CA2348551C - Wrinkle reduction laundry product compositions - Google Patents
Wrinkle reduction laundry product compositions Download PDFInfo
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- CA2348551C CA2348551C CA002348551A CA2348551A CA2348551C CA 2348551 C CA2348551 C CA 2348551C CA 002348551 A CA002348551 A CA 002348551A CA 2348551 A CA2348551 A CA 2348551A CA 2348551 C CA2348551 C CA 2348551C
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- Prior art keywords
- clothing
- formulation
- wrinkle reducing
- wrinkle
- laundered
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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
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
- C11D3/3738—Alkoxylated silicones
-
- 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
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
- C11D3/3742—Nitrogen containing silicones
Abstract
The present application relates to the inclusion of one or more wrinkle reducing ingredients in a laundry fabric softening product. The benefits are delivered to the laundered item either during the rinse ste p of the washing procedure or in the dryer. The need for further wrinkle reducing steps when the items are taken from the dryer or after hang drying are thereby reduced. The wrinkle reducing ingredients may be chosen from ethoxylated organosilicones; polyalkyleneoxide modified polydimethylsiloxane; linear aminopolydimethylsiloxane polyalkyleneoxide copolymers; sulphated/sulphonated vegetable oils; high molecular weight polyacrylamides; betaine siloxane copolymers; and alkylactam siloxane copolymers or from wrinkle reducing compounds that d o not have a net positive charge when in neutral or alkaline medium.
Description
C'6515 (C) 4PRIN8L8 RIiDIIC'TIOa7 LACINDRY PRODUCT COMPOSITIONB
Teahnical Field The present invention relates to wrinkle reduction laundry product formulations and to methods of reducing the occurrence of wrinkles in laundered clothing.
Saekg~ and Prior Art When textiles, such as cl.othing, linens and the like, are laundered, it is typically desired that wrinkles be eliminated. or minimiz:ed after the cleaning and drying process. Mechanical wrinkle reduction techniques, such as heat and pressure (for example, ironing), have been used but can be time consuming and inconvenient.
Known attempts to reduce wrinkles by means of chemical ingredients in the wash include the use of zwitterionic surfactants, aminosiliconea, curable amirnosilicones, cei.lulase enzymes and alkyl arttides. However, each of these ingredients have one or more drawbacks. For example, zwitterionic surfactants are believed to work best in cold water. Am,in.osilicones can cause yellowing and can be difficult i_o formulate, Curable aminosilicones require the heat of an iron to reduce wrinkles. Cellulase enzymes generally require several wash cyclee before anti-wrinkle benefits become noticeable. Alkyl amides are not very effective 37elative to other wrinkle reducirxg agenta.
AMENDED SHEET
..~Na.v (4) _ 2 Liquirl fabric softeners have been sold commercially since the late 1950's. They are preferably formulated to provide softening and fragrarice benefits to fabrics (primarily cottons and cotton blends) when used in the rinse cycle of a washing machine. Liquid fabric softeners are generally formulated by making an aqueous dispersion of one or more cationic surfactants in water. The cationic purfactants are typically quarternized organonitrogen cornpounds that contain one or more, preferabl.y two, long carbon chains attached to one or more nitrogen atoms. This material provides the primary softening benefit by depositing f rom the rinee solution onto the fabrics. Additional materials typically used in these formulations include preservatives, pH control agents, viscosity modifying salts, perfumes, optical brightener:3, colourants and colour care agents.
By purchasing and using liquid fabric softeners, the consumer ie clearly interested in achieving fabric care benefits over and above those provided by known laundry detergents, Because wrinkles are generally undesirable, a liquid fabric soften.er that also decrease9 or eliminates wrinkles would be a welcomed additional benefit.
Therefore, there is a need and perceived benefit for an effective and efficient mear*s for eliminating or reducing wrinkles iri textzles. To be effective and efficient, the ingredient should preferably work across a broad range of water temperatures, nov require the use of an iron, have little to no discolcuration effect on the laundered item ar_d provide a=r.ioticeable wrinkle reducing benefit after relatively few wash cycles.
AMENDED SHEET
C y EP 009908320 Consumer products are also available that deliver softening and static control benefits in the dryer. Typically, these are in the form of fabric dryer sheets and are available under the tradenames Snuggle (Unilever) and Downy (Procter &
Gamble). While these products deliver desired benefits, additional benefits, such as wrinkle reduction, are also desirable.
Therefore, there is also a need for wrinkle reducing agents that can deliver such benefits from dryer sheets.
US-A-3992332 discloses liquid compositions for treatment of fabrics hazring silic(Dne glycol copolymer of nor_ioniC series, a phosphate: derivative of ar_ionic aeries and a compatible liquid base.
WO-A-98/56890 discloaPs odour-absorbing compositions comprising uncomplexec3 cyclodextrin and a cyclodextrin compatible wrinkle control agent.
US-A-5645751 discloses a ready-to-use fabric composition compri.sing a water-so:Luble polymer and a f:~lm-compatible silicone ironing aid/iubricant.
:25 W0-A-97/32917 discloses non-hydrolyzable block (AB)nA type copolymers comprising alternating units of polysiloxane and amine polyalkylene oxide, particularly for use in textile softeners.
:30 AMENDED SHEET
20-11-2000 C~ CA 02348551 2001-04-24 EP 009908320 RO 84337 discloses a softener composition compristng a tnono-ethanola:nine salt, ethoxylated stearin and sulphated castor oil, EP-A-544493 discloses a fabric conditioning composition, particu7.ar:ly for use in tumble dryer sheets, comprising an emulsified mixture of a silicone oil and a silicone emulsifierõ
WO-A-94/07980 discloses a fabric cleaning shampoo compoeition comprising 0,05 to 5wt% of betaine siloxane copolymer. There is :no reference to sof tening .
EP-A-025577.1 discloseb siloxane-containing fabric softening compositioris with 50wr_% to 99.9wt% of a cationic softener and 0.1 to 15wt % of the polydiorganosiloxane.
