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WO2000008127A1 - Composition conferant une resistance au froissement - Google Patents

Composition conferant une resistance au froissement Download PDF

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Publication number
WO2000008127A1
WO2000008127A1 PCT/US1999/017554 US9917554W WO0008127A1 WO 2000008127 A1 WO2000008127 A1 WO 2000008127A1 US 9917554 W US9917554 W US 9917554W WO 0008127 A1 WO0008127 A1 WO 0008127A1
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WO
WIPO (PCT)
Prior art keywords
composition
cross
resin
epichlorohydrin
linking
Prior art date
Application number
PCT/US1999/017554
Other languages
English (en)
Inventor
Markus Altmann
An Bernaerts
Els Goossens
Bruno Albert Jean Hubesch
Axel Masschelein
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.)
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Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8237079&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2000008127(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to BR9912708-3A priority Critical patent/BR9912708A/pt
Priority to CA002338791A priority patent/CA2338791A1/fr
Priority to JP2000563754A priority patent/JP2002522650A/ja
Priority to US09/762,080 priority patent/US6514932B1/en
Priority to AU53328/99A priority patent/AU5332899A/en
Publication of WO2000008127A1 publication Critical patent/WO2000008127A1/fr

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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
    • C11D3/0005—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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • 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
    • C11D3/0021—Dye-stain or dye-transfer inhibiting compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • 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
    • C11D3/3723—Polyamines or polyalkyleneimines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • D06M15/11—Starch or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
    • D06M15/3562—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53—Polyethers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/55—Epoxy resins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/59—Polyamides; Polyimides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61—Polyamines polyimines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease

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, wrinkle resistance.
  • solutions obtained from industry are not usually transposable to domestic treatments. Indeed, in industrial processes a strict control over parameters such as pH, electrolyte concentration, water hardness, temperature, etc.. is possible whereas in a domestic washing machine, such a high level of control is not possible. Moreover, it has been found that solutions from industry do not effectively bind the cellulosic fibers in domestic rinse application.
  • domestic durable press treatments require conditions that industrial treatment do not have to fulfill.
  • the compounds or compositions thereof need to manifest at least one of the following properties:
  • aldehyde based cross-linker technologies are less favoured in domestic process from an environmental and safety standpoint because contrary to industry where the process is controlled, in domestic process the consumer is the only person using the product, thus enabling the possibility of misuse. Further, high levels of aldehyde tends to produce an odour which would deter the consumer from using it again. Thus, it is desired to provide durable processes for use in domestic process which are safe to the consumer and provide a good odour acceptance.
  • the present invention is a composition comprising: i)-a fabric softening compound; and ii)- a cross-linking resin having the property of being cationic.
  • the present invention relates to a method of treating fabric which comprises the steps of: i)-contacting the fabrics with an epichlorohydrin adducts of polyamine resins, polyethyleneimine resins, cationic starch, polydiallyldimethylammonium chloride, and mixtures thereof, and ii)- curing the composition.
  • the present invention relates to a method of treating fabric which comprises the steps of: i)-contacting the fabrics with a resin compound or composition as defined herein, and ii)- curing the composition using a domestic process.
  • the present invention relates to compositions which provide effective durable press on treated fabrics, especially when treated in rinse application.
  • An essential component of the invention is a cross-linking resin having the property of being cationic.
  • cross-linking resin having the property of being cationic it is meant that the resin is at least partially positively charged. It is not however necessary that the reactive part of the molecule carries the positive charge.
  • polymeric resins can be based on positively charged monomers which help the deposition on the fibers. Since the cross-linking resins are cationic, i.e. positively charged, they are deposited and well retained on the negatively charged cellulosic fibers when these resins are added to the final rinse of a laundry process.
  • Cross-linking resins having the property of being cationic suitable for use herein are those commonly known as having wet strength in the paper field. At least two mechanisms have been postulated to account for the mechanism by which wet strength resin act. One is that wet strength resins form covalent bonds between adjacent fibers while another is that the wet strength resin places a layer over the hydrogen bonds formed between adjacent paper fibers and thus prevents water from breaking the hydrogen bonds.
  • wet-strength agents suitable for use herein include compounds made of epichlorohydrin adducts of polyamines, polyethyleneimines, cationic starches, polydiallyldimethylammonium chloride, and mixtures thereof, amine- aldehyde resins such as melamine-formaldehyde resin, amide-aldehyde resins, and mixtures thereof.
  • amine- aldehyde resins such as melamine-formaldehyde resin, amide-aldehyde resins, and mixtures thereof.
  • the preferred components are the polymeric amine-epichlorohydrin resins selected from the group consisting of a polyamide-epichlorohydrin (PAE) resin, a polyalkylenepolyamine-epichlorohydrin (PAPAE) resin, and an amine polymer- epichlorohydrin (APE) resin, in which the amine groups have been alkylated with epichlorohydrin to produce a polyamine-epichlorohydrin resin that has azetidinium or epoxide functionality.
  • PAE polyamide-epichlorohydrin
  • PAPAE polyalkylenepolyamine-epichlorohydrin
  • APE amine polymer- epichlorohydrin
  • the cross-linking resin having cationic properties is a cationic wet strength resin that is produced by reacting a saturated aliphatic dicarboxylic acid containing three to ten carbon atoms with a polyalkylenepolyamine, containing from two to four ethylene groups, two primary amine groups, and one to three secondary amine groups (such as diethylenetriamine, triethylenetetramine and tetraethylenepentamine), to form a poly(aminoamide) having secondary amine groups that are alkylated with epichlorohydrin to form a PAE resin.
  • a saturated aliphatic dicarboxylic acid containing three to ten carbon atoms with a polyalkylenepolyamine, containing from two to four ethylene groups, two primary amine groups, and one to three secondary amine groups (such as diethylenetriamine, triethylenetetramine and tetraethylenepentamine), to form a poly(aminoamide) having secondary amine groups that are alkylated with epic
  • cross-linking resin having cationic properties from this class are the wet strength resin Kymene 557H (available from Hercules Incorporated), in which adipic acid is reacted with diethylenetriamine to form a poly(aminoamide) that is alkylated and crosslinked with epichlorohydrin to form a PAE resin.
  • Still another preferred cross-linking resin having cationic properties made of epichlorohydrin are Luresin.RTM and Etadu n which both are polyamidoamine- epichlorohydrin resins.
  • Amine-aldehyde resins are suitable cross-linking resins for the present invention and are made by condensation of amine or amide monomers with aldehydes such as formaldehyde or glyoxal.
  • Preferred amines are those having low molecular weight amines e.g. melamine or polymeric amines e.g. poly- diallylamine, preferably quartemized.
  • Preferred amides are those polymeric amides such as polyacrylamide. All these suitable amine/amide monomers can also be copolymerized with cationic monomers.
  • amine-aldehyde cross-linking resin preferred are those from the class of melamine-formaldehyde resin.
  • Melamine-formaldehyde resins of this type are known as crosslinking agents of this type in the coating industry and are also described, for example, in German Auslegeschrift Nos. 2,457,387 (U.S. Pat. No. 4,035,213 incorporated herein by reference) and 1 ,719,324 and, in particular, in U.S. Pat. No. 3,242,230 incorporated herein by reference.
  • Preferred melamine-formaldehyde resin are those commercially available under the tradenames Madurit, and Cassurit from Clariant.
  • Still other preferred cross-linking resin having the property of being cationic among the class of amine-aldehyde cross-linking resin are the Poly(acrylamide- glyoxal) resin commercially available under the tradename SOLIDURIT KM from Clariant.
  • the cross-linking resin having cationic properties have a molecular weight between 200 and 1 ,000,000, preferably between 500 and 100,000, most preferably between 1000 and 25,000.
  • Cross- linking resin having a low molecular weight are most preferred for use in the present invention as they are more water-soluble and have a better fiber penetration.
  • low molecular weight it is meant a molecular weight within the range of from 25 to 2000, preferably from 50 to 1000, and more preferably from 50 to 500.
  • cross-linking components may be used in a composition for delivery onto fabric, such as by means of a rinse process.
  • the level of cross-linking components or derivative thereof is present in an amount of from 0.01 % to 60%, preferably from 0.01 % to 30% by weight of the total composition
  • catalysts includes organic acids such as citric acid, succinic acid, and tartaric acids, as well as conventional Lewis acid such as Al Cl 3 or MgCI 2 , or salts thereof, or mixtures thereof.
  • organic acids such as citric acid, succinic acid, and tartaric acids
  • Lewis acid such as Al Cl 3 or MgCI 2
  • catalyst NKD made of a mixture of salts and organic acid, and commercially available from Hoechst.
  • the level of catalyst is from 10% to 50%, preferably from 20 to 40% by weight of the cross-linking components or derivative thereof.
  • composition of the invention also contains a fabric softening compound.
  • Typical levels of incorporation of the softening compound in the composition are of from 1 % to 80% by weight, preferably from 2% to 70%, more preferably from 5% to 60%, by weight of the composition.
  • Typical of the cationic softening components are the quaternary ammonium compounds or amine precursors thereof as defined hereinafter.
  • AV-Quaternarv Ammonium Fabric Softening Active Compound (1 ) Preferred quaternary ammonium fabric softening active compound have the formula
  • each R unit is independently hydrogen, C-i-Cg alkyl, C-
  • R2 is hydrogen, C1-C4 alkyl, C-1-C4 hydroxyalkyl, and mixtures thereof;
  • X is an anion which is compatible with fabric softener actives and adjunct ingredients;
  • the index m is from 1 to 4, preferably 2;
  • the index n is from 1 to 4, preferably 2.
  • An example of a preferred fabric softener active is a mixture of quaternized amines having the formula:
  • R is preferably methyl;
  • Rl is a linear or branched alkyl or alkenyl chain comprising at least 11 atoms, preferably at least 15 atoms.
  • the unit -O2CRI represents a fatty acyl unit which is typically derived from a triglyceride source.
  • the triglyceride source is preferably derived from tallow, partially hydrogenated tallow, lard, partially hydrogenated lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil, etc. and mixtures of these oils.
  • the preferred fabric softening actives of the present invention are the Diester and/or Diamide Quaternary Ammonium (DEQA) compounds, the diesters and diamides having the formula:
  • R is preferably methyl, Q and R 1 are as defined herein before; followed by quaternization to the final softener active.
  • Non-limiting examples of preferred amines which are used to form the DEQA fabric softening actives according to the present invention include methyl bis(2- hydroxyethyl)amine having the formula:
  • the counterion, ⁇ ( ' ) above can be any softener-compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and the like, more preferably chloride or methyl sulfate.
  • the anion can also, but less preferably, carry a double charge in which case ⁇ ( " ) represents half a group.
  • Tallow and canola oil are convenient and inexpensive sources of fatty acyl units which are suitable for use in the present invention as R1 units.
  • the following are non-limiting examples of quaternary ammonium compounds suitable for use in the compositions of the present invention.
  • the term "tallowyl” as used herein below indicates the R-* unit is derived from a tallow triglyceride source and is a mixture of fatty alkyl or alkenyl units.
  • canolyl refers to a mixture of fatty alkyl or alkenyl units derived from canola oil.
  • Fabric Softener Actives N,N-di(tallowyl-oxy-2-oxo-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium chloride;
  • quatemay ammoniun softening compounds are methylbis(tallowamidoethyl)(2-hydroxyethyl)ammonium methylsulfate and methylbis(hydrogenated tallowamidoethyl)(2-hydroxyethyl)ammonium methylsulfate; these materials are available from Witco Chemical Company under the trade names Varisoft® 222 and Varisoft® 110, respectively.
  • the level of unsaturation contained within the tallow, canola, or other fatty acyl unit chain can be measured by the Iodine Value (IV) of the corresponding fatty acid, which in the present case should preferably be in the range of from 5 to 100 with two categories of compounds being distinguished, having a IV below or above 25.
  • IV Iodine Value
  • a cis/trans isomer weight ratio greater than about 30/70, preferably greater than about 50/50 and more preferably greater than about 70/30 provides optimal concentrability.
  • R units are preferably methyl, however, suitable fabric softener actives are described by replacing the term "methyl” in the above examples in Table II with the units "ethyl, ethoxy, propyl, propoxy, isopropyl, butyl, isobutyl and t-butyl.
  • the counter ion, X in the examples of Table II can be suitably replaced by bromide, methylsulfate, formate, sulfate, nitrate, and mixtures thereof.
  • the anion, X is merely present as a counterion of the positively charged quaternary ammonium compounds. The scope of this invention is not considered limited to any particular anion.
  • the pH of the compositions herein is an important parameter of the present invention. Indeed, it influences the stability of the quaternary ammonium or amine precursors compounds, especially in prolonged storage conditions.
  • the diester when specified, it will include the monoester that is normally present in manufacture. For softening, under no/low detergent carry-over laundry conditions the percentage of monoester should be as low as possible, preferably no more than about 2.5%. However, under high detergent carry-over conditions, some monoester is preferred.
  • the overall ratios of diester to monoester are from about 100:1 to about 2:1 , preferably from about 50:1 to about 5:1 , more preferably from about 13:1 to about 8:1. Under high detergent carry-over conditions, the di/monoester ratio is preferably about 11 :1.
  • the level of monoester present can be controlled in the manufacturing of the softener compound.
  • Mixtures of actives of formula (1 ) and (2) may also be prepared.
  • quaternary ammonium fabric softening compounds for use herein are cationic nitrogenous salts having two or more long chain acyclic aliphatic C8-C22 hydrocarbon groups or one said group and an arylalkyl group which can be used either alone or as part of a mixture are selected from the group consisting of:
  • R4 is an acyclic aliphatic C8-C22 hydrocarbon group
  • R ⁇ is a C-1-C4 saturated alkyl or hydroxyalkyl group
  • Fl ⁇ is selected from the group consisting of R4 and R5 groups
  • A- is an anion defined as above;
  • n is equal to 1 to about 5, and R1 , R2, R5 and A" are as defined above; (iii) mixtures thereof.
  • Examples of the above class cationic nitrogenous salts are the well-known dialkyldi methylammonium salts such as ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, di(hydrogenatedtallow)dimethylammonium chloride, distearyldimethylammonium chloride, dibehenyldimethylammonium chloride. Di(hydrogenatedtallow)di methylammonium chloride and ditallowdimethylammonium chloride are preferred.
  • dialkyldimethyl ammonium salts examples include di(hydrogenatedtallow)dimethylammonium chloride (trade name Adogen® 442), ditallowdimethylammonium chloride (trade name Adogen® 470, Praepagen® 3445), distearyl dimethylammonium chloride (trade name Arosurf® TA-100), all available from Witco Chemical Company.
  • Dibehenyldimethylammonium chloride is sold under the trade name Kemamine Q-2802C by Humko Chemical Division of Witco Chemical Corporation.
  • Dimethylstearylbenzyl ammonium chloride is sold under the trade names Varisoft ® SDC by Witco Chemical Company and Ammonyx® 490 by Onyx Chemical Company.
  • Suitable amine fabric softening compounds for use herein, which may be in amine form or cationic form are selected from:
  • the preferred Component (i) is a nitrogenous compound selected from the group consisting of the reaction product mixtures or some selected components of the mixtures.
  • One preferred component (i) is a compound selected from the group consisting of substituted imidazoline compounds having the formula:
  • R 7 is an acyclic aliphatic C-15-C21 hydrocarbon group and R 8 is a divalent C1-C3 alkylene group.
  • Component (i) materials are commercially available as: Mazamide® 6, sold by Mazer Chemicals, or Ceranine® HC, sold by Sandoz Colors & Chemicals; stearic hydroxyethyl imidazoline sold under the trade names of Alkazine® ST by Alkaril Chemicals, Inc., or Schercozoline® S by Scher Chemicals, Inc.; N,N"- ditallowalkoyldiethylenetriamine; 1 -tallowamidoethyl-2-tallowimidazoline (wherein in the preceding structure R " * is an aliphatic C-15-C17 hydrocarbon group and R ⁇ is a divalent ethylene group).
  • N,N"-ditallowalkoyldiethylenetriamine and 1-tallow(amidoethyl)-2- tallowimidazoline are reaction products of tallow fatty acids and diethylenetriamine, and are precursors of the cationic fabric softening agent methyl-1-taIlowamidoethyl-2-tallowimidazolinium methylsulfate (see "Cationic Surface Active Agents as Fabric Softeners," R. R. Egan, Journal of the American Oil Chemicals' Society, January 1978, pages 118-121).
  • N,N"-ditallow alkoyldiethylenetriamine and 1-tallowamidoethyl-2-tallowimidazoline can be obtained from Witco Chemical Company as experimental chemicals.
  • Methyl-1- tallowamidoethyl-2-tallowimidazolinium methylsulfate is sold by Witco Chemical Company under the tradename Varisoft® 475.
  • each R 2 is a C-]_6 alkylene group, preferably an ethylene group; and G is an oxygen atom or an -NR- group; and each R, R 1 , R 2 and R have the definitions given above and A " has the definitions given above for X " .
  • An example of Compound (ii) is 1-oleylamidoethyl-2-oleylimidazolinium chloride wherein R " - is an acyclic aliphatic C15-C17 hydrocarbon group, R2 is an ethylene group, G is a NH group, R5 is a methyl group and A- is a chloride anion.
  • R, R1 , R2, and A are defined as above.
  • R " - is derived from oleic acid
  • softening active can also encompass mixed softening active agents.
  • Preferred among the classes of softener compounds disclosed herein before are the diester or diamido quaternary ammonium fabric softening active compound
  • Fully formulated fabric softening compositions may contain, in addition to the hereinbefore described components, one or more of the following ingredients.
  • the liquid carrier employed in the instant compositions is preferably at least primarily water due to its low cost, relative availability, safety, and environmental compatibility.
  • the level of water in the liquid carrier is preferably at least about 50%, most preferably at least about 60%, by weight of the carrier.
  • Mixtures of water and low molecular weight, e.g., ⁇ about 200, organic solvent, e.g., lower alcohols such as ethanol, propanol, isopropanol or butanol are useful as the carrier liquid.
  • Low molecular weight alcohols include monohydric, dihydric (glycol, etc.) trihydric (glycerol, etc.), and higher polyhydric (polyols) alcohols.
  • compositions containing both saturated and unsaturated diester quaternary ammonium compounds can be prepared that are stable without the addition of concentration aids.
  • the compositions of the present invention may require organic and/or inorganic concentration aids to go to even higher concentrations and/or to meet higher stability standards depending on the other ingredients.
  • concentration aids which typically can be viscosity modifiers may be needed, or preferred, for ensuring stability under extreme conditions when particular softener active levels are used.
  • the surfactant concentration aids are typically selected from the group consisting of (1) single long chain alkyl cationic surfactants; (2) nonionic surfactants; (3) amine oxides; (4) fatty acids; and (5) mixtures thereof.
  • the total level is from 0.1 % to 20%, preferably from 0.2% to 10%, more preferably from 0.5% to 5%, and even more preferably from 1 % to 2% by weight of the composition.
  • These materials can either be added as part of the active softener raw material, (I), e.g., the mono- long chain alkyl cationic surfactant and/or the fatty acid which are reactants used to form the biodegradable fabric softener active as discussed hereinbefore, or added as a separate component.
  • the total level of dispersibility aid includes any amount that may be present as part of component (I).
  • Inorganic viscosity/dispersibility control agents which can also act like or augment the effect of the surfactant concentration aids, include water-soluble, ionizable salts which can also optionally be incorporated into the compositions of the present invention.
  • ionizable salts can be used. Examples of suitable salts are the halides of the Group IA and IIA metals of the Periodic Table of the Elements, e.g., calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride.
  • the ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein, and later to obtain the desired viscosity.
  • the amount of ionizable salts used depends on the amount of active ingredients used in the compositions and can be adjusted according to the desires of the formuiator. Typical levels of salts used to control the composition viscosity are from about 20 to about 20,000 parts per million (ppm), preferably from about 20 to about 11 ,000 ppm, by weight of the composition.
  • Alkylene polyammonium salts can be incorporated into the composition to give viscosity control in addition to or in place of the water-soluble, ionizable salts above.
  • these agents can act as scavengers, forming ion pairs with anionic detergent carried over from the main wash, in the rinse, and on the fabrics, and may improve softness performance. These agents may stabilize the viscosity over a broader range of temperature, especially at low temperatures, compared to the inorganic electrolytes.
  • Specific examples of alkylene polyammonium salts include l-lysine monohydrochloride and 1 ,5-diammonium 2-methyl pentane dihydrochloride. Pi-Stabilizers
  • Stabilizers can be present in the compositions of the present invention.
  • the term "stabilizer,” as used herein, includes antioxidants and reductive agents. These agents are present at a level of from 0% to about 2%, preferably from about 0.01 % to about 0.2%, more preferably from about 0.035% to about 0.1 % for antioxidants, and more preferably from about 0.01 % to about 0.2% for reductive agents. These assure good odor stability under long term storage conditions for the compositions and compounds stored in molten form.
  • the use of antioxidants and reductive agent stabilizers is especially critical for low scent products (low perfume).
  • antioxidants examples include a mixture of ascorbic acid, ascorbic palmitate, propyl gallate, available from Eastman Chemical Products, Inc., under the trade names Tenox® PG and Tenox S-1 ; a mixture of BHT (butylated hydroxytoluene), BHA (butylated hydroxyanisole), propyl gallate, and citric acid, available from Eastman Chemical Products, Inc., under the trade name Tenox-6; butylated hydroxytoluene, available from UOP Process Division under the trade name Sustane® BHT; tertiary butylhydroquinone, Eastman Chemical Products, Inc., as Tenox TBHQ; natural tocopherols, Eastman Chemical Products, Inc., as Tenox GT-1/GT-2; and butylated hydroxyanisole, Eastman Chemical Products, Inc., as BHA; long chain esters (C8-C22) o gallic acid, e.g., dodecyl
  • Irganox® B 1171 Irganox® 1425; Irganox® 3114; Irganox® 3125; and mixtures thereof; preferably Irganox® 3125, Irganox® 1425, Irganox® 3114, and mixtures thereof; more preferably Irganox® 3125 alone.
  • the chemical names and CAS numbers for some of the above stabilizers are listed in Table II below.
  • Irganox® 1098 23128-74-7 N.N'-Hexamethylene bis(3,5-di-tert-butyl-4- hydroxyhydrocinnamamide Irganox® B 1171 31570-04-4
  • reductive agents examples include sodium borohydride, hypophosphorous acid, Irgafos® 168, and mixtures thereof.
  • composition may suitably use an optional solubilized, water-soluble antimicrobial active, useful in providing protection against organisms that become attached to the treated material.
  • an optional solubilized, water-soluble antimicrobial active useful in providing protection against organisms that become attached to the treated material.
  • the free, uncomplexed antimicrobial, e.g., antibacterial, active provides an optimum antibacterial performance.
  • compositions of the present invention containing, antimicrobial materials, e.g., antibacterial halogenated compounds, quaternary compounds, and phenolic compounds.
  • antimicrobial materials e.g., antibacterial halogenated compounds, quaternary compounds, and phenolic compounds.
  • Some of the more robust antimicrobial halogenated compounds which can function as disinfectants/sanitizers as well as finish product preservatives (vide infra), and are useful in the compositions of the present invention include 1 ,1'-hexamethylene bis(5-(p-chlorophenyl)biguanide), commonly known as chlorhexidine, and its salts, e.g., with hydrochloric, acetic and gluconic acids.
  • the digluconate salt is highly water-soluble, about 70% in water, and the diacetate salt has a solubility of about 1.8% in water.
  • chlorhexidine When chlorhexidine is used as a sanitizer in the present invention it is typically present at a level of from about 0.001% to about 0.4%, preferably from about 0.002% to about 0.3%, and more preferably from about 0.01 % to about 0.1 %, by weight of the usage composition. In some cases, a level of from about 1 % to about 2% may be needed for virucidal activity.
  • Other useful biguanide compounds include Cosmoci® CQ®, Vantocil® IB, including poly (hexamethylene biguanide) hydrochloride.
  • Other useful cationic antimicrobial agents include the bis-biguanide alkanes.
  • Usable water soluble salts of the above are chlorides, bromides, sulfates, alkyl sulfonates such as methyl sulfonate and ethyl sulfonate, phenylsulfonates such as p-methylphenyl sulfonates, nitrates, acetates, gluconates, and the like.
  • the bis biguanide of choice is chlorhexidine and its salts, e.g., digluconate, dihydrochloride, diacetate, and mixtures thereof.
  • Quaternary Compounds A wide range of quaternary compounds can also be used as antimicrobial actives, in conjunction with the preferred surfactants, for compositions of the present invention that do not contain cyclodextrin.
  • useful quaternary compounds include: (1 ) benzalkonium chlorides and/or substituted benzalkonium chlorides such as commercially available Barquat® (available from Lonza), Maquat® (available from Mason), Variquat® (available from Witco/Sherex), and Hyamine® (available from Lonza); (2) dialkyl quaternary such as Bardac® products of Lonza, (3) N-(3-chloroallyl) hexaminium chlorides such as Dowicide® and Dowicil® available from Dow; (4) benzethonium chloride such as Hyamine® 1622 from Rohm & Haas; (5) methylbenzethonium chloride represented by Hyamine® 10X supplied by Rohm & Haas, (6) cet
  • Typical concentrations for biocidal effectiveness of these quaternary compounds range from about 0.001 % to about 0.8%, preferably from about 0.005% to about 0.3%, more preferably from about 0.01 % to 0.2%, by weight of the usage composition.
  • the corresponding concentrations for the concentrated compositions are from about 0.003% to about 2%, preferably from about 0.006% to about 1.2%, and more preferably from about 0.1% to about 0.8% by weight of the concentrated compositions.
  • the present invention can contain a perfume. Suitable perfumes are disclosed in U.S. Pat. 5,500,138, said patent being incorporated herein by reference.
  • perfume includes fragrant substance or mixture of substances including natural (i.e., obtained by extraction of flowers, herbs, leaves, roots, barks, wood, blossoms or plants), artificial (i.e., a mixture of different nature oils or oil constituents) and synthetic (i.e., synthetically produced) odoriferous substances.
  • natural i.e., obtained by extraction of flowers, herbs, leaves, roots, barks, wood, blossoms or plants
  • artificial i.e., a mixture of different nature oils or oil constituents
  • synthetic i.e., synthetically produced
  • perfumes are complex mixtures of a plurality of organic compounds.
  • perfume ingredients useful in the perfumes of the present invention compositions include, but are not limited to, hexyl cinnamic aldehyde; amyl cinnamic aldehyde; amyl salicylate; hexyl salicylate; terpineol; 3,7-dimethyl-c/s-
  • 3-octanol 3,7-dimethyl-frans-2,6-octadien-1-ol; 3,7-dimethyl-6-octen-1-ol; 3,7- dimethyl-1 -octanol; 2-methyl-3-(para-tert-butylphenyl)-propionaldehyde; 4-(4- hydroxy-4-methylpentyl)-3-cyclohexene-1 -carboxaldehyde; tricyclodecenyl propionate; tricyclodecenyl acetate; anisaldehyde; 2-methyl-2-(para-iso- propylphenyl)-propionaldehyde; ethyl-3-methyl-3-phenyl glycidate; 4-(para- hydroxyphenyl)-butan-2-one; 1 -(2,6,6-trimethyl-2-cyclohexen-1 -yl)-2-buten-1 -one; para-methoxyacetophenone
  • fragrance materials include, but are not limited to, orange oil; lemon oil; grapefruit oil; bergamot oil; clove oil; dodecalactone gamma; methyl-2-(2-pentyl-3-oxo-cyclopentyl) acetate; beta-naphthol methylether; methyl-beta-naphthylketone; coumarin; decylaