WO1996015309A2 - Wrinkle reducing composition - Google Patents

Wrinkle reducing composition Download PDF

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Publication number
WO1996015309A2
WO1996015309A2 PCT/US1995/014030 US9514030W WO9615309A2 WO 1996015309 A2 WO1996015309 A2 WO 1996015309A2 US 9514030 W US9514030 W US 9514030W WO 9615309 A2 WO9615309 A2 WO 9615309A2
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WO
WIPO (PCT)
Prior art keywords
composition
vinyl
wrinkle reducing
fabric
silicone
Prior art date
Application number
PCT/US1995/014030
Other languages
English (en)
French (fr)
Other versions
WO1996015309A3 (en
Inventor
Alice Marie Vogel
Errol Hoffman Wahl
Jerome Paul Cappel
Thomas Carl Ward
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP8516102A priority Critical patent/JPH10508911A/ja
Priority to MX9703522A priority patent/MX9703522A/es
Priority to BR9509712A priority patent/BR9509712A/pt
Priority to CA002205025A priority patent/CA2205025C/en
Priority to EP95939646A priority patent/EP0791097A2/en
Publication of WO1996015309A2 publication Critical patent/WO1996015309A2/en
Publication of WO1996015309A3 publication Critical patent/WO1996015309A3/en

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/02Processes in which the treating agent is releasably affixed or incorporated into a dispensing means
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144Alcohols; Metal alcoholates
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/463Compounds containing quaternary nitrogen atoms derived from monoamines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/06Processes in which the treating agent is dispersed in a gas, e.g. aerosols
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/20Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease

Definitions

  • the present invention relates to fabric care compositions and to a method for treating fabrics in order to improve various properties of fabrics, in particular, reduction or removal of unwanted wrinkles.
  • the present invention reduces wrinkles from fabrics, including clothing, dry cleanables, and draperies, without the need for ironing.
  • the present invention can be used on damp or dry clothing to relax wrinkles and give clothes a ready to wear look that is demanded by today's fast paced world.
  • the present invention also essentially eliminates the need for touch up ironing usually associated with closet, drawer, and suitcase storage of garments.
  • the present invention can also act as an excellent ironing aid.
  • the present invention makes the task of ironing easier and faster by creating less iron drag.
  • the composition of the present invention produces a crisp, smooth appearance similar to that of spray starch ironing aids without the dry residue or flaking that occurs with typical spray starch ironing aids a n additional benefit of the composition of the present invention is an in- wear wrinkle control benefit.
  • the composition of the present invention can help to prevent future wrinkles from forming in the fabric even after the fabric has been through a wash cycle.
  • the present invention relates to a wrinkle reducing composition, comprising:
  • a wrinkle reducing active comprising: 1. an effective amount of silicone;
  • the present invention relates to a wrinkle reducing composition, comprising:
  • a a wrinkle reducing active comprising:
  • the present invention in one aspect, uses silicone to impart a lubricating property or increased gliding ability to fibers in fabric, particularly clothing.
  • silicone any type of silicone can be used to impart the lubricating property of the present invention however, some silicones and mixtures of silicones are more preferred.
  • silicone refers to emulsified silicones, including those that are commercially available and those that are emulsified in the composition, unless otherwise described.
  • Some non-limiting examples of silicones which are useful in the present invention are: Non-volatile silicone fluids such as polydimethylsiloxane gums and fluids, aminosilicones, reactive silicones and - j - phenylsilicones More specifically, materials such as polyalkyl or polyaryl silicones with the following structu
  • the alkyl or aryl groups substituted on the siloxane chain (R) or at the ends of the siloxane chains (A) can have any structure as long as the resulting silicones remain fluid at room temperature.
  • the silicones are hydrophobic, are neither irritating, toxic, nor otherwise harmful when applied to fabric or when they come in contact with human skin, are compatible with other components of the composition, are chemically stable under normal use and storage conditions, and are capable of being deposited on fabric.
  • the R group preferably is a phenyl, a hydroxy, an alkyl or an aryl.
  • R groups on the silicone atom can represent the same group or different groups.
  • the two R groups represent the same group preferably, a methyl, an ethyl, a propyl, a phenyl or a hydroxy group, q is preferably an integer from about 7 to about 8,000.
  • A represents groups which block the ends of the silicone chains. Suitable A groups include hydrogen, methyl, methoxy, ethoxy, hydroxy, propoxy, and aryloxy.
  • the preferred silicones are polydimethyl siloxanes; more preferred silicones are polydimethyl siloxanes having a viscosity of greater than about 10,000 centistokes (cst) at 25°C; and a most preferred silicone is a reactive silicone, i.e., where A is an OH group.
  • Suitable methods for preparing these silicone materials are disclosed in U.S. Pat. Nos. 2,826,551 and 3,964,500, incorporated herein by reference. Silicones useful in the present invention are also commercially available. Suitable examples include silicones offered by Dow Corning Corporation.
  • silicone materials include materials of the formula: wherein x and y are integers which depend on the molecular weight of the silicone, the viscosity being from about 10,000 (cst) to about 500,000 (cst) at 25°C. This material is also known as "amodimethicone". Although silicones with a high number, e.g., greater than about 0.5 millimolar equivalent of amine groups can be used, they are not preferred because they can cause fabric yellowing.
  • G is selected from the group consisting of hydrogen, phenyl, OH, and/or C ⁇ - Cg alkyl; a denotes 0 or an integer from 1 to 3; b denotes 0 or 1; the sum of n + m is a number from 1 to about 2,000; R s a monovalent radical of formula C p H 2p L in which p is an integer from 2 to 8 and L is selected from the group consisting of: -N(R 2 )CH 2 -CH 2 -N(R 2 ) 2 ; -N(R 2 ) 2 ;
  • each R 2 is chosen from the group consisting of hydrogen, phenyl, benzyl, a saturated hydrocarbon radical, and each A" denotes compatible anion, e.g., a halide ion;
  • R3 denotes a long chain alkyl group; and f denotes an integer of at least about 2.
  • Another silicone material which can be used, but is not preferred, has the formula:
  • n and m are the same as before.
  • the silicone material can be provided by a single material.