Definitioxs of the Invention Accordingly, the present invention provides in a first embodiment a liquid fabric softening formulation comprising one or more wrinkle reducing agents selected from the group consisting of: ethoxylated organosilicones;
polyalkyler..eoxide mod:_fied polydimethylsiloxanes; linear ,z5 aminopolydimethylsiloxane polyalkyleneoxide copolymers;
suiphated/sulphonated vegetable oils; betaine siloxane copolymers; and alkylactam siloxane copolymers.
The invention further provides a detergent formulation 3 0 comprising one or more quaternized organonitrogen compounds, fragrance, colourant:, water and ari effective amount of at least one wrinkle reducing agent providing a liquid fabric AMENDED SHEET
V=C.71.7 (C) softening formulation compri$ing at least one wrinkle reducing agent for reducing the occurrence of wrinkles in laundered clothing, :he at least one wrinkle reducing agent being selected from the group consisting of: ethoxylsted organosilicor_es; polyalkyleneoxide modified polydimezhylsiloxanes; linear aminopolydimethylsiJ.oxane polyalkyleneoxide copolymersj sulphated/sulphonated vegetable oils; high molecular weight polyacrylamides;
betaine si.loxane copo'lymers; and a1,Jcylactam siloxane copoiymers.
The invention further provides a liquid fabric softening formulation comprising an effective amount of a wrinkle reducirig agent for re:ducing the occurrence of wrinkles in laundered elothing, the wrinkle reducing agent being a compound that does not have a net positive charge when in an alkaline m.edium.
The invention further providee a method of reducing the occurrence of wrinkles in laundered clothing cotnprising:
i) provid.ing a liquid fabric softening formulation compr,ising at least one wrinkle reducing agent selected from the group consisting of: ethoxylated organosilicones; polyalkyleneoxide modified polyd:.meChylsiyoxanes; linear ar,-inapolydimethyl9iloxane polyalkyleneoxide copolyrners; sulphated/sulphonated vegetable oils; :betaine siloxane copoyymera; and alkylactarn siloxane coFolymers; and AMENDED SHEET
ii) contacting the formulation with clothing subsequent to a washing procedure; and iii) allowing the clothing to dry;
wherein the laundered clothing has fewer wrinkles present than clothing laundered and dried in a similar manner with a liquid softening formulation that excludes the at least one wrinkle reducing agent.
:LU The invention further provides a method of reducing the occurrence of wrinkles in laundered clothing comprising:
i) providing a liquid fabric softening formulation comprising at least one wrinkle reducing agent selected from compounds chat to do not have a net positive charge; and ii) contacting the :Eormulation with clothirig subsequent to a washing procec3Lre; and iii) allowing the cl(Dthing to dry;
wherein the lau..-~dered clothing has fewer wrinkles present than clothing laundered and dried in a similar 2,5 manner with a liquid fabric softening formulation that exclud-as the at least one wrinkle reducing agent.
The invention further provides a dryer sheet comprising a substrate and one or more wrink3.e reducing agents selected 30 from the group consisting of; ethoxylated organosilicones;
polyalkyleneoxide modified polydimethylsiloxanes; linear AMENDED SHEET
20_11_2000;c, CA 02348551 2001-04-24 EP 009908320 ami.nopolydimethylsiloxane polyalkyleneoxide copolymers;
sulphated/sulphonated vegetable oils; betaine eiloxane copolymers; and alkylactam siloxane copolymers.
The invention further provides a method of reducing the occurrence of wrinkles in laundered clothing oomprisings i) providing a dryer sheet comprising at least one wrinkle reducing agent selected form the group consisting of: ethoxylated organosilicones;
polyalkyleneoxide modified polydimethylsiloxanes;
:Linear amin.opolydimethylsiloxane polyalkyleneoxide copolyrners; sul.phatedJsulphonated vegetable oile;
betaine siloxane copolymers; and alkylactam siloxane copoLymers; and ii) contacting the dryer sheet with clothing in a drying procedure subsequent to a washing procedure;
where:in the clothing has fewer wrinkles present than clothing laundered and dried in a aimilar manner with a dryer sheet that excludes the at least one wrinkle reducing agent.
Detailed Description of the Invention The present application relates ir. one embodiment to the inclusion of one or more wrinkle reducing ingredients in a liquid faaric softe-iing product. The benefits are delivered to the Zauiidered item during the rinse step of the laundry AMENDED SHEET
20-11-2000 C} CA 02348551 2001-04-24 EP 009908320 -e -cycle (when the fabric softener is typically added) and, therefore, reduces the need for further wrinkle reducing steps when the items are taken from the dryer or after hang drying. The present application also relates to the inclusion of one or more wrinkle reducing ingredients in dryer sheets.
The ingredients that facilitate the benefit of wrinkle reduction are believed to lubricate fibre surfaces. By lubricating the fibre :aurfaces of garments, for example, the fibres slide more eas_!ly relative to each other and are less likely to entangle, resulting in less wrinkles. The preferred fibre lubricants disclosed hereiri have been shown to r.otaceably reduce the number of wrinkles. The preferred :LS embodiments also overcome or.e or more of the above noted disadvantages of prior- wrinkle reduci.ng agents or methods.
LIQL ID FABRIC SOFTENER FORN:ULATIONS
Several molecules hav-~ been identified for wrinkle reduction benefits when included. in known liquid fabric softener formulation.s. Using the American Association of Textile Chemisrs and coZorigLs (AATCC) method # 124 (described in greater detail, below), the following molecular classes were 2S found to reduce the number of wrinkles on test cloths:
ethoxylated organosilicones; polyalkyleneoxide modified polydimethylsiloxanea; linea: aminopolydimethyl.ailoxane polyalkyleneoxide copolymers; suiphated/suiphonated vegetable oils; high molecular weight polyacrylamides;
betaine siloxane copolymers; and alkylactarn siloxane copolymers. of the foregoing, the most preferred wrin)cle AMENDED SHEET
20-11-2000;C) CA 02348551 2001-04-24 EP 009908320 reducing agent is a linear ami.nopolydimethylsiloxane polyalkyleneoxide copolymer sold under the name Magnasoft SRS (available from Witco, Greenwich, CT, USA). Silsoft A-843, another aminopolydimethyleiloxane polyalkyleneoxide copolymer available from Witco, is also a particularly preferred vrinkle reducing agent. .Another preferred class of wrinkle reduction compounds are suiphated castor oils sold, for example, under the tradename Freedom SCO-75 (available from Freedom chemical Co., Charlotte, NC, USA).
One or more of the molecules/compounds from the above-identified classes are preferably included in known fabric softener formulations in an amount from 0.1 to 10 wt %, 0.1 wt t to 5 urt %, 0.3 to 1.5 wt !k and, most preferably, from 0.3 wt % to 5 wt ik. Suitable liquid fabric softener farrnulatior.Ls are described, for example, in U.S. Patent Nos.: RE 34,062 (Wells); 5,238,417 (Bauer et al.)F 5,403,499 (Kiefer et aZ.); 5,411,671 (Bauer et al); 5,460,736 (Trinh et al.) ; 5,545,350 (Bdker et al.) ; and 5,562,849 (Wahl et '20 al.) .
An additional advantacle of tne above-identified wrinkle reducing ingredients is that the molecules/compounds do not have a net positive charge in a neutral or alkaline medium, ,25 i. e. a medium having A. pH greater thari or equal to about 6.5. Lack of a net positive charge reduces the likelihood that precipitates wili reeult when the above-identified wrinkle reducfng ingredients corne in contact liquid detergents containing anionic su.rfactants, such as in the 30 rinse cycle of the laundering process. More specifically, AMENDED SHEET
20_1 1 y' 2000 ( ~,, CA 02348551 2001-04-24 EP 009908320 = . - 1Q -they are less likely to precipitate with negatively charged surfactants.
DRYER SHEET
Dryer sheets are well known in the art. They generally include a substrate, upon which active ingredients are disposed. The dryer sheet is typically added to a hot air dryer with wet clothing after a laundering cycle. The present disclosure relates to the addition of one or more wrinkle reducing agents to known dryer sheet tormulations.
The wrinkle reducing agents can be added from 0.1 wt & to 25 wt t. Hi.glzer wt k levels of wrinkle reducing agents for dryer applications are desirable because it typically takes higher wt 4 levela of active ingred=ents in the dryer, such as with dr~õrer sheets, to deliver the benefits to the same weigh-, of Labrics as compared to a rinse conditioner. in use, the dryer sheet is preferably added to a hot air clothes dryer with dai-np clothing. The sheet is allowed to come in coritact witn zhe clothing during the drying cycle.
During this cor.tact, ingredients disposed on the dryer sheet, such as the wrink-'_e reducing agents, are transferred to the clothing.
In a most preferred embodiment, the wrinkle reducing agent is a linear aminnpolyciimethylsiloxane polyalkyleneoxide copolyrner oz a 6ulph.ated castor oil. In addition, perfume is preferably added in a range from J, wt ~ to 25 wtt, preferably 1 wt* to 4 wt ~, wherein 2.5 wt t is most preferred. The fa.bric sheet formulation is applied to the aubstrate and packaged for use.
AMENDED SHEET
20-11-2000,,) CA 02348551 2001-04-24 EP 009908320 Teet Kethod A preferred method cf measuring wrinkle reduction is by using the American Association of Textile Chemists and Colorists, (AATCC) me..hod # 124, Appearance of Fabrics after Repeated Home Launder;ing. In this method=, four cloth types (silk, rayon, cotton, and linen) are washed, dried and stored in a well defined way. The dried cloths are then evaluated for wrinkle content by comlaarison with wrinkle smoothness replicas which can be purchased from AATCC.
Factors such as the light used, the angle of the cloths and replicas tc, the light, and the background are carefully controlled and described in the method. There are six 1-5 replicas with values of 1, 2, 3, 3.5, 4, and 5 with 5 being perfectly smooth and L being very wrinkled. Three trained observers are asked to give a value of 1-5, to the nearest 0.5 unit, to each cloth based on which replica it most closely resembles. The results are totalled and averaged .2 0 over the three observers for each cloth type. Aacording to the method, a difference of > 0.17 between the results for two products indicates there is a significant difference at the 95% confidence level. A difference of greater than or equal to 0.25 indicawes a significant difference at the 99*
25 confidence level.
The formulations of the invention may be prepared by any suitable method, including, the method referred to below under the table showir.ig Formula;.ion S.
_; o AMENDED SHEET
20_1 1.,2000 (C) CA 02348551 2001-04-24 EP 009908320 ,-__-Exa~tpl se The invention will be further illustrated by the following examples. Further modifications within the acope of the present ir.tvention will be apparent to the persori skilled in the art.
Formulations 1 to 5 inclusive are liquid fabri.c softener formulations. Formulation 6 is a dryer sheet fozmulation.
Formulatiou I
The following formulation containing a wrinkle reduction ingredient w3s produc:ed:
Ingredient Percent in Forrnula (by weight) Ditallow dimethyl ammonium 6.5 chloride (Arguad 2HT) Amido amine ethoxylates 17.7 (Accosoft 460) Lactic acid 0.22 Glutaraldehyde _ 0.07 Fragrance 0.7 Calcium chloride 0.2 Magnasoft SRS+ 0.5 Colourants (ppm) Water to 100%
*Wrinkle reducticn agent - a linear aminopolyt3imethylsiloxane polyalkyleneoxide copolymer from Witco Cheinical Co.
AMENDED SHEET
20-11 -' 2000 , \ CA 02348551 2001-04-24 EP 009908320 40J1:7 (`J
Formulatioa 2: The same as formulation I without the k=rinkle reduction agent present, Laboratory tests have shown wrinkle reduction benefits for Formulation 1 are greater than that of Formulation 2.
Wrinkle Test Results Using the AATCC fabric smoothness test method as described above, several fabric types were laundered using either formulation 1 with Magna$oft SRS at 0.5-W or the same formulatioil without any wrinkle reduction additive (Formulation 2). Res=slts of the testing after four laundering cycles show wrinkle reduction benefits with use of Magnasoft SRS (Formulation 1) on rayon, siZk, linen and 100% cottori. The resu'lts are significant at the 95;r confidence level.
Fabric Smoothness Scores Silk Rayon Linen Cotton Forrn. 1 3.28 2.11 2.72 2.20 Form. 2 3.00 1.78 2.28 1.89 The following are other preferred forrnulations containing at least one wrinkle red;:ci:g agent :
AMENDED SHEET
...,.._.. tC) Forvulation 3 Ingredient Pereent in Formula (by wei ht ) Ditallow dimethyl ammoniurn 6.5 chloride ( Ar ad 2:EiT ) Ami3o arni.ne ethoxylates 17.7 (Accosoft 460) Lactic acid 0.22 Glutaraldehyde 0.07 Fragrance 0.7 Calcium chloride 0.2 Ma nasoft SRSw 3.0 Colour. ant;3 (ppm) Water to 100%
* Wrinkle reduction agent - a linear aminopolydimethvlsiloxane polyalkyleneoxide copolymer from Witco Chermical Co.
Forxmulation 4 Ir.gredi~ent: Percent in Fortnul-a (by weight) Ditallow dimethyl amzror.ium 6.5 chloride (Ar ad 2HT) Amido amirLe ethoxyla~:eE 17.7 (ACcosoft 460) Lactic acid 0.22 Glutaraldehyde 0.07 Fragrance 0,' Calcium chloride 0.2 Freedom SC:O-7,x 1.0%
Colourants (p~m1 Water to 100%
* Wrinkle reduction agent - a sulphated castor oil from Freedom Chemical Company.
AMENDED SHEET
20_11_2000 C) CA 02348551 2001-04-24 EP 009908320 For=iatioa 5 Ingredient Percent in Formula (by _ weight) Ditallow dimethyl ammonium 6.5 chloride (Axquad 2HT) Amido amine ethoxylates 17.7 (Accosoft 460) Lactic acid 0,22 Glutaraldeh de 0.07 Fragrance _ 0.7 Calcium chloride 0.2 Freedom SC'0-75* 4,0-t Colourants (ppm) Water to l0oW
* Wrinkle reduction agent - a sulphated castor oil from Freedom Chemical Company.
Preferred Method of Formula Preparation The above cited formulas were prepared as follows: The quaternary fabric softener actives were mixed together under moderate agitation and heated to 160 degrees F
(approximately 71 C). The water and some minor ingredients (colourants and preservatives) were combined in a second mixing vessel and were also heated to 160 degrees F
(approximately 71 C). The two mixes were then combined by addition of the actives premix to the main batch under vi3orous agitation. Viscosity control salts were added to the mixture in several inorements while the batch was cooled .>.0 to 100 degrees F(approximately 38 C). The fragrance and the wrinkle red=,iction conlpounds were then added under moderate AMENDED SHEET
20-11-2000:C) CA 02348551 2001-04-24 EP 009908320 -is-agitation and the batch was further cooled to room temperature. The resultant product war uniform and free flowing and remained stable and pcurable over time, Formulatiou 6 Forjauiation for a Dryer Sheet Ingredient Percent in Formula (by _ h~ei ht) Free Fatty Acid 46.8 Wrinkle reducing agent 10 Nonionic Surfactant 22.5 Potassium Soap 16.2 Water 4.5 The above example presents a formulation having 10 wt %
wrinkle reducing ag"t for a dryer aheet:
All component percentages herein are by weight based upon the total weight of the compcsl'Lion, unless otherwise indicated..
AMENDED SHEET
Teahnical Field The present invention relates to wrinkle reduction laundry product formulations and to methods of reducing the occurrence of wrinkles in laundered clothing.
Saekg~ and Prior Art When textiles, such as cl.othing, linens and the like, are laundered, it is typically desired that wrinkles be eliminated. or minimiz:ed after the cleaning and drying process. Mechanical wrinkle reduction techniques, such as heat and pressure (for example, ironing), have been used but can be time consuming and inconvenient.
Known attempts to reduce wrinkles by means of chemical ingredients in the wash include the use of zwitterionic surfactants, aminosiliconea, curable amirnosilicones, cei.lulase enzymes and alkyl arttides. However, each of these ingredients have one or more drawbacks. For example, zwitterionic surfactants are believed to work best in cold water. Am,in.osilicones can cause yellowing and can be difficult i_o formulate, Curable aminosilicones require the heat of an iron to reduce wrinkles. Cellulase enzymes generally require several wash cyclee before anti-wrinkle benefits become noticeable. Alkyl amides are not very effective 37elative to other wrinkle reducirxg agenta.
AMENDED SHEET
..~Na.v (4) _ 2 Liquirl fabric softeners have been sold commercially since the late 1950's. They are preferably formulated to provide softening and fragrarice benefits to fabrics (primarily cottons and cotton blends) when used in the rinse cycle of a washing machine. Liquid fabric softeners are generally formulated by making an aqueous dispersion of one or more cationic surfactants in water. The cationic purfactants are typically quarternized organonitrogen cornpounds that contain one or more, preferabl.y two, long carbon chains attached to one or more nitrogen atoms. This material provides the primary softening benefit by depositing f rom the rinee solution onto the fabrics. Additional materials typically used in these formulations include preservatives, pH control agents, viscosity modifying salts, perfumes, optical brightener:3, colourants and colour care agents.
By purchasing and using liquid fabric softeners, the consumer ie clearly interested in achieving fabric care benefits over and above those provided by known laundry detergents, Because wrinkles are generally undesirable, a liquid fabric soften.er that also decrease9 or eliminates wrinkles would be a welcomed additional benefit.
Therefore, there is a need and perceived benefit for an effective and efficient mear*s for eliminating or reducing wrinkles iri textzles. To be effective and efficient, the ingredient should preferably work across a broad range of water temperatures, nov require the use of an iron, have little to no discolcuration effect on the laundered item ar_d provide a=r.ioticeable wrinkle reducing benefit after relatively few wash cycles.
AMENDED SHEET
C y EP 009908320 Consumer products are also available that deliver softening and static control benefits in the dryer. Typically, these are in the form of fabric dryer sheets and are available under the tradenames Snuggle (Unilever) and Downy (Procter &
Gamble). While these products deliver desired benefits, additional benefits, such as wrinkle reduction, are also desirable.
Therefore, there is also a need for wrinkle reducing agents that can deliver such benefits from dryer sheets.
US-A-3992332 discloses liquid compositions for treatment of fabrics hazring silic(Dne glycol copolymer of nor_ioniC series, a phosphate: derivative of ar_ionic aeries and a compatible liquid base.
WO-A-98/56890 discloaPs odour-absorbing compositions comprising uncomplexec3 cyclodextrin and a cyclodextrin compatible wrinkle control agent.
US-A-5645751 discloses a ready-to-use fabric composition compri.sing a water-so:Luble polymer and a f:~lm-compatible silicone ironing aid/iubricant.
:25 W0-A-97/32917 discloses non-hydrolyzable block (AB)nA type copolymers comprising alternating units of polysiloxane and amine polyalkylene oxide, particularly for use in textile softeners.
:30 AMENDED SHEET
20-11-2000 C~ CA 02348551 2001-04-24 EP 009908320 RO 84337 discloses a softener composition compristng a tnono-ethanola:nine salt, ethoxylated stearin and sulphated castor oil, EP-A-544493 discloses a fabric conditioning composition, particu7.ar:ly for use in tumble dryer sheets, comprising an emulsified mixture of a silicone oil and a silicone emulsifierõ
WO-A-94/07980 discloses a fabric cleaning shampoo compoeition comprising 0,05 to 5wt% of betaine siloxane copolymer. There is :no reference to sof tening .
EP-A-025577.1 discloseb siloxane-containing fabric softening compositioris with 50wr_% to 99.9wt% of a cationic softener and 0.1 to 15wt % of the polydiorganosiloxane.
Definitioxs of the Invention Accordingly, the present invention provides in a first embodiment a liquid fabric softening formulation comprising one or more wrinkle reducing agents selected from the group consisting of: ethoxylated organosilicones;
polyalkyler..eoxide mod:_fied polydimethylsiloxanes; linear ,z5 aminopolydimethylsiloxane polyalkyleneoxide copolymers;
suiphated/sulphonated vegetable oils; betaine siloxane copolymers; and alkylactam siloxane copolymers.
The invention further provides a detergent formulation 3 0 comprising one or more quaternized organonitrogen compounds, fragrance, colourant:, water and ari effective amount of at least one wrinkle reducing agent providing a liquid fabric AMENDED SHEET
V=C.71.7 (C) softening formulation compri$ing at least one wrinkle reducing agent for reducing the occurrence of wrinkles in laundered clothing, :he at least one wrinkle reducing agent being selected from the group consisting of: ethoxylsted organosilicor_es; polyalkyleneoxide modified polydimezhylsiloxanes; linear aminopolydimethylsiJ.oxane polyalkyleneoxide copolymersj sulphated/sulphonated vegetable oils; high molecular weight polyacrylamides;
betaine si.loxane copo'lymers; and a1,Jcylactam siloxane copoiymers.
The invention further provides a liquid fabric softening formulation comprising an effective amount of a wrinkle reducirig agent for re:ducing the occurrence of wrinkles in laundered elothing, the wrinkle reducing agent being a compound that does not have a net positive charge when in an alkaline m.edium.
The invention further providee a method of reducing the occurrence of wrinkles in laundered clothing cotnprising:
i) provid.ing a liquid fabric softening formulation compr,ising at least one wrinkle reducing agent selected from the group consisting of: ethoxylated organosilicones; polyalkyleneoxide modified polyd:.meChylsiyoxanes; linear ar,-inapolydimethyl9iloxane polyalkyleneoxide copolyrners; sulphated/sulphonated vegetable oils; :betaine siloxane copoyymera; and alkylactarn siloxane coFolymers; and AMENDED SHEET
ii) contacting the formulation with clothing subsequent to a washing procedure; and iii) allowing the clothing to dry;
wherein the laundered clothing has fewer wrinkles present than clothing laundered and dried in a similar manner with a liquid softening formulation that excludes the at least one wrinkle reducing agent.
:LU The invention further provides a method of reducing the occurrence of wrinkles in laundered clothing comprising:
i) providing a liquid fabric softening formulation comprising at least one wrinkle reducing agent selected from compounds chat to do not have a net positive charge; and ii) contacting the :Eormulation with clothirig subsequent to a washing procec3Lre; and iii) allowing the cl(Dthing to dry;
wherein the lau..-~dered clothing has fewer wrinkles present than clothing laundered and dried in a similar 2,5 manner with a liquid fabric softening formulation that exclud-as the at least one wrinkle reducing agent.
The invention further provides a dryer sheet comprising a substrate and one or more wrink3.e reducing agents selected 30 from the group consisting of; ethoxylated organosilicones;
polyalkyleneoxide modified polydimethylsiloxanes; linear AMENDED SHEET
20_11_2000;c, CA 02348551 2001-04-24 EP 009908320 ami.nopolydimethylsiloxane polyalkyleneoxide copolymers;
sulphated/sulphonated vegetable oils; betaine eiloxane copolymers; and alkylactam siloxane copolymers.
The invention further provides a method of reducing the occurrence of wrinkles in laundered clothing oomprisings i) providing a dryer sheet comprising at least one wrinkle reducing agent selected form the group consisting of: ethoxylated organosilicones;
polyalkyleneoxide modified polydimethylsiloxanes;
:Linear amin.opolydimethylsiloxane polyalkyleneoxide copolyrners; sul.phatedJsulphonated vegetable oile;
betaine siloxane copolymers; and alkylactam siloxane copoLymers; and ii) contacting the dryer sheet with clothing in a drying procedure subsequent to a washing procedure;
where:in the clothing has fewer wrinkles present than clothing laundered and dried in a aimilar manner with a dryer sheet that excludes the at least one wrinkle reducing agent.
Detailed Description of the Invention The present application relates ir. one embodiment to the inclusion of one or more wrinkle reducing ingredients in a liquid faaric softe-iing product. The benefits are delivered to the Zauiidered item during the rinse step of the laundry AMENDED SHEET
20-11-2000 C} CA 02348551 2001-04-24 EP 009908320 -e -cycle (when the fabric softener is typically added) and, therefore, reduces the need for further wrinkle reducing steps when the items are taken from the dryer or after hang drying. The present application also relates to the inclusion of one or more wrinkle reducing ingredients in dryer sheets.
The ingredients that facilitate the benefit of wrinkle reduction are believed to lubricate fibre surfaces. By lubricating the fibre :aurfaces of garments, for example, the fibres slide more eas_!ly relative to each other and are less likely to entangle, resulting in less wrinkles. The preferred fibre lubricants disclosed hereiri have been shown to r.otaceably reduce the number of wrinkles. The preferred :LS embodiments also overcome or.e or more of the above noted disadvantages of prior- wrinkle reduci.ng agents or methods.
LIQL ID FABRIC SOFTENER FORN:ULATIONS
Several molecules hav-~ been identified for wrinkle reduction benefits when included. in known liquid fabric softener formulation.s. Using the American Association of Textile Chemisrs and coZorigLs (AATCC) method # 124 (described in greater detail, below), the following molecular classes were 2S found to reduce the number of wrinkles on test cloths:
ethoxylated organosilicones; polyalkyleneoxide modified polydimethylsiloxanea; linea: aminopolydimethyl.ailoxane polyalkyleneoxide copolymers; suiphated/suiphonated vegetable oils; high molecular weight polyacrylamides;
betaine siloxane copolymers; and alkylactarn siloxane copolymers. of the foregoing, the most preferred wrin)cle AMENDED SHEET
20-11-2000;C) CA 02348551 2001-04-24 EP 009908320 reducing agent is a linear ami.nopolydimethylsiloxane polyalkyleneoxide copolymer sold under the name Magnasoft SRS (available from Witco, Greenwich, CT, USA). Silsoft A-843, another aminopolydimethyleiloxane polyalkyleneoxide copolymer available from Witco, is also a particularly preferred vrinkle reducing agent. .Another preferred class of wrinkle reduction compounds are suiphated castor oils sold, for example, under the tradename Freedom SCO-75 (available from Freedom chemical Co., Charlotte, NC, USA).
One or more of the molecules/compounds from the above-identified classes are preferably included in known fabric softener formulations in an amount from 0.1 to 10 wt %, 0.1 wt t to 5 urt %, 0.3 to 1.5 wt !k and, most preferably, from 0.3 wt % to 5 wt ik. Suitable liquid fabric softener farrnulatior.Ls are described, for example, in U.S. Patent Nos.: RE 34,062 (Wells); 5,238,417 (Bauer et al.)F 5,403,499 (Kiefer et aZ.); 5,411,671 (Bauer et al); 5,460,736 (Trinh et al.) ; 5,545,350 (Bdker et al.) ; and 5,562,849 (Wahl et '20 al.) .
An additional advantacle of tne above-identified wrinkle reducing ingredients is that the molecules/compounds do not have a net positive charge in a neutral or alkaline medium, ,25 i. e. a medium having A. pH greater thari or equal to about 6.5. Lack of a net positive charge reduces the likelihood that precipitates wili reeult when the above-identified wrinkle reducfng ingredients corne in contact liquid detergents containing anionic su.rfactants, such as in the 30 rinse cycle of the laundering process. More specifically, AMENDED SHEET
20_1 1 y' 2000 ( ~,, CA 02348551 2001-04-24 EP 009908320 = . - 1Q -they are less likely to precipitate with negatively charged surfactants.
DRYER SHEET
Dryer sheets are well known in the art. They generally include a substrate, upon which active ingredients are disposed. The dryer sheet is typically added to a hot air dryer with wet clothing after a laundering cycle. The present disclosure relates to the addition of one or more wrinkle reducing agents to known dryer sheet tormulations.
The wrinkle reducing agents can be added from 0.1 wt & to 25 wt t. Hi.glzer wt k levels of wrinkle reducing agents for dryer applications are desirable because it typically takes higher wt 4 levela of active ingred=ents in the dryer, such as with dr~õrer sheets, to deliver the benefits to the same weigh-, of Labrics as compared to a rinse conditioner. in use, the dryer sheet is preferably added to a hot air clothes dryer with dai-np clothing. The sheet is allowed to come in coritact witn zhe clothing during the drying cycle.
During this cor.tact, ingredients disposed on the dryer sheet, such as the wrink-'_e reducing agents, are transferred to the clothing.
In a most preferred embodiment, the wrinkle reducing agent is a linear aminnpolyciimethylsiloxane polyalkyleneoxide copolyrner oz a 6ulph.ated castor oil. In addition, perfume is preferably added in a range from J, wt ~ to 25 wtt, preferably 1 wt* to 4 wt ~, wherein 2.5 wt t is most preferred. The fa.bric sheet formulation is applied to the aubstrate and packaged for use.
AMENDED SHEET
20-11-2000,,) CA 02348551 2001-04-24 EP 009908320 Teet Kethod A preferred method cf measuring wrinkle reduction is by using the American Association of Textile Chemists and Colorists, (AATCC) me..hod # 124, Appearance of Fabrics after Repeated Home Launder;ing. In this method=, four cloth types (silk, rayon, cotton, and linen) are washed, dried and stored in a well defined way. The dried cloths are then evaluated for wrinkle content by comlaarison with wrinkle smoothness replicas which can be purchased from AATCC.
Factors such as the light used, the angle of the cloths and replicas tc, the light, and the background are carefully controlled and described in the method. There are six 1-5 replicas with values of 1, 2, 3, 3.5, 4, and 5 with 5 being perfectly smooth and L being very wrinkled. Three trained observers are asked to give a value of 1-5, to the nearest 0.5 unit, to each cloth based on which replica it most closely resembles. The results are totalled and averaged .2 0 over the three observers for each cloth type. Aacording to the method, a difference of > 0.17 between the results for two products indicates there is a significant difference at the 95% confidence level. A difference of greater than or equal to 0.25 indicawes a significant difference at the 99*
25 confidence level.
The formulations of the invention may be prepared by any suitable method, including, the method referred to below under the table showir.ig Formula;.ion S.
_; o AMENDED SHEET
20_1 1.,2000 (C) CA 02348551 2001-04-24 EP 009908320 ,-__-Exa~tpl se The invention will be further illustrated by the following examples. Further modifications within the acope of the present ir.tvention will be apparent to the persori skilled in the art.
Formulations 1 to 5 inclusive are liquid fabri.c softener formulations. Formulation 6 is a dryer sheet fozmulation.
Formulatiou I
The following formulation containing a wrinkle reduction ingredient w3s produc:ed:
Ingredient Percent in Forrnula (by weight) Ditallow dimethyl ammonium 6.5 chloride (Arguad 2HT) Amido amine ethoxylates 17.7 (Accosoft 460) Lactic acid 0.22 Glutaraldehyde _ 0.07 Fragrance 0.7 Calcium chloride 0.2 Magnasoft SRS+ 0.5 Colourants (ppm) Water to 100%
*Wrinkle reducticn agent - a linear aminopolyt3imethylsiloxane polyalkyleneoxide copolymer from Witco Cheinical Co.
AMENDED SHEET
20-11 -' 2000 , \ CA 02348551 2001-04-24 EP 009908320 40J1:7 (`J
Formulatioa 2: The same as formulation I without the k=rinkle reduction agent present, Laboratory tests have shown wrinkle reduction benefits for Formulation 1 are greater than that of Formulation 2.
Wrinkle Test Results Using the AATCC fabric smoothness test method as described above, several fabric types were laundered using either formulation 1 with Magna$oft SRS at 0.5-W or the same formulatioil without any wrinkle reduction additive (Formulation 2). Res=slts of the testing after four laundering cycles show wrinkle reduction benefits with use of Magnasoft SRS (Formulation 1) on rayon, siZk, linen and 100% cottori. The resu'lts are significant at the 95;r confidence level.
Fabric Smoothness Scores Silk Rayon Linen Cotton Forrn. 1 3.28 2.11 2.72 2.20 Form. 2 3.00 1.78 2.28 1.89 The following are other preferred forrnulations containing at least one wrinkle red;:ci:g agent :
AMENDED SHEET
...,.._.. tC) Forvulation 3 Ingredient Pereent in Formula (by wei ht ) Ditallow dimethyl ammoniurn 6.5 chloride ( Ar ad 2:EiT ) Ami3o arni.ne ethoxylates 17.7 (Accosoft 460) Lactic acid 0.22 Glutaraldehyde 0.07 Fragrance 0.7 Calcium chloride 0.2 Ma nasoft SRSw 3.0 Colour. ant;3 (ppm) Water to 100%
* Wrinkle reduction agent - a linear aminopolydimethvlsiloxane polyalkyleneoxide copolymer from Witco Chermical Co.
Forxmulation 4 Ir.gredi~ent: Percent in Fortnul-a (by weight) Ditallow dimethyl amzror.ium 6.5 chloride (Ar ad 2HT) Amido amirLe ethoxyla~:eE 17.7 (ACcosoft 460) Lactic acid 0.22 Glutaraldehyde 0.07 Fragrance 0,' Calcium chloride 0.2 Freedom SC:O-7,x 1.0%
Colourants (p~m1 Water to 100%
* Wrinkle reduction agent - a sulphated castor oil from Freedom Chemical Company.
AMENDED SHEET
20_11_2000 C) CA 02348551 2001-04-24 EP 009908320 For=iatioa 5 Ingredient Percent in Formula (by _ weight) Ditallow dimethyl ammonium 6.5 chloride (Axquad 2HT) Amido amine ethoxylates 17.7 (Accosoft 460) Lactic acid 0,22 Glutaraldeh de 0.07 Fragrance _ 0.7 Calcium chloride 0.2 Freedom SC'0-75* 4,0-t Colourants (ppm) Water to l0oW
* Wrinkle reduction agent - a sulphated castor oil from Freedom Chemical Company.
Preferred Method of Formula Preparation The above cited formulas were prepared as follows: The quaternary fabric softener actives were mixed together under moderate agitation and heated to 160 degrees F
(approximately 71 C). The water and some minor ingredients (colourants and preservatives) were combined in a second mixing vessel and were also heated to 160 degrees F
(approximately 71 C). The two mixes were then combined by addition of the actives premix to the main batch under vi3orous agitation. Viscosity control salts were added to the mixture in several inorements while the batch was cooled .>.0 to 100 degrees F(approximately 38 C). The fragrance and the wrinkle red=,iction conlpounds were then added under moderate AMENDED SHEET
20-11-2000:C) CA 02348551 2001-04-24 EP 009908320 -is-agitation and the batch was further cooled to room temperature. The resultant product war uniform and free flowing and remained stable and pcurable over time, Formulatiou 6 Forjauiation for a Dryer Sheet Ingredient Percent in Formula (by _ h~ei ht) Free Fatty Acid 46.8 Wrinkle reducing agent 10 Nonionic Surfactant 22.5 Potassium Soap 16.2 Water 4.5 The above example presents a formulation having 10 wt %
wrinkle reducing ag"t for a dryer aheet:
All component percentages herein are by weight based upon the total weight of the compcsl'Lion, unless otherwise indicated..
AMENDED SHEET
Claims (7)
1. A method of reducing the occurrence of wrinkles in laundered clothing comprising:
i) providing a liquid fabric softening formulation comprising at least one wrinkle reducing agent selected from the group consisting of: ethoxylated organosilicones; polyalkyleneoxide modified polydimethylsiloxane; linear aminopolydimethylsiloxane polyalkyleneoxide copolymers; sulphated/sulphonated vegetable oils; betaine siloxane copolymers; and alkylactam siloxane copolymers; and a cationic fabric softening compound; and ii) contacting the formulation with clothing subsequent to a washing procedure; and iii) allowing the clothing to dry;
wherein the laundered clothing has fewer wrinkles present than clothing laundered and dried in a similar manner with a liquid softening formulation that excludes the at least one wrinkle reducing agent.
i) providing a liquid fabric softening formulation comprising at least one wrinkle reducing agent selected from the group consisting of: ethoxylated organosilicones; polyalkyleneoxide modified polydimethylsiloxane; linear aminopolydimethylsiloxane polyalkyleneoxide copolymers; sulphated/sulphonated vegetable oils; betaine siloxane copolymers; and alkylactam siloxane copolymers; and a cationic fabric softening compound; and ii) contacting the formulation with clothing subsequent to a washing procedure; and iii) allowing the clothing to dry;
wherein the laundered clothing has fewer wrinkles present than clothing laundered and dried in a similar manner with a liquid softening formulation that excludes the at least one wrinkle reducing agent.
2. A method of reducing the occurrence of wrinkles in laundered clothing comprising:
i) providing a liquid fabric softening formulation comprising at least one wrinkle reducing agent selected from compounds that to do not have a net positive charge in a neutral or alkaline medium;
and ii) contacting the formulation with clothing subsequent to a washing procedure; and iii) allowing the clothing to dry; wherein the laundered clothing has fewer wrinkles present than clothing laundered and dried in a similar manner with a liquid fabric softening formulation that excludes the at least one wrinkle reducing agent.
i) providing a liquid fabric softening formulation comprising at least one wrinkle reducing agent selected from compounds that to do not have a net positive charge in a neutral or alkaline medium;
and ii) contacting the formulation with clothing subsequent to a washing procedure; and iii) allowing the clothing to dry; wherein the laundered clothing has fewer wrinkles present than clothing laundered and dried in a similar manner with a liquid fabric softening formulation that excludes the at least one wrinkle reducing agent.
3. A method of reducing the occurrence of wrinkles in laundered clothing comprising:
i) providing a dryer sheet comprising at least one wrinkle reducing agent selected from the group consisting of: ethoxylated organosilicones;
polyalkyleneoxide modified polydimethylsiloxanes;
linear aminopolydimethylsiloxane polyalkyleneoxide copolymers; sulphated/sulphonated vegetable oils;
betaine siloxane copolymers; and alkylactam siloxane copolymers; and ii) contacting the dryer sheet with clothing in a drying procedure subsequent to a washing procedure;
wherein the clothing has fewer wrinkles present than clothing laundered and dried in a similar manner with a dryer sheet that excludes the at least one wrinkle reducing agent.
i) providing a dryer sheet comprising at least one wrinkle reducing agent selected from the group consisting of: ethoxylated organosilicones;
polyalkyleneoxide modified polydimethylsiloxanes;
linear aminopolydimethylsiloxane polyalkyleneoxide copolymers; sulphated/sulphonated vegetable oils;
betaine siloxane copolymers; and alkylactam siloxane copolymers; and ii) contacting the dryer sheet with clothing in a drying procedure subsequent to a washing procedure;
wherein the clothing has fewer wrinkles present than clothing laundered and dried in a similar manner with a dryer sheet that excludes the at least one wrinkle reducing agent.
4. A method according to either claim 1 or claim 2, wherein at least one of the wrinkle reducing agents is present in the formulation in an amount from 0.1 wt% to wt% of the formulation.
5. A method according to either claim 1 or claim 2 wherein at least one of the wrinkle reducing agents is present in the formulation in an amount from 0.5 wt% to 3.0 wt%
of the formulation.
of the formulation.
6. A method according to claim 3 wherein at least one of the wrinkle reducing agents is present in an amount from 0.1 wt% to 25 wt% of a dryer sheet formulation.
7. A -method according to any one of claims 1 to 6 wherein the wrinkle reducing agent is a linear aminopolydimethylsiloxane polyalkyleneoxide copolymer or a sulphated caster oil.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10588798P | 1998-10-27 | 1998-10-27 | |
| US60/105,887 | 1998-10-27 | ||
| US09/293,323 | 1999-04-16 | ||
| US09/293,323 US6376456B1 (en) | 1998-10-27 | 1999-04-16 | Wrinkle reduction laundry product compositions |
| PCT/EP1999/008320 WO2000024853A2 (en) | 1998-10-27 | 1999-10-21 | Wrinkle reduction laundry product compositions |
Publications (2)
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|---|---|
| CA2348551A1 CA2348551A1 (en) | 2000-05-04 |
| CA2348551C true CA2348551C (en) | 2009-12-15 |
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|---|---|---|---|
| CA002348551A Expired - Lifetime CA2348551C (en) | 1998-10-27 | 1999-10-21 | Wrinkle reduction laundry product compositions |
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| US (1) | US6376456B1 (en) |
| EP (1) | EP1124925B1 (en) |
| AR (1) | AR023910A1 (en) |
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| CA (1) | CA2348551C (en) |
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| ES (1) | ES2214063T3 (en) |
| ID (1) | ID29018A (en) |
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-
1999
- 1999-04-16 US US09/293,323 patent/US6376456B1/en not_active Expired - Lifetime
- 1999-10-21 WO PCT/EP1999/008320 patent/WO2000024853A2/en active IP Right Grant
- 1999-10-21 AT AT99971023T patent/ATE258219T1/en not_active IP Right Cessation
- 1999-10-21 ID IDW20010922A patent/ID29018A/en unknown
- 1999-10-21 CA CA002348551A patent/CA2348551C/en not_active Expired - Lifetime
- 1999-10-21 ES ES99971023T patent/ES2214063T3/en not_active Expired - Lifetime
- 1999-10-21 EP EP99971023A patent/EP1124925B1/en not_active Expired - Lifetime
- 1999-10-21 BR BRPI9914852-8A patent/BR9914852B1/en not_active IP Right Cessation
- 1999-10-21 DE DE69914353T patent/DE69914353T2/en not_active Expired - Lifetime
- 1999-10-21 AU AU11586/00A patent/AU1158600A/en not_active Abandoned
- 1999-10-27 AR ARP990105410A patent/AR023910A1/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| DE69914353D1 (en) | 2004-02-26 |
| AU1158600A (en) | 2000-05-15 |
| CA2348551A1 (en) | 2000-05-04 |
| BR9914852B1 (en) | 2008-11-18 |
| WO2000024853A3 (en) | 2000-08-10 |
| US6376456B1 (en) | 2002-04-23 |
| ATE258219T1 (en) | 2004-02-15 |
| ES2214063T3 (en) | 2004-09-01 |
| BR9914852A (en) | 2001-07-03 |
| ID29018A (en) | 2001-07-26 |
| WO2000024853A2 (en) | 2000-05-04 |
| EP1124925A2 (en) | 2001-08-22 |
| EP1124925B1 (en) | 2004-01-21 |
| AR023910A1 (en) | 2002-09-04 |
| DE69914353T2 (en) | 2004-07-01 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20191021 |