2)m-; or one of the following groups: (3); (4); or (5); m and r are independently from each other 2 or 3; p is 1 to 6; n is 1 to 4; g is 0 or 1; with the proviso that A, Y and B are not the same time the direct bond; b) 5 to 25 % by weight, based on the total weight of the composition of a fabric softener agent; and c) water.
Description
Fabric Rinse Composition containing a cationic UV absorber
The present invention relates to a fabric rinse composition containing a UV absorber and to a method of treating textiles with the composition, which method imparts to textile fiber material so treated, in addition to an excellent UV Protecting Factor(UPF) value other desirable properties.
It is known that light radiation of wavelengths 280-400 rim permits tanning of the epidermis. Also known is that rays of wavelengths 280-320 nm (termed UV-B radiation), cause erythemas and skin burning, which can inhibit skin tanning.
Radiation of wavelengths 320-400 nm (termed UV-A radiation) is known to induce skin tanning but can also cause skin damage, especially to sensitive skin, which is exposed to sunlight for long periods. Examples of such damage include loss of skin elasticity and the appearance of wrinkles, promotion of the onset of erythemal reaction and the inducement of phototoxic or photoallergic reactions.
Any effective protection of the skin from the damaging effects of undue exposure to sunlight clearly needs to include means for absorbing both UV-A and UV-B components of sunlight before they reach the skin surface.
Traditionally, protection of exposed human skin against potential damage by the UV components in sunlight has been effected by directly applying to the skin a preparation containing a UV absorber.
One aspect of the desire to increase the level of skin protection against sunlight has been the consideration of additional measures, over and above the direct protection of the skin. For example, consideration has been given to the provision of protection to skin covered by clothing and thus not directly exposed to sunlight.
Most natural and synthetic textile materials are at least partially permeable to UV components of sunlight. Accordingly, the mere wearing of clothing does not necessarily provide
skin beneath the clothing with adequate protection against damage by UV radiation. Although clothing containing a deeply colored dye and/or having a tight weave texture may provide a reasonable level of protection to skin beneath it, such clothing is not practical in hot sunny climates, from the standpoint of the personal comfort of the wearer.
There is a need, therefore, to provide protection against UV radiation for skin which lies underneath clothing, including lightweight summer clothing, which is undyed or dyed only in pale shades. Depending on the nature of the dyestuff, even skin beneath clothing dyed in some dark shades may also require protection from UV radiation.
Such lightweight summer clothing normally has a density of less than 200 g/m and has a sun protection factor rating between 1.5 and 20, depending on the type of fibre from which the clothing is manufactured.
The UPF rating of a sun protectant (sun cream or clothing) may be defined as the multiple of the time taken for the average person wearing the sun protectant to suffer sun burning under average exposure to sun. For example, if an average person would normally suffer sun burn after 30 minutes under standard exposure conditions, a sun protectant having an UPF rating of 5 would extend the period of protection from 30 minutes to 2 hours and 30 minutes. For people living in especially sunny climates, where mean sun burn times are minimal, e.g. only 15 minutes for an average fair-skinned person at the hottest time of the day, UPF ratings of about 20 are desired for lightweight clothing.
The selection of a suitable UVA, for use in a method for effecting an increase in the UPF value of a textile fiber material (often referred to as a "UV cutting" treatment method), has to take into account the fact that the treated textile fiber material must satisfy performance criteria in a wide range of areas, such as washfastness, lightfastness and tear resistance, apart from its UPF value.
Another major problem for consumers in many parts of the world is the fading of colored fabrics by sunlight (so-called "photo-fading") during wear and during drying. Thus suscep-
tible fabrics in temperature and high latitude regions in addition to those in the tropics can be severely faded. Photo- fading of fabrics is of specific concern to consumers because the contrast between exposed and unexposed areas makes it particularly noticeable.
Surprisingly it was found that the use of specific UV absorbers in a fabric rinse composition imparts enhanced UPF, and simultaneously effectively prevents the photo-fading of said fabric.
Therefore the present invention provides a stable, concentrated fabric rinse composition comprising a) 0.1 to 10, preferably 0.1 to 5 % by weight of a UV absorber of formula
(1 ) U-(0)-A-Y-B— N+— R2 x" , wherein
R3
U is a radical of a UV absorber selected from hydroxyphenyl-benztriazole, hydroxy- phenyltriazine and benzophenone;
A direct bond; C,-C6alkylen; C,-C6alkyliden; or a group of formula
Y direct bond; or the group -CO-; -COO-; -OOC-; -CO-N(R')-; -(R')N-CO-; -SO.-N(R')-; -(R')N-SO-; a group of formula
(1 b)
(1 d) -co — — cnH— co-N(R')- ; or (1 e) -co — N — cnH— co-o-
/Rι | ^
CnH2n-CO-N(R')-B°-N+— R2 χ- CnH2n-COO-B°-N+— R2 X"
B direct bond; C2-C6alkylene or C2-C6alkylidene which is substituted by OH and which can be interrupted by -O- or by one or two N+X'(R')2-;
or is a group of formula (1 g)
or the group — B — x" is a saturated or unsaturated mononuclear or trinu-
clear N-heterocyclic radical containing 1 -4 N-atoms as ring members, at least one of which is quaternized;
R R2 and R3 independently from each other are hydrogen; C^Cjalkyl; or C,-C8alkyl which is substituted by 1 -COOR" group or by 1 to 3 OH groups, C2-C8hydroxyalkyl which is interrupted by one or more -O- groups, -(C C8)alkylene-COO", -(C C8)alkylidene-COO", -(C2-C8)alkylidene-S03 " each of which is substituted by one OH group; C3-C5alkenyl; C5-C7cycloalkyl; phenyl; tolyl; benzyl; or glycidyl; or R, togehter with R2 and if appropriate with R3 and together with the N+-atom to which they are attached, form a N-heterocyclic radical which can contain 1 -3 N-atoms or one O- atom as ring members
R' is hydrogen; C,-C4alkyl or C2-C3hydroxyalkyl;
R" is hydrogen; or C C4alkyl;
X' if not present in R„ R2 or R3 is a colourless organic or inorganic anion;
B° is -(CH2)m-; or one of the following groups: 2)r ; or
(CH2)- i1+— (CH2)-N ?:+-(CH2)-
R. R2
2X-
m and r are independently from each other 2 or 3; p is 1 to 6; n is 1 to 4; g is 0 or 1 ; with the proviso that
A, Y and B are not at the same time the direct bond; b) 5 to 25% by weight, based on the total weight of the composition of a fabric softener agent; and c) water.
The invention preferably relates to the use of a composition, wherein U in formula (1) corresponds to a UV absorber radical of formula
(2) wherein
is hydrogen; C,-C4alkyl; C,-C4-Alkoxy; or halogen; and is from 0 to 3.
Most preferably a UV absorber of formula
(2a) , is used as component (a), wherein
B is C2-C6alkylene; or C2-C6alkylene which is substituted by OH and which can be inter-
OH
I rupted by -O- or by one of -N+X"(R')2- ; most preferably -CH2-CH— CH2- ; and R„ R2, R3, R', X and n are defined as in formula (1) and R4 is as defined in formula (2).
Preferably U corresponds to a UV absorber radical of formula
wherein
Rs, R6, R7, R8, R9 and R10 are each independently of the others hydrogen, C,-C18alkyl;
I 1
C5-C7cycloalkyI; halogen; or a radical of formula (3a,) _(O)-A-Y-B-N+-R2 X" wherein
R„ R2, R3, A, B, X, Y and g are defined as in formula (1).
Most preferably the UV-absorber corresponds to formula
C3a,)
-wherein
Y is the group -CO-; -COO-; -OOC-; -CO-N(R')-; -(R')N-CO-; -S02-N(R')-; -(R')N-S02;
B is C2-C6alkylene or C2-C6alkylidene which is substituted by OH and which can be interrupted by -O- or by one or two N+X'(R')2-;or
/R1
— B — N^— R2 x' is a saturated or unsaturated mononuclear or trinuclear N-heterocyclic 3 radical containing 1 -4 N-atoms as ring members, at least one of which is quaternized; and R„ R2, R3, R' and X are defined as in formula (1 ); and R5, R6, R7, R8, R9, R10 are as defined in formula (3a) or (3b).
Most preferred are UV absorbers of formula (3a,) wherein
Y is -CO-; -COO-; -OOC-; -CO-N(R')-; or -(R')N-CO-; B is C2-C6alkylene, which is substituted by OH;
R7 is hydrogen; or C,-C6alkyl;
R5 R6 R8, R9 and R,0 are independently from each other hydrogen or C,-C6alkyl and
R„ R2, R3 and R' are defined as in formula (1 ).
Further preferred are UV-absorbers of formula
Y is the group -CO-; -COO-; -OOC-; -CO-N(R')-; -(R')N-CO-; -SO.-N(R')-; -(R')N-S02;
B is C2-C6alkylene or C2-C6alkylidene which is substituted by OH and which can be interrupted by -O- or by one or two N+X"(R')2-; and R„ R2, R3, R' and X are defined as in formula (1); and
R5, R6, R7, R8, R9 and R,0 are as defined as in formula (3a) or (3b).
Furthermore, U preferably corresponds to a UV absorber radical of formula
, wherein
R,„ R12, R13 and R,4 independently is hydrogen, halogen, OH, C,-C6alkyl; or C,-C6alkoxy or a group of formula -0-CH2-CH(OH)CH2X, and X is -S03H or an alkali metal salt thereof.
Preferred UV absorbers according to component (a) correspond to the formula
wherein
B is C2-C6alkylene or C2-C6alkylene which substituted by OH and which can be interrupted by -O-; and R,, R2 and R3 are defined as in formula (1); and R,„ R,2, R,3 and R,„ are defined as in formula (4).
The following cationic UV absorbers used according to the invention may be mentioned by way of example:
The UV absorber used in the present composition readily absorbs UV light, especially in the range I = 300 to 400 nm, and converts the absorbed energy, by a chemical intermediate reaction, into non-interfering, stable compounds or into non-interfering forms of energy. The UV absorber should, of course, be compatible with the rinse cycle fabric softener composition.
Preferably, the UV absorber used is one which is capable of being absorbed on to the washed textile article during a rinse cycle fabric softener treatment. Fabric softeners (component (b)) suitable for use herein are selected from the following classes of compounds:
(i) Cationic quaternary ammonium salts. The counter ion of such cationic quaternary ammonium salts may be a halide, such as chloride or bromide, methyl sulfate, or other ions well known in the literature. Preferably the counter ion is methyl sulfate or any alkyl sulfate or any halide, methyl sulfate being most preferred for the dryer-added articles of the invention.
Examples of cationic quaternary ammonium salts include but are not limited to: 1 . Acyclic quaternary ammonium salts having at least two C8 to C30, preferably C,2 to C22 alkyl or alkenyl chains, such as: ditallowdimethyl ammonium methylsulfate, di(hydrogenated
tallow)dimethyl ammonium methylsulfate, distearyldimethyl ammonium methylsulfate or chloride, dicocodimethyl ammonium methylsulfate and the like. It is especially preferred if the fabric softening compound is a water insoluble quaternary ammonium material which comprises a compound having two C12 to C,8 alkyl or alkenyl groups connected to the molecule via at least one ester link. It is more preferred if the quaternary ammonium material has two ester links present. An especially preferred ester-linked quaternary ammonium material for use in the invention can be represented by the formula:
wherein each R15 group is independently selected from C,-C4alkyl, hydroxyalkyl or C2 to C4 alkenyl groups; o ft
T is either a radical of formula (12a) — o — c — or (12b) — c — o — ; and wherein each R,6 group is independently selected from C8-C28 alkyl or C8-C28alkenyl groups; and e is an integer from 0 to 5.
A second preferred type of quaternary ammonium material can be represented by the formula:
wherein R15, R,6 and e are as defined in formula (12).
2. Cyclic quaternary ammonium salts of the imidazolinium type such as di(hydrogenated tallow)dimethyl imidazolinium methylsulfate, 1 -ethylene-bis(2-tallow-1 -methyl) imidazolinium methylsulfate and the like;
3. Diamido quaternary ammonium salts such as: methyl-bis(hydrogenated tallow ami- doethyl)-2-hydroxethyl ammonium methyl sulfate, methyl bi(tallowamidoethyl)-2- hydroxypropyl ammonium methylsulfate and the like;
4. Biodegradable quaternary ammonium salts such as N,N-di(tallowoyl-oxy-ethyl)-N,N- dimethyl ammonium methyl sulfate and N,N-di(tallowoyl-oxy-propyl)-N,N-dimethyl ammonium methyl sulfate. Biodegradable quaternary ammonium salts are described, for example, in U.S. Patents 4,1 37,180, 4,767,547 and 4,789,491 incorporated by reference herein.
Preferred biodegradable quaternary ammonium salts include the biodegradable cationic diester compounds as described in U.S. Patent 4,1 37,180, herein incorporated by reference, (ii) Tertiary fatty amines having at least one and preferably two C8-C30, preferably C,2-C22 alkyl chains. Examples include hardened tallow-di-methylamine and cyclic amines such as 1 - (hydrogenated tallow)amidoethyl-2-(hydrogenated tallow) imidazoline. Cyclic amines which may be employed for the compositions herein are described in U.S. Patent 4,806,255 incorporated by reference herein.
(iii) Carboxylic acids having 8 to 30 carbons atoms and one carboxylic group per molecule. The alkyl portion has 8 to 30, preferably 12 to 22 carbon atoms. The alkyl portion may be linear or branched, saturated or unsaturated, with linear saturated alkyl preferred. Stearic acid is a preferred fatty acid for use in the composition herein. Examples of these carboxylic acids are commercial grades of stearic acid and palmitic acid, and mixtures thereof which may contain small amounts of other acids.
iv) Esters of polyhydric alcohols such as sorbitan esters or glycerol stearate. Sorbitan esters are the condensation products of sorbitol or iso-sorbitol with fatty acids such as stearic acid. Preferred sorbitan esters are monoalkyl. A common example of sorbitan ester is SPAN 60 (ICI) which is a mixture of sorbitan and isosorbide stearates.
(v) Fatty alcohols, ethoxylated fatty alcohols, alkyphenols, ethoxylated alkyphenols, ethoxylated fatty amines, ethoxylated monoglycerides and ethoxylated diglycerides.
(vi) Mineral oils, and polyols such as polyethylene glycol.
These softeners are more definitively described in U.S. Patent 4,1 34,838 the disclosure of which is incorporated by reference herein. Preferred fabric softeners for use herein are acyclic quaternary ammonium salts. Di(hydrogenated)tallowdimethyl ammonium methylsulfate is most widely used for dryer articles of this invention. Mixtures of the above mentioned fabric softeners may also be used.
In addition, the composition according to the present invention may also contain a minor proportion of one or more adjuvants. Examples of adjuvants include emulsifiers, perfumes, colouring dyes, opacifiers, fluorescent whitening agents, bactericides, nonionic surfactants, anti-gelling agents such as nitrites or nitrates of alkali metals, especially sodium nitrate, and corrosion inhibitors such as sodium silicate.
The amount of each of these optional adjuvants preferably ranges from 0.05 to 5% by weight of the composition.
A particularly preferred optional adjuvant is a cationic, amphoteric or anionic fluorescent whitening agent as disclosed in EP-A-0,659,877, from page 9 to page 15, line 56. The present invention also provides a method for the improvement of UPF of a textile article, comprising applying, to a previously washed article, a fabric rinse composition comprising: a) 0.1 to 10, preferably 0.1 to 5 % by weight of a UV absorber of formula (1), based on the total weight of the composition; b) 5 to 25%, especially from 10 to 20% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) water.
The method and composition of the present invention, in addition to providing protection
to the skin, also increase the useful life of a textile article treated according to the present invention, for example by preserving its tear strength and/or its lightfastness or reducing the fading from sunlight.
Therefore the present invention also provides a method for the reducing of the fading of fabrics from sunlight, comprising applying, to a previously washed article, a fabric rinse composition comprising: a) 0.1 to 10, preferably 0.1 to 5 % by weight of a UV absorber of formula (1 ), based on the total weight of the composition; b) 5 to 25%, especially from 10 to 20% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) water.
The composition deposit from about 0.5 mg/g fabric to about 5 mg/g fabric of the UV absorber of formula (1) onto the fabric to reduce the sun fading of fabric.
The textile article treated according to the method of the present invention may be composed of any of a wide range of types of fibers such as wool, polyamide, cotton, polyester, polyacrylic, silk or any mixture thereof.
Treatment of fabric with compositions of the present invention repeatedly during the rinse cycle of a typical laundering process may result in higher deposition levels, which contributes even further to the sun-fading benefit. The following Examples further illustrate the present invention.
Example 1 : Preparation of compound of formula (5): Reaction scheme:
(5a)
(5)
100 g of the compound of formula (5a) are suspended in 650 ml t-amyl alcohol. Then 17.3 g of pulverized potassium hydroxide are added and the reaction mass is warmed up indirectly to 80°C and then stirred for one hour at 80°C. Then within 5 min 77 g of an aqueous solution of 3-chloro-2-hydroxypropyl)trimethyl ammonium chloride are added dropwise and stirred at 80°C. After 30 minutes spontaneous crystallization occurs forming a yellow suspension. Then the reaction mass is cooled indirectly to 60°C and then filtered over a prewarmed pressure filter funnel.
620 ml of a yellowish clear filtrate is obtained. The suction cake is washed 4 times with 50 ml of acetone, first air-dried and then at 70°C in vacuum.
148 g of a beige powder is obtained.
'H-NMR d6-DMSO, values in ppm:
Example 2: Preparation of compound of formula (6): Reaction Scheme:
(6a)
(6)
The process is carried out according to the proceeding of Example 1 with the difference that compound (6a) is the starting compound and cyclohexanol is used as solvent.
^- MR in d6-DMSO, values in ppm:
Example 3: Preparation of compound of formula (14): Reaction Scheme:
(14)
The process is carried out according to the proceeding of Example 1 with the difference that (3-chloro-2-hydroxypropyl)-dodecyl-dimethyl-ammoniumchloride as reactant and 2-methyl- 2-butanol as solvent are used.
1 H-NMR in d6-DMSO, values in ppm
Example 4: Improvement of UPF
5 g of bleached cotton fabric (weave) are washed/rinsed in a linitest applying the following conditions:
Main wash:
Detergent dosage: 4 g/l EE 77 (phosphate containing standard detergent which is free of fluorescent whitening and bleaching agents ) Liquor ratio: 1 :20
Duration: 15 minutes
Temperature: 25°C
Rinsing is carried out with tap water for 30 seconds and the spin dried.
Rinse bath: Softener dosage: 1 ,66 g/l concentrated Esterquat or 5 g/l diluted DSDMAC Liquor ration: 1 :40 Duration: 15 minutes Temperature: 25°C
The fabric is spin dried at 60°C; 1 and 3 wash cycles.
The UPF of the dried softener treated goods are determined by measurement of the UV light transmitted through the textile, using a double grating spectrophotometer fitted with an Ulbricht bowl. Calculation of UPF is conducted as described by B.L.Diffey and J.Robson in j. Soc. Cosm. Chem. 40 (1989), pp. 130-131 .
The results are shown in Table 1 :
The results in Table 2 clearly demonstrate the improvement of the UPF values of the cotton substrates treated with rinse compositions according to the present invention. Example 2: Photo Fading Inhibition Six differently colored cotton fabrics
A: Reactive Black 005 B: Reactive Red 226 C: Reactive Blue 013 D: Reactive Red 264 E: Reactive Red 228 F: Reactive Red 002 are separately washed and rinsed in a Linitest applying the following conditions:
Main wash:
Detergent dosage: 4 g/l ECE77
Liquor Ration: 1 :20
Duration: 15 minutes
Temperature: 25°C
The fabrics are rinsed with tap water for 30 seconds and spin dried.
Rinse bath: Softener dosage: 4 g/l DSDMAC formulation Liquor ration: 1 :20 Duration: 15 minutes Temperature: 25°C
The fabric is spin dried at 60°C and irradiated in an ATLAS Weather-O-Meter G65A under the following conditions:
Filter: Boro/Boro
Irradiation lamp: 3.5 kw
Irradiation onto the fabric: 0.22 W/m2
Dry bulb: 29.3°C
Wet bulb: 21 .9°C
Wet bulb depression: 7.3°C
Rel. humidity 43%
Duration: 7 h
10 wash/rinse/irradiation cycles
Effect Evaluation CIE Color Measurement
The CIE color system evaluates the color of a fabric sampel in terms of the L*, a*, b* coordinates which are determinded from spectrophotometer readings. (L*, a*, b* are as described in Colorimetry, 2nd Edition, CIE Publication no. 15.2, published by Bureau, Central de la CIE, Paris 1982). The ΔE value is defined by the following equation:
ΔE = {(Lf* - L*)2 + (a * - a *)2 + (bf* - b *)2}'/2 where the subscripts i and f refer to the values as measured with or without irradiation of the sample, respectively.
The CIE color measurements of the colored fabric washed/rinsed without UV- aborber/irradiated (reference = not irradiated) and the colored fabric washed/rinsed with UV-absorber/irradiated (reference = not irradiated) obtained the following results:
The results in the table show that the colored cotton fabrics treated according to the process of the present invention show a remarkable photo-fading inhibition.
Claims
1. fabric rinse composition comprising a) 0.1 to 10 % by weight of a UV absorber of formula
(1) U-(0)-A-Y-B— N+— R2 x" , wherein R3
U is a radical of a UV absorber selected from hydroxyphenyl-benztriazole, hydroxyphenyl- triazine and benzophenone; A direct bond; C,-C6alkylen; C,-C6alkyliden; or a group of formula (1 a)
Y direct bond; or the group -CO-; -COO-; -OOC-; -CO-N(R')-; -(R')N-CO-; -S02-N(R')-; -(R')N-S02; a group of formula (1 b) ;
or χ-
B direct bond; C2-C6alkylene or C2-C6alkylidene which is substituted by OH and which can be interrupted by -O- or by one or two N+X'(R')2-;
or is a group of formula (1 g)
/R1 or the group — B — N^—R2 X" is a saturated or unsaturated mononuclear or trinuciear
R
3
N-heterocyclic radical containing 1 -4 N-atoms as ring members, at least one of which is quaternized;
R„ R2 and R3 independently from each other are hydrogen; C,-Cβalkyl; or C,-C8alkyl which is substituted by 1 -COOR" group or by 1 to 3 OH groups, C2-C8hydroxyalkyl which is interrupted by one or more -O- groups, -(C,-C8)alkylene-COO", -(C,-C8)alkyli- dene-COO", -(C2-C8)alkylidene-S03 " each of which is substituted by one OH group; C3-
C5alkenyl; C5-C7cydoalkyl; phenyl; tolyl; benzyl; or glycidyl; or R, togehter with R2 and if appropriate with R3 and together with the N+-atom to which they are attached, form a
N-heterocyclic radical which can contain 1 -3 N-atoms or one O-atom as ring members
R' is hydrogen; C,-C4alkyl or C2-C3hydroxyalkyl;
R" is hydrogen; or C,-C4alkyl and
X' if not present in R„ R2 or R3 is a colourless organic or inorganic anion;
B° is -(CH2)m-; or one of the following groups: 2)~ ;
2X-
m and r are independently from each other 2 or 3; p is 1 to 6; n is 1 to 4; g is 0 or 1 ; with the proviso that
A, Y and B are not at the same time the direct bond; b) 5 to 25% by weight, based on the total weight of the composition of a fabric softener agent; and c) water.
2. A composition according to claim 1 wherein U corresponds to a UV absorber radical of formula
wherein
R4 is hydrogen; C,-C4alkyl; C,-C4-Alkoxy; or halogen; and n is from 0 to 3.
3. A composition according to claim 1 or 2 wherein the UV-absorber corresponds to formula
(2a) , wherein
B is C2-C6alkylene; or C2-C6alkylene which is substituted by OH and which can be interrupted by -O- or by one of -N+X'(R')2- ; and R„ R2, R3, R', X and n are defined as in claim 1; and
R4, is defined as in claim 2.
4. A composition according to claim 3, wherein
OH B is -CH2-CH-CH2-
5. A composition according to claim 1, wherein U corresponds to a UV absorber radical of formula
(3a) or (3b) , wherein
R5, R6, R7, R8, R9 and R10 are each independently of the others hydrogen, C,-C,8alkyl;
C5-C7cycloalkyl; halogen; or a radical of formula (3a,) _ro _A.Y.B. ,+_R x- ;
R3 and wherein R„ R2, R3, A, B, X, Y and g are defined as in formula (1).
6. A composition according to claim 5, wherein the UV-absorber corresponds to formula
(3a,) , wherein
Y is the group -CO-; -COO-; -OOC-; -CO-N(R')-; -(R')N-CO-; -S02-N(R')-; -(R')N-S02; B is C2-C6alkylene or C2-C6alkylidene which is substituted by OH and which can be interrupted by -O- or by one or two N+X"(R')2-;
/R1 or the group — B — N^— R2 x' is a saturated or unsaturated mononuclear or trinuclear
R
3
N-heterocyclic radical containing 1 -4 N-atoms as ring members, at least one of which is quaternized; R,, R2, R3, R' and X are as defined as in claim 1 ; and R5, R6, R7, R8, R9 and R,0 are defined as in claim 5.
7. A composition according to claim 6, wherein
Y is -CO-; -COO-; -OOC-; -CO-N(R')-; or -(R')N-CO-;
B is C2-C6alkylene, which is substituted by OH; R7 is hydrogen; or C,-C6alkyl;
R5 R6 R8, R9 and R,0 are independently from each other hydrogen or C,-C6alkyl; and
R„ R2, R3 and R' are as defined in claim 1.
8. A composition according to claim 5, wherein the UV-absorber of component (a) corresponds to formula
W , wherein
Y is the group -CO-; -COO-; -OOC-; -CO-N(R')-; -(R')N-CO-; -S02-N(R')-; -(R')N-S02; B is C2-C6alkylene or C2-C6alkylidene which is substituted by OH and which can be interrupted by -O- or by one or two N+X'(R')2-; and R„ R2, R3/ R' and X are as defined as in claim 1; and R5, R6, R7, R8, R9 and R,0 are defined as in claim 5.
9. A composition according to claim 1 , wherein U corresponds to a UV absorber radical of formula
R,„ R,2, R,3 and R,4 independently from each other are hydrogen, halogen, OH, C,-C6alkyl; C,-C6alkoxy; or a group of formula -0-CH2-CH(OH)CH2X; and
X is -S03H or an alkali metal salt thereof.
10. A composition according to claim 9, wherein the UV absorber of component (a) corresponds to the formula
B is C2-C6alkylene or C2-C6alkylene which is substituted by OH and which can be interrupted by -0-; R„ R2, R3, are defined as in claim 1; and R„, R,2, R,3 and R,4are defined as in claim 9.
11 . A composition according to any of the preceding claims in which the fabric care ingredient is selected from cationic quaternary ammonium salts, tertiary fatty amines having at least one C8-C30 alkyl chain, carboxylic acids having 8 to 30 carbons atoms and one carboxylic group per molecule, esters of polyhydric alcohols, fatty alcohols, ethoxylated fatty alcohols, alkyphenols, ethoxylated alkyphenols, ethoxylated fatty amines, ethoxylated mono- glycerides and ethoxylated diglycerides, mineral oils and polyols.
12. A composition according to claim 11 , wherein the cationic quaternary ammonium salt fabric softener is selected from acyclic quaternary ammonium salts having at least two C8 to C30 alkyl or alkenyl chains, cyclic quaternary ammonium salts, diamido quaternary ammonium salts and biodegradable quaternary ammonium salts.
13. A composition according to claim 12, wherein acyclic quaternary ammonium salts correspond to formula
wherein each R,s group is independently selected from C,-C4alkyl, hydroxyalkyl or C2-C4al- kenyl ; o o
T is either a radical of formula (12a) — o — c — or (12b) — c — o — ;
and wherein each R,6 group is independently selected from C8-C28alkyl or C8-C28alkenyl groups; and e is an integer from 0 to 5.
14. A composition according to claim 13, wherein acyclic quaternary ammonium salts correspond to formula
wherein
R15 and R,6, independently from each other is C,-C4alkyl, hydroxyalkyl; or C2-C4alkenyl; and e is an integer from 0 to 3.
15. A composition according to claim 13, wherein the acyclic quaternary ammonium salt is di-(palmcarboxyethyl)-hydroxyethyl-methylammonium-methosulfate.
16. A composition according to claim 12, wherein the acyclic quaternary ammonium salt is selected from ditallowdimethyl ammonium methylsulfate, di(hydrogenated tallow)dimethyl ammonium methylsulfate, distearyldimethyl ammonium methylsulfate or chloride and dico- codimethyl ammonium methylsulfate.
17. A composition according to claim 11 or 12, in which the cyclic quaternary ammonium salts are selected from di(hydrogenated tallow)dimethyl imidazolinium methylsulfate, 1 - ethylene-bis(2-tallow-1 -methyl) imidazolinium methylsulfate.
18. A composition according to claim 11 or 12, in which the diamido quaternary ammonium salts are selected from methyl-bis(hydrogenated tallow amidoethyl)-2-hydroxethyl ammonium methyl sulfate and methyl bi(tallowamidoethyl)-2-hydroxypropyl ammonium methylsulfate.
19. A composition according to claim 1 1 or 12, in which the biodegradable quaternary ammonium salts are selected from N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethyl ammonium methyl sulfate and N,N-di(tallowoyl-oxy-propyl)-N,N-dimethyl ammonium methyl sulfate
20. A composition according to any of the preceding claims which also contains an adjuvant selected from an emulsifier, perfume, colouring dye, opacifier, fluorescent whitening agent, bactericide, nonionic surfactant, anti-gelling agent and corrosion inhibitor.
21 . A method for the improvement of UPF of a textile article, comprising applying, to a previously washed article, a fabric rinse composition comprising a) 0.1 to 10% by weight of a UV absorber of formula (1 ), based on the total weight of the composition; b) 5 to 25% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) water.
22. A method for the reducing of the fading of fabrics from sunlight, comprising applying, to a previously washed article, a fabric rinse composition comprising: a) 0.1 to 10 by weight of a UV absorber of formula (1 ), based on the total weight of the composition; b) 5 to 25%, especially from 10 to 20% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) water.
23. A method according to claim 21 or 22 in which the textile article treated is composed of wool, polyamide, cotton, polyester, polyacrylic, silk or any mixture thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02706768A EP1373629A1 (en) | 2001-03-27 | 2002-03-19 | Fabric rinse composition containing a cationic uv absorber |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01810311 | 2001-03-27 | ||
EP01810311 | 2001-03-27 | ||
EP02706768A EP1373629A1 (en) | 2001-03-27 | 2002-03-19 | Fabric rinse composition containing a cationic uv absorber |
PCT/EP2002/003007 WO2002088455A1 (en) | 2001-03-27 | 2002-03-19 | Fabric rinse composition containing a cationic uv absorber |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1373629A1 true EP1373629A1 (en) | 2004-01-02 |
Family
ID=8183826
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP02706768A Withdrawn EP1373629A1 (en) | 2001-03-27 | 2002-03-19 | Fabric rinse composition containing a cationic uv absorber |
Country Status (9)
Country | Link |
---|---|
US (1) | US20040103482A1 (en) |
EP (1) | EP1373629A1 (en) |
JP (1) | JP2004526882A (en) |
KR (1) | KR20040019283A (en) |
CN (1) | CN1500167A (en) |
BR (1) | BR0208400A (en) |
CA (1) | CA2433763A1 (en) |
MX (1) | MXPA03006314A (en) |
WO (1) | WO2002088455A1 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105603743A (en) * | 2016-02-26 | 2016-05-25 | 苏州三和开泰花线织造有限公司 | Lasting efficient anti-ultraviolet finishing agent and preparation method thereof |
CN106543098B (en) * | 2016-12-07 | 2018-10-19 | 常州大学 | A kind of preparation method and applications of Mobyneb ultra-violet absorber |
CN107916569A (en) * | 2017-11-29 | 2018-04-17 | 无锡昊瑜节能环保设备有限公司 | A kind of preparation method of environment-friendly type UV resistance moisture regain looped fabric |
CN111749012B (en) * | 2020-05-21 | 2022-09-16 | 苏州浩迈纺织股份有限公司 | Water-based emulsion ultraviolet-resistant finishing agent and preparation method thereof |
CN112608467B (en) * | 2020-12-13 | 2022-09-30 | 东北石油大学 | Preparation method of cationic oil stain cleaning agent |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1567947A (en) * | 1976-07-02 | 1980-05-21 | Unilever Ltd | Esters of quaternised amino-alcohols for treating fabrics |
GB2188653A (en) * | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
US4789491A (en) * | 1987-08-07 | 1988-12-06 | The Procter & Gamble Company | Method for preparing biodegradable fabric softening compositions |
EP0357545A3 (en) * | 1988-07-21 | 1990-03-21 | Ciba-Geigy Ag | Cationic compounds, their preparation and their use in the photochemical stabilisation of basic dyeable polyamide polyacrylonitrile and polyester fibres |
US5096781A (en) * | 1988-12-19 | 1992-03-17 | Ciba-Geigy Corporation | Water-soluble compounds as light stabilizers |
GB9326358D0 (en) * | 1993-12-23 | 1994-02-23 | Ciba Geigy Ag | Compositions for the treatment of textiles |
GB2291658B (en) * | 1994-07-23 | 1998-08-12 | Ciba Geigy Ag | Aqueous textile treatment compositions containing an ultra-violet absorbing agent |
GB9602608D0 (en) * | 1996-02-09 | 1996-04-10 | Unilever Plc | Fabric softening composition |
CA2277302A1 (en) * | 1997-01-10 | 1998-07-16 | Unilever Plc | Fabric treatment compositions |
-
2002
- 2002-03-19 CA CA002433763A patent/CA2433763A1/en not_active Abandoned
- 2002-03-19 EP EP02706768A patent/EP1373629A1/en not_active Withdrawn
- 2002-03-19 CN CNA028074467A patent/CN1500167A/en active Pending
- 2002-03-19 KR KR10-2003-7012561A patent/KR20040019283A/en not_active Application Discontinuation
- 2002-03-19 WO PCT/EP2002/003007 patent/WO2002088455A1/en not_active Application Discontinuation
- 2002-03-19 JP JP2002585728A patent/JP2004526882A/en active Pending
- 2002-03-19 US US10/472,786 patent/US20040103482A1/en not_active Abandoned
- 2002-03-19 MX MXPA03006314A patent/MXPA03006314A/en unknown
- 2002-03-19 BR BR0208400-7A patent/BR0208400A/en not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO02088455A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2004526882A (en) | 2004-09-02 |
WO2002088455A1 (en) | 2002-11-07 |
BR0208400A (en) | 2004-03-30 |
CA2433763A1 (en) | 2002-11-07 |
US20040103482A1 (en) | 2004-06-03 |
KR20040019283A (en) | 2004-03-05 |
CN1500167A (en) | 2004-05-26 |
MXPA03006314A (en) | 2003-10-06 |
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