  • examples of such materials are copolymers having siloxane macromers grafted thereto, which meet the functional limitations as defined above. That is, the non- silicone backbone of such polymers should have a molecular weight of from about 5,000 to about 1,000,000, and the polymer should have a glass transition temperature (Tg), i.e., the temperature at which the polymer changes from a brittle vitreous state to a plastic state, of greater than about -20°C. This material is not preferred when the carrier is more than about 95% water.
  • Tg glass transition temperature
  • the silicones used in the present invention typically have a viscosity of from about 1,000 (cst) to about 2,000,000 (cst), preferably from about 1,000 (cst) to about 1,500,000 (cst), more preferably from about 1,000 (cst) to about 1,000,000 (cst).
  • silicone When silicone is present, it is present at least an effective amount to provide lubrication of the fibers, typically from about 0.1% to about 4.5%, preferably from about 0.2% to about 4.0%, more preferably from about 0.3% to about 3 0%, by weight of the composition. Silicones present at levels higher than about 4.5%, by weight of the composition are not preferred because they can cause oil spots to appear on the fabric.
  • the present invention uses film-forming polymer to impart shape retention to fabric, particularly clothing. Any type of film-forming polymer can be used to impart shape retention however, some film-forming polymers are more preferred
  • the film-forming polymers useful in the present invention are comprised of monomers
  • Some nonlimitmg examples of monomers which can be used to form the film-forming polymers of the present invention include adipic acid, ethenyl formamide, diethylene triamine, vinyl amine, acrylic acid, methacrylic acid, N,N- dimethylacrylamide, N-t-butyl acrylamide, maleic acid, maleic anhydride, and its half esters, crotonic acid, itaconic acid, acrylamide, acrylate alcohols, hydroxyethyl methacrylate, vinyl pyrrolidone, vinyl ethers (such as methyl vinyl ether), maleimides, vinyl pyridine, vinyl imidazole and other polar vinyl heterocyclics, styrene sulfonate, ally
  • said film-forming polymer is soluble and/or dispersible in water and/or alcohol
  • Said film-forming polymer preferably has a molecular weight of at least about 500, more preferably from about 1,000 to about 2,000,000, most preferably from about 5,000 to about 1,000,000
  • homopolymers and copolymers which can be used as the film-forming polymers of the present invention are adipic acid / dimethylaminohydroxypropyl diethylenetriamine copolymer, adipic acid / epoxypropyl diethylenetriamine copolymer, poly(vinylpyrrolidone/dimethylaminoethyl methacrylate), polyvinyl alcohol, polyvinylpyridine n-oxide, methacryloyl ethyl betaine / methacrylates copolymer.
  • ethyl acrylate / methyl methacrylate / methacrylic acid / acrylic acid copolymer polyamine resins; and polyquatemary amine resins; poly(ethenylformamide); poly(vinylamine) hydrochloride; poly(vinyl alcohol-co-6% vinylamine); poly(vinyl alcohol-co-12% vinylamine), poly(vinyl alcohol-co-6% vinylamine hydrochloride); and poly( vinyl alcohol-co-12% vinylamine hydrochloride).
  • said copolymer and/or homopolymers are selected from the group consisting of adipic acid / dimethylaminohydroxypropyl diethylenetriamine copolymer; poly(vinylpyrrolidone/dimethylaminoethyl methacrylate); polyvinyl alcohol; ethyl acrylate / methyl methacrylate / methacrylic acid / acrylic acid copolymer; methacryloyl ethyl betaine / methacrylates copolymer; polyquatemary amine resins; poly(ethenylformamide); poly(vinylamine) hydrochloride; poly(vinyl alcohol-co-6% vinylamine); poly( vinyl alcohol-co-12% vinylamine); poly( vinyl alcohol-co-6% vinylamine hydrochloride); and poly(vinyl alcohol-co-12% vinylamine hydrochloride).
  • adipic acid / dimethylaminohydroxypropyl diethylenetriamine copolymer poly(vinylpyrrol
  • the film-forming polymer of the present invention is present at least an effective amount to provide shape retention, typically from about 0.1% to about 4.5%, preferably from about 0.2% to about 3%, more preferably from about 0.3% to about 2%, by weight of the composition. Polymer levels higher than about 4.5%, by weight of the composition, are not preferred due to the fact that an undesirable stiffness in the fabric can occur at these higher levels.
  • the wrinkle reducing active of the present invention comprises a mixture of the silicone and the film-forming polymer which together produce specific filming characteristics on fabric.
  • the filming properties of the wrinkle reducing active on the fabric are measured using Dynamic Mechanical Analysis (DMA) with the Perkin Elmer DMA 7 in tangential fiber extension geometry. Differences found in the Loss Modulus measurement of composition on fabric correlates with the Durable Press Grades (AATCC Method #124), hereinafter "DP grades", for garment appearance after treatment with the compositions of the present invention.
  • DMA Dynamic Mechanical Analysis
  • AATCC Method #124 Durable Press Grades
  • the invention comprises using Dynamic Mechanical Analysis, as described hereinafter to identify acceptable active mixtures.
  • Dynamic Mechanical aAnalysis can be found in "Anelastic and Dielectric Effects in Polymeric Solids," N.G. McCrum, B E. Read, and G. Williams, incorporated herein by reference.
  • the Dynamic Mechanical Analysis method involves applying a fixed volume of liquid sample to a fabric swatch in a tangential fiber extension geometry and monitoring the change in the fabric's ability to dampen the applied stress over time as the sample dries on the surface DMA measures the Loss Modulus (energy loss) over time as the wet fabric dries The reported quantity is the Loss Modulus Difference (LMD), the value for the dry fabric minus the value for the wet fabric It is calculated as an average value over time for the wet and dry fabric portions of the run Larger values of LMD correlate to higher DP grades for garment appearance This procedure can be used to determine the operability of many compositions B Filming Characteristics (Loss Modulus Difference) The Loss Modulus Parameter represents viscous loss
  • compositions of the present invention are tested as follows A 5.3mm x 20mm swatch of 100% cotton broadcloth is mounted in extensional geometry in a Perkin Elmer DMA 7, available from Perkin Elmer Corp It is important to keep the swatch centered and square to the geometry. Typically from about 10 microliters to about 25 microliters, preferably from about 15 microliters to about 25 microliters, more preferably from about 20 microliters to about 25 microliters, in three equal aliquots, of a liquid sample of the composition is applied using a microliter pipette in a way so as not to overwet the swatch or cause liquid to run off of the fabric.
  • the sample it is preferable to apply the sample near the upper portion of the swatch and allow it to wick down the swatch Once the sample is applied, no longer than 2 minutes are allowed to elapse before the run begins.
  • the sample height is read instrumentally, the stress values for analysis are set, 500mN for static stress, 450mN for dynamic test, and 110% tension, the furnace is raised, the temperature is allowed to equilibrate, and the run is begun Typically, the analysis is run at a temperature of from about 20°C to about 30°C. After the run, the data is smoothed using the Standard Smooth Routine in Change Curvetype® software to calculate the average wet and dry fabric ranges, this software accompanies the Perkin Elmer DMA 7.
  • a table is made of data points in the Select Calc® software, accompanying the Perkin Elmer DMA 7, starting at time 0.0 minutes with 0.7 minute increments. The values corresponding to times 2.8 - 7.7 minutes are averaged for the wet region, and 25.9 - 29.4 are averaged for the dry region. LMD is the dry region minus the wet region. Times can vary somewhat with each instrument and calibration, therefore, time are typically averaged over 4 to 5 minutes in the wet region and 4 to 5 minutes in the dry region.
  • the wrinkle reducing active of the present invention should have a LMD of greater than about 3.3 x 10 Pascal, preferably from about 3.3 x 10 ⁇ Pascal to about 5.5 x 10 ⁇ Pascal, more preferably from about 4.0 x 10 ⁇ Pascal to about 5.5 x 10? Pascal, and even more preferably from about 4.7 x 10 ⁇ Pascal to about 5.5 x 10 Pascal in order to work effectively.
  • Wrinkle reducing actives which have a loss modulus difference within these ranges typically show smooth surfaced, web-like, and pliable filming characteristics while wrinkle reducing actives which have a LMD below this range typically exhibit films which are brittle and rough surfaced.
  • the composition of the present invention typically results in a DP grades on the fabric of from about 3.3 to about 4.8, preferably from about 3.5 to about 4.8, more preferably from about 3.8 to about 4.8.
  • the wrinkle reducing active is preferably selected from the combinations consisting of aminoethylaminopropyl dimethyl siloxane and adipic acid/dimethylaminohydroxypropyl diethylenetriamine copolymer; aminoethylaminopropyl dimethyl siloxane, hydroxy terminated dimethyl siloxane (Dimethiconol), and poly(vinylpyrrolidone/dimethylaminoethyl methacrylate); aminoethylaminopropyl dimethyl siloxane, hydroxy terminated dimethyl siloxane (Dimethiconol), and polyquatemary amine resin; hydroxy terminated dimethyl siloxane (Dimethiconol) and methacryloyl ethyl betaine /
  • said wrinkle reducing active is selected from the combinations consisting of polydimethylsiloxane and adipic acid/dimethylaminohydroxypropyl diethlenetriamine copolymer; and aminoethylaminopropyl dimethyl siloxane, hydroxy terminated dimethyl siloxane (Dimethiconol), and polyquatemary amine resin; even more preferably said wrinkle reducing active is selected from the combination consisting of hydroxy terminated dimethyl siloxane (Dimethiconol) and methacryloyl ethyl betaine / methacrylates copolymer; and polydimethylsiloxane and ethyl acrylate / methyl methacrylate / methacrylic acid / acrylic acid copolymer; and most preferably said wrinkle reducing active is selected from the combination consisting of aminoethylaminopropyl dimethyl siloxane and adipic acid/dimethylaminohydroxypropyl diethylenetriamine copoly
  • 10 1 to about 1: 10, preferably from about 5: 1 to about 1 :5, and more preferably from about 2: 1 to about 1 :2.
  • the preferred wrinkle reducing active is silicone plus film-forming polymer, present at a level of from about 0.1% to about 50%, preferably from about 0.5% to about 10%, more preferably from about 0.5% to about 2%, by weight of the composition.
  • Concentrated compositions can also be used in order to provide a less expensive product.
  • a concentrated product i.e., when the wrinkle reducing active is from about 5% to about 50%, by weight of the composition, it is preferable to dilute the composition before treating fabric.
  • the wrinkle reducing active is diluted with about 50% to about 10,000%, more preferably from about 50% to about 8,000%, and even more preferably from about 50% to about 5,000%, by weight of the composition, of water.
  • the composition of the present invention can optionally contain an ethoxylated surfactant.
  • an ethoxylated surfactant When an ethoxylated surfactant is added to the composition of the present invention it is typically added at a level of from about 0.05% to about 3%, preferably from about 0.05% to about 2%, and more preferably from about 0.1% to about 1%, by weight of the composition.
  • Said surfactant is preferably included when the composition is used in a spray dispenser in order to enhance the spray characteristics of the composition and allow the composition to distribute more evenly, and to prevent clogging of the spray apparatus.
  • the ethoxylated surfactant includes compounds having the general formula:
  • R- ⁇ is an alkyl aryl group or an alkyl group having from about 6 to about 18 carbon atoms, preferably from about 8 to about 14, more preferably from about 10 to about 14 carbon atoms; s is an integer from about 3 to about 45, preferably from about 3 to about 20, more preferably from about 5 to about 15; and B is a hydrogen, a carboxylate group , or a sulfate group.
  • said ethoxylated surfactant is selected from the group consisting of carboxylated alcohol ethoxylate, also known as ether carboxylate, having a hydrophobic group with from about 12 to about 16 carbon atoms and from about 5 to about 13 ethoxylate groups; alcohol ethoxylate or secondary alcohol ethoxylate having from about 8 to about 20 carbon atoms and from about 4 to about 50 ethoxylate groups; and alkyl phenyl ethoxylate or alkyl aryl ethoxylate having from about 8 to about 10 carbon atoms, preferably from about 14 to 18 carbon atoms and from about 4 to about 50 ethoxylate groups.
  • carboxylated alcohol ethoxylate also known as ether carboxylate, having a hydrophobic group with from about 12 to about 16 carbon atoms and from about 5 to about 13 ethoxylate groups
  • alcohol ethoxylate or secondary alcohol ethoxylate having from about 8 to about 20 carbon atoms and from about 4
  • Another ethoxylated surfactant suitable for use in the present invention has the formula.
  • PE represents -CH 2 CH 2 CH O(EO) g (PO) Z;
  • PO represents 1,2-propyleneoxy
  • ethoxylated surfactants suitable for use in the present invention include ethoxylated quaternary ammonium surfactants.
  • Some preferred ethoxylated quatemary ammonium surfactants include PEG-5 cocomonium methosulfate, PEG- 15 cocomonium chloride; PEG- 15 oleammonium chloride, and bis(polyethoxyethanol)tallow ammonium chloride. 2 Soil Release Polymers In the present invention, an optional soil release agent can be added.
  • the wrinkle reducing composition of the present invention herein can contain from about 0% to about 5%, preferably from about 0.05% to about 3%, more preferably from about 0.1% to about 2%, by weight of the composition, of soil release agent.
  • Polymeric soil release agents useful in the present invention include copolymeric blocks of terephthalate and polethylene oxide or polypropylene oxide, and the like
  • a preferred soil release agent is a copolymer having blocks of terephthalate and polyethylene oxide. More specifically, these polymers are comprised of repeating units of ethylene terephthalate and polyethylene oxide terephthalate at a molar ratio of ethylene terephthalate units to polyethylene oxide terephthalate units of from about 25:75 to about 35:65, said polyethylene oxide terephthalate containing polyethylene oxide blocks having molecular weights of from about 300 to about 2000. The molecular weight of this polymeric soil release agent is in the range of from about 5,000 to about 55,000.
  • Another preferred polymeric soil release agent is a crystallizable polyester with repeat units of ethylene terephthalate units containing from about 10% to about 15% by weight of ethylene terephthalate units together with from about 10% to about 50% by weight of polyoxyethylene terephthalate units, derived from a polyoxyethylene glycol of average molecular weight of from about 300 to about 6,000, and the molar ratio of ethylene terephthalate units to polyoxyethylene terephthalate units in the crystallizable polymeric compound is between 2.1 and 6: 1
  • this polymer include the commercially available materials Zelcon 4780® (from Dupont) and Milease T® (from ICI).
  • Highly preferred soil release agents are polymers of the generic formula:
  • each X can be a suitable capping group, with each X typically being selected from the group consisting of H, and alkyl or acyl groups containing from about 1 to about 4 carbon atoms, each t is selected for water solubility and generally is from about 6 to about 1 13, preferably from about 20 to about 50.
  • u is critical to formulation in a liquid composition having a relatively high ionic strength There should be very little material in which u is greater than 10. Furthermore, there should be at least 20%, preferably at least 40%, of material in which u ranges from about 3 to about 5.
  • the R" moieties are essentially 1,4-phenylene moieties.
  • the term "the R" moieties are essentially 1,4-phenylene moieties” refers to compounds where the R" moieties consist entirely of 1,4-phenylene moieties, or are partially substituted with other arylene or alkarylene moieties, alkylene moieties, alkenylene moieties, or mixtures thereof.
  • aArylene and alkarylene moieties which can be partially substituted for 1,4-phenylene include 1,3-phenylene, 1 ,2-phenylene, 1,8-naphthylene, 1,4-naphthylene, 2,2-biphenylene, 4,4-biphenylene, and mixtures thereof.
  • aAlkylene and alkenylene moieties which can be partially substituted include 1,2-propylene, 1,4- butylene, 1,5-pentylene, 1,6-hexamethylene, 1,7-heptamethylene, 1,8-octamethylene, 1,4-cyclohexylene, and mixtures thereof.
  • the degree of partial substitution with moieties other than 1,4-phenylene should be such that the soil release properties of the compound are not adversely affected to any great extent.
  • the degree of partial substitution which can be tolerated will depend upon the backbone length of the compound, i.e., longer backbones can have greater partial substitution for 1,4- phylene moieties.
  • compounds where the R" comprise from about 50% to about 100% 1,4-phenylene moieties (from 0% to about 50% moieties other than 1,4- phenylene) have adequate soil release activity.
  • polyesters made according to the present invention with a 40:60 mole ratio of isophthalic (1,3- phenylene) to terephthalic (1,4-phenylene) acid have adequate soil release activity.
  • the R 6 moieties consist entirely of (i.e., comprise 100%) 1,4-phenylene moieties, i.e., each R" moiety is 1,4-phenylene.
  • suitable ethylene or substituted ethylene moieties include ethylene, 1,2-propylene, 1,2-butylene, 1 ,2-hexylene, 3-methoxy-l,2-propylene, and mixtures thereof.
  • the R' moieties are essentially ethylene moieties, 1,2- propylene moieties, or mixtures thereof. Inclusion of a greater percentage of ethylene moieties tends to improve the soil release activity of compounds. Surprisingly, inclusion of a greater percentage of 1,2-propylene moieties tends to improve the water solubility of compounds.
  • 1,2-propylene moieties or a similar branched equivalent is desirable for incorporation of any substantial part of the soil release component in the liquid fabric softener compositions.
  • composition of the present invention can optionally include antistatic agents.
  • antistatic agents When said antistatic agents are present in the composition they are present at a level of from about 0% to about 5%, preferably from about 0.005% to about 5%, more preferably from about 0.05% to about 2%, and most preferably from about 0.2% to about 1%, by weight of the composition.
  • Preferred antistatic agents of the present invention are cationic surfactants, preferably quatemary ammonium salts having the general formulas: or
  • R*-* group is a C]o-C 2 hydrocarbon group, preferably a C ⁇ 2 -C]g alkyl group or the corresponding ester linkage interrupted group with a short alkylene (C1-C4) group between the ester linkage and the N, and having a similar terminal hydrocarbon group, g., a fatty acid ester of choline, preferably Cj 2 -Ci4 (coco) choline ester and/or Cjg-Cjg tallow choline ester.
  • Each R ⁇ is a C 1-C4 alkyl or substituted (e.g., hydroxy) alkyl, or hydrogen, preferably methyl; each R ⁇ is a benzyl group; and the counterion X" is a softener compatible anion, for example, chloride, bromide, methyl sulfate, etc.
  • Some preferred quaternary ammonium compounds include alkyl benzyl dimethyl ammonium chloride; dicoco quatemary ammonium chloride; coco dimethyl benzyl ammonium chloride; soya trimethyl quatemary ammonium chloride; hydrogenated tallow dimethyl benzyl ammonium chloride; and methyl dihydrogenated tallow benzyl ammonium chloride.
  • Other preferred antistatic agents of the present invention are alkyl imidazolinium salts having the general formula:
  • Y 2 is -C(O)-O-, -O-(O)-C-, -C(O)-N(R* 4 ), or -N(R )-C(O)- in which R 14 is hydrogen or a C1-C4 alkyl radical; R ⁇ and R ⁇ are each independently selected from R8 and R ⁇ as defined hereinbefore for the cationic surfactant, with only one being R 8 ; and each R ⁇ 2 is a C J-C4 alkyl radical.
  • Suitable antistatic agents are the ion pairs of, e.g., anionic detergent surfactants and fatty amines, or quatemary ammonium derivatives thereof, e.g., those disclosed in U.S. Pat. No. 4,756,850, Nayar, issued July 12, 1988, said patent being incorporated herein by reference.
  • the ion pair complexes can be represented by the following formula:
  • each R ⁇ 4 can independently be C ⁇ 2 -C 2 o alkyl or alkenyl, and R ⁇ is H or CH3.
  • A" represents an anionic compound and includes a variety of anionic surfactants, as well as related shorter alkyl chain compounds which need not exhibit surface activity.
  • a * is selected from the group consisting of alkyl sulfonates, aryl sulfonates, alkylaryl sulfonates, alkyl sulfates, dialkyl sulfosuccinates, alkyl oxybenzene sulfonates, acyl isethionates, acylalkyl taurates, alkyl ethoxylates sulfates, olefin sulfates, preferably benzene sulfonates, and C1-C5 linear alkyl benzene sulfonates, or mixtures thereof.
  • Suitable antistatic agents are ethoxylated and/or propylated sugar derivatives.
  • Said sugar derivatives have an empirical formula as follows:
  • Rl6 z ( SU gar)(Rl 7 O) w C
  • R ⁇ is a hydrophobic group containing from about 8 to about 30, preferably from about 12 to about 22, more preferably from about 16 to about 18 carbon atoms
  • "sugar” refers to a polyhydroxy group, preferably derived from sugar, sugar alcohol, or similar polyhydroxy compound
  • R 17 is an alkylene group, preferably ethylene or propylene, more preferably ethylene
  • z is a number from 1 to about 4, preferably 2
  • w is a number from about 5 to about 100, preferably from about 10 to about 40.
  • a preferred compound of this type is polyethoxylated sorbitan monostearate, e.g., Glycosperse S-20® from Lonza, which contains about 20 ethoxylate moieties per molecule.
  • the present invention can include optional components conventionally used in textile treatment compositions, for example, colorants, perfumes, preservatives, bactericides, optical brighteners, opacifiers, surfactants, anti-shrinkage agents, germicides, fungicides, anti-oxidants, and the like.
  • the compositions are preferably free of any material that would soil or stain fabric, and are also substantially free of starch. Typically, there should be less than about 0.5%, by weight of the composition, preferably less than about 0.3%, more preferably less than about 0.1%, by weight of the composition, of starch and/or modified starch.
  • the liquid carrier used in the composition of the present invention is preferably an aqueous system comprising water.
  • the carrier can contain a low molecular weight organic solvent that is highly soluble in water, e.g., C1-C4 monohydric alcohols, C 2 -C ⁇ polyhydric alcohols, such as alkylene glycols, polyalkylene glycols, etc., alkylene carbonates, and mixtures thereof.
  • these water-soluble solvents include ethanol, propanol, isopropanol, etc.
  • Water is a preferred liquid carrier due to its low cost, availability, safety, and environmental compatibility. Water can be distilled, deionized, or tap water.
  • the level of liquid carrier in the compositions of the present invention is typically greater than about 80%, preferably greater than about 90%, more preferably greater than about 95%, by weight of the composition.
  • the level of liquid carrier is typically from about 50% to about 95%, by weight of the composition, preferably from about 60% to about 93%, more preferably from about 60% to about 85%, by weight of the composition.
  • an article of manufacture comprising an article of manufacture comprising a wrinkle reducing composition comprising a wrinkle reducing active selected from the group consisting of an effective amount of silicone, an effective amount of film-forming polymer and mixtures thereof, and a liquid carrier, and a spray dispensing device.
  • the dilute compositions i.e., compositions containing from about 0.1% to about 5%, by weight of the composition, of wrinkle reducing active, of the present invention are preferably sprayed onto fabrics and therefore are typically packaged in a spray dispenser.
  • the spray dispenser can be any of the manually activated means for producing a spray of liquid droplets as is known in the art, e.g.
  • trigger-type, purrip- type, non-aerosol self-pressurized, and aerosol-type spray means It is preferred that at least about 70%, more preferably, at least about 80%, most preferably at least about 90% of the droplets have a particle size of smaller than about 200 microns.
  • the spray dispenser can be an aerosol dispenser.
  • Said aerosol dispenser comprises a container which can be constructed of any of the conventional materials employed in fabricating aerosol containers.
  • the dispenser must be capable of withstanding internal pressure in the range of from about 20 to about 110 p.s.i.g., more preferably from about 20 to about 70 p.s.i.g.
  • the one important requirement concerning the dispenser is that it be provided with a valve member which will permit the wrinkle reducing composition contained in the dispenser to be dispensed in the form of a spray of very fine, or finely divided, particles or droplets.
  • the aerosol dispenser utilizes a pressurized sealed container from which the wrinkle reducing composition is dispensed through a special actuator/valve assembly under pressure.
  • the aerosol dispenser is pressurized by incorporating therein a gaseous component generally known as a propellant.
  • a gaseous component generally known as a propellant.
  • a propellant e.g., gaseous hydrocarbons such as isobutane, and mixed halogenated hydrocarbons, are not preferred.
  • Halogenated hydrocarbon propellants such as chlorofluoro hydrocarbons have been alleged to contribute to environmental problems.
  • Preferred propellants are compressed air, nitrogen, inert gases, carbon dioxide, etc.
  • the spray dispenser can be a self-pressurized non-aerosol container having a convoluted liner and an elastomeric sleeve.
  • Said self-pressurized dispenser comprises a liner/sleeve assembly containing a thin, flexible radially expandable convoluted plastic liner of from about 0.010 to about 0.020 inch thick, inside an essentially cylindrical elastomeric sleeve.
  • the liner/sleeve is capable of holding a substantial quantity of odor-absorbing fluid product and of causing said product to be dispensed.
  • aAnother type of aerosol spray dispenser is one wherein a barrier separates the wrinkle reducing composition from the propellant (preferably compressed air or nitrogen), as is disclosed in U.S. Pat. No. 4,260, 1 10, issued April 7, 1981, incorporated herein by reference.
  • a dispenser is available from EP Spray Systems, East Hanover, New Jersey. More preferably, the spray dispenser is a non-aerosol, manually activated, pump-spray dispenser.
  • Said pump-spray dispenser comprises a container and a pump mechanism which securely screws or snaps onto the container.
  • the container comprises a vessel for containing the wrinkle reducing composition to be dispensed.
  • the pump mechanism comprises a pump chamber of substantially fixed volume, having an opening at the inner end thereof. Within the pump chamber is located a pump stem having a piston on the end thereof disposed for reciprocal motion in the pump chamber.
  • the pump stem has a passageway there through with a dispensing outlet at the outer end of the passageway and an axial inlet port located inwardly thereof.
  • the container and the pump mechanism can be constructed of any conventional material employed in fabricating pump-spray dispensers, including, but not limited to: polyethylene; polypropylene; polyethyleneterephthalate; blends of polyethylene, vinyl acetate, and rubber elastomer. Other materials can include stainless steel.
  • the spray dispenser is a manually activated trigger-spray dispenser.
  • Said trigger-spray dispenser comprises a container and a trigger both of which can be constructed of any of the conventional material employed in fabricating trigger-spray dispensers, including, but not limited to: polyethylene; polypropylene; polyacetal; polycarbonate; polyethyleneterephthalate; polyvinyl chloride; polystyrene; blends of polyethylene, vinyl acetate, and rubber elastomer. Other materials can include stainless steel and glass.
  • the trigger-spray dispenser does not incorporate a propellant gas.
  • the trigger-spray dispenser herein is typically one which acts upon a discrete amount of the wrinkle reducing composition itself, typically by means of a piston or a collapsing bellows that displaces the composition through a nozzle to create a spray of thin liquid.
  • Said trigger-spray dispenser typically comprises a pump chamber having either a piston or bellows which is movable through a limited stroke response to the trigger for varying the volume of said pump chamber. This pump chamber or bellows chamber collects and holds the product for dispensing.
  • the trigger spray dispenser typically has an outlet check valve for blocking communication and flow of fluid through the nozzle and is responsive to the pressure inside the chamber.
  • the trigger As the trigger is compressed, it acts on the fluid in the chamber and the spring, increasing the pressure on the fluid.
  • the bellows spray dispenser As the bellows is compressed, the pressure increases on the fluid. The increase in fluid pressure in either trigger spray dispenser acts to open the top outlet check valve. The top valve allows the product to be forced through the swirl chamber and out the nozzle to form a discharge pattern. .An adjustable nozzle cap can be used to vary the pattern of the fluid dispensed.
  • the spring acts on the piston to return it to its original position.
  • the bellows spray dispenser the bellows acts as the spring to return to its original position. This action causes a vacuum in the chamber.
  • the preferred trigger sprayers are the blue inserted Guala® sprayer, available from Berry Plastics Corp., the Calmar TS800-1A® sprayers, available from Calmar Inc., or the CSI T7500® available from Continental Sprayers, Inc., because of the fine uniform spray characteristics, spray volume, and pattern size.
  • Any suitable bottle or container can be used with the trigger sprayer, the preferred bottle is a 17 fl-oz.
  • bottle (about 500 ml) of good ergonomics similar in shape to the Cinch® bottle. It can be made of any materials such as high density polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyethylene terephthalate, glass, or any other material that forms bottles. Preferably, it is made of high density polyethylene or polyethylene terephthalate.
  • a finger pump can be used with canister or cylindrical bottle. The preferred pump for this application is the cylindrical Euromist II® from Seaquest Dispensing. All percentages, ratios, and parts herein, in the Specification, Examples, and Claims, are by weight and are approximations unless otherwise stated.
  • An effective amount of the composition of the present invention is preferably sprayed onto fabrics, particularly clothing.
  • an effective amount should be deposited onto the fabric without causing saturation of the fabric, typically from about 10% to about 85%, preferably from about 15% to about 65%, more preferably from about 20% to about 50%, by weight of the fabric.
  • the amount of active typically sprayed onto the fabric is from about 0.1% to about 4%, preferably from about 0.2% to about 3%, more preferably from about 0.3% to about 2%, by weight of the fabric.
  • the fabric is optionally, but preferably stretched.
  • the fabric is typically stretched perpendicular to the wrinkle
  • the fabric can also be smoothed by hand after it has been sprayed. The smoothing movement works particularly well on areas of clothing that have interface sewn into them, or on the hem of clothing. Once the fabric has been sprayed and optionally, but preferably, stretched, it is hung until dry.
  • composition of the present invention can also be used as an ironing aid.
  • An effective amount of the composition can be sprayed onto fabric, wherein said fabric should not be sprayed to saturation.
  • the fabric can be ironed at the normal temperature at which it should be ironed.
  • the fabric can be sprayed with an effective amount of the composition, allowed to dry and then ironed, or sprayed and ironed immediately.
  • Sandopan DTC 9 ® 90 0.30 0.10 0.10 0.10 0.10 0.10
  • Preservative 1.5 0.0003 0.0003 0.0003 0.0003 0.0003 0.0003
  • Cartaretin F-23® 23 0.46 0.46 Copolymer 937® I 3 20 0.65 Vinex 2019®1 4 12.5 0.50
  • Diaformer Z-SM® 30 0.80 Silwet l.76071 5 100 0.10
  • Neodol 23-6.5®1 6 100 ... 0.20 0.10 0.10
  • Sandopan DTC® 90 0.30 ... ... 0.10 Perfume 100 0.015 0.015 0.015 0.015 0.01
  • Preservative 1.5 0.0003 0.0003 0.0003 0.0003 0.0003 0.0003
  • the ethoxylated surfactant is added to the deiomzed water at about 21 °C to about 27°C with stirring
  • the film-forming polymer is added to the water/surfactant mixture and stirring is continued
  • the silicone is added to the mixture with a low amount of agitation to form a homogenous mixture
  • the perfume and antimicrobial are added The mixture is stirred for about 3 to about 5 minutes with low agitation
  • Copolymer 958® 50 cakes 05 _. .- 05 ._
  • the compositions are prepared as in Example I.
  • the Loss Modulus Difference is determined by applying fixed volume of liquid sample to a fabric swatch, i.e. 100% cotton broadcloth, in a tangential fiber extension geometry and monitoring the change in the fabric's ability to dampen the applied stress over time as the sample dries on the surface. Measurements are made isothermally at from about 20°C to about 30°C, e.g., room temperature. Loss Modulus, or energy loss, is measured as the fabric dries and is reported as the Loss Modulus Difference (LMD) between the dry fabric at the end of the run and the wet fabric at the beginning of the run.
  • LMD Loss Modulus Difference
  • compositions are placed in a CSI T7500® sprayer and the sprayer is used to treat wrinkled fabrics.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
PCT/US1995/014030 1994-11-10 1995-10-31 Wrinkle reducing composition WO1996015309A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP8516102A JPH10508911A (ja) 1994-11-10 1995-10-31 しわを減少させる組成物
MX9703522A MX9703522A (es) 1994-11-10 1995-10-31 Composicion para reducir arrugas.
BR9509712A BR9509712A (pt) 1994-11-10 1995-10-31 Composição de redeção de pregas
CA002205025A CA2205025C (en) 1994-11-10 1995-10-31 Wrinkle reducing composition
EP95939646A EP0791097A2 (en) 1994-11-10 1995-10-31 Wrinkle reducing composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US33831394A 1994-11-10 1994-11-10
US08/338,313 1994-11-10

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WO1996015309A3 WO1996015309A3 (en) 1996-07-18

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BR (1) BR9509712A (pt)
CA (1) CA2205025C (pt)
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WO (1) WO1996015309A2 (pt)
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US5695677A (en) * 1995-07-03 1997-12-09 R & C Products Pty Limited Ironing aid
WO1998056888A1 (en) * 1997-06-09 1998-12-17 The Procter & Gamble Company Uncomplexed cyclodextrin compositions for odor control
WO1998056890A1 (en) * 1997-06-09 1998-12-17 The Procter & Gamble Company Uncomplexed cyclodextrin compositions for odor and wrinkle control
WO1999055813A1 (en) * 1998-04-27 1999-11-04 The Procter & Gamble Company Improved uncomplexed cyclodextrin compositions for odor control
WO1999055814A1 (en) * 1998-04-27 1999-11-04 The Procter & Gamble Company Improved uncomplexed cyclodextrin compositions for odor and wrinkle control
WO1999055815A1 (en) * 1998-04-27 1999-11-04 The Procter & Gamble Company Improved uncomplexed cyclodextrin compositions for odor control
WO2000008249A1 (en) * 1998-08-04 2000-02-17 The Procter & Gamble Company Wrinkle reducing composition
US6251850B1 (en) 1999-05-21 2001-06-26 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Fabric softening compositions containing emulsified silicone
US6255271B1 (en) 1998-09-16 2001-07-03 Unilever Home & Personal Care, Usa, Division Of Conopco Fabric care composition
EP1201816A1 (en) * 2000-10-27 2002-05-02 The Procter & Gamble Company Clothes treatment for dry wrinkle resistance
EP1201817A1 (en) * 2000-10-27 2002-05-02 The Procter & Gamble Company Clothes treatment for dry wrinkle resistance
WO2002092745A1 (en) * 2001-05-15 2002-11-21 Unilever Plc Detergent composition
US6491840B1 (en) * 2000-02-14 2002-12-10 The Procter & Gamble Company Polymer compositions having specified PH for improved dispensing and improved stability of wrinkle reducing compositions and methods of use
US6495058B1 (en) 2000-02-14 2002-12-17 The Procter & Gamble Company Aqueous wrinkle control compositions dispensed using optimal spray patterns
US6528013B1 (en) 1998-04-27 2003-03-04 The Procter & Gamble Company Uncomplexed cyclodextrin compositions for odor and wrinkle control
US6596034B1 (en) 1999-11-25 2003-07-22 Unilever Home And Personal Care Usa Division Of Conopco, Inc. Textile material
WO2003083029A1 (en) * 2002-04-03 2003-10-09 Unilever Plc Fabric care composition
US6746617B2 (en) * 2001-09-10 2004-06-08 Procter & Gamble Company Fabric treatment composition and method
WO2004061197A1 (ja) * 2002-12-27 2004-07-22 Lion Corporation 液体柔軟剤組成物
US7008916B2 (en) 2002-04-03 2006-03-07 Unilever Home & Personal Care Usa Fabric care composition
US7670388B2 (en) 2005-10-14 2010-03-02 Kao Corporation Fiber-treating composition
US7981854B2 (en) 2006-03-07 2011-07-19 Kao Corporation Wrinkle-removing composition comprising a propoxylated/ethoxylated alkyl surfactant
WO2019110960A1 (en) * 2017-12-04 2019-06-13 Novolab Limited Improvements relating to crease recovery in textiles
CN112176726A (zh) * 2020-10-11 2021-01-05 浙江梦森服饰有限公司 一种具有防皱功能的强触感羊毛面料的制备方法
WO2023099593A1 (en) * 2021-12-02 2023-06-08 Unilever Ip Holdings B.V. Fabric conditioner

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US6910579B2 (en) 2002-05-28 2005-06-28 Georgia-Pacific Corporation Refillable flexible sheet dispenser
EP1788147B1 (en) 2004-09-07 2011-03-16 Kao Corporation Crease removing composition
KR101261256B1 (ko) 2005-05-23 2013-05-07 다우 코닝 코포레이션 사카라이드-실록산 공중합체를 포함하는 퍼스널 케어조성물
EP2609138B1 (en) 2010-08-23 2017-05-17 Dow Corning Corporation Saccharide siloxanes stable in aqueous environments and methods for the preparation and use of such saccharide siloxanes

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EP0292909A2 (en) * 1987-05-26 1988-11-30 Colgate-Palmolive Company Composition and method for removal of wrinkles in fabrics

Cited By (39)

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US5695677A (en) * 1995-07-03 1997-12-09 R & C Products Pty Limited Ironing aid
EP0836657A1 (en) * 1995-07-03 1998-04-22 R & C PRODUCTS PTY. LIMITED Ironing aid
EP0836657A4 (en) * 1995-07-03 1999-11-24 R & C Products Pty Ltd IRONING AID
WO1998056888A1 (en) * 1997-06-09 1998-12-17 The Procter & Gamble Company Uncomplexed cyclodextrin compositions for odor control
WO1998056890A1 (en) * 1997-06-09 1998-12-17 The Procter & Gamble Company Uncomplexed cyclodextrin compositions for odor and wrinkle control
WO1999055815A1 (en) * 1998-04-27 1999-11-04 The Procter & Gamble Company Improved uncomplexed cyclodextrin compositions for odor control
WO1999055814A1 (en) * 1998-04-27 1999-11-04 The Procter & Gamble Company Improved uncomplexed cyclodextrin compositions for odor and wrinkle control
WO1999055813A1 (en) * 1998-04-27 1999-11-04 The Procter & Gamble Company Improved uncomplexed cyclodextrin compositions for odor control
US6528013B1 (en) 1998-04-27 2003-03-04 The Procter & Gamble Company Uncomplexed cyclodextrin compositions for odor and wrinkle control
WO2000008249A1 (en) * 1998-08-04 2000-02-17 The Procter & Gamble Company Wrinkle reducing composition
US6255271B1 (en) 1998-09-16 2001-07-03 Unilever Home & Personal Care, Usa, Division Of Conopco Fabric care composition
US6277810B2 (en) 1998-09-16 2001-08-21 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Dryer-added fabric care compositions containing amide-epichlorohydrin resins
US6251850B1 (en) 1999-05-21 2001-06-26 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Fabric softening compositions containing emulsified silicone
US6596034B1 (en) 1999-11-25 2003-07-22 Unilever Home And Personal Care Usa Division Of Conopco, Inc. Textile material
US6491840B1 (en) * 2000-02-14 2002-12-10 The Procter & Gamble Company Polymer compositions having specified PH for improved dispensing and improved stability of wrinkle reducing compositions and methods of use
US6495058B1 (en) 2000-02-14 2002-12-17 The Procter & Gamble Company Aqueous wrinkle control compositions dispensed using optimal spray patterns
US6652766B1 (en) 2000-02-14 2003-11-25 The Procter & Gamble Company Articles to aid the ironing of fabrics and methods of use
US6645392B2 (en) 2000-02-14 2003-11-11 The Procter & Gamble Company Method of removing wrinkles from fabric
WO2002070815A2 (en) * 2000-10-27 2002-09-12 The Procter & Gamble Company Clothes treatment for dry wrinkle resistance
WO2002070815A3 (en) * 2000-10-27 2002-10-31 Procter & Gamble Clothes treatment for dry wrinkle resistance
WO2002068751A3 (en) * 2000-10-27 2003-01-16 Procter & Gamble Clothes treatment for dry wrinkle resistance
EP1201817A1 (en) * 2000-10-27 2002-05-02 The Procter & Gamble Company Clothes treatment for dry wrinkle resistance
EP1201816A1 (en) * 2000-10-27 2002-05-02 The Procter & Gamble Company Clothes treatment for dry wrinkle resistance
US6984336B2 (en) 2000-10-27 2006-01-10 The Procter & Gamble Company Clothes treatment for dry wrinkle resistance
US7049276B2 (en) 2000-10-27 2006-05-23 The Procter & Gamble Company Clothes treatment for dry wrinkle resistance utilizing an aminosilicone containing a sterically hindered functional group
WO2002068751A2 (en) * 2000-10-27 2002-09-06 The Procter & Gamble Company Clothes treatment for dry wrinkle resistance
WO2002092745A1 (en) * 2001-05-15 2002-11-21 Unilever Plc Detergent composition
US6767371B2 (en) 2001-05-15 2004-07-27 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Detergent composition
US6746617B2 (en) * 2001-09-10 2004-06-08 Procter & Gamble Company Fabric treatment composition and method
WO2003083029A1 (en) * 2002-04-03 2003-10-09 Unilever Plc Fabric care composition
US7008916B2 (en) 2002-04-03 2006-03-07 Unilever Home & Personal Care Usa Fabric care composition
US7030076B2 (en) 2002-04-03 2006-04-18 Unilever Home & Personal Care Usa A Division Of Conopco, Inc. Fabric care composition comprising a block copolymer having a methoxyethyl acrylate core polymer and an alkyl methacrylate flanking polymer
WO2004061197A1 (ja) * 2002-12-27 2004-07-22 Lion Corporation 液体柔軟剤組成物
US7670388B2 (en) 2005-10-14 2010-03-02 Kao Corporation Fiber-treating composition
US7981854B2 (en) 2006-03-07 2011-07-19 Kao Corporation Wrinkle-removing composition comprising a propoxylated/ethoxylated alkyl surfactant
WO2019110960A1 (en) * 2017-12-04 2019-06-13 Novolab Limited Improvements relating to crease recovery in textiles
CN112176726A (zh) * 2020-10-11 2021-01-05 浙江梦森服饰有限公司 一种具有防皱功能的强触感羊毛面料的制备方法
CN112176726B (zh) * 2020-10-11 2023-02-10 浙江梦森服饰有限公司 一种具有防皱功能的羊毛面料的制备方法
WO2023099593A1 (en) * 2021-12-02 2023-06-08 Unilever Ip Holdings B.V. Fabric conditioner

Also Published As

Publication number Publication date
JPH10508911A (ja) 1998-09-02
EP0791097A2 (en) 1997-08-27
CA2205025C (en) 2001-08-21
MX9703522A (es) 1997-08-30
BR9509712A (pt) 1998-06-16
CA2205025A1 (en) 1996-05-23
WO1996015309A3 (en) 1996-07-18
ZA959557B (en) 1996-05-28

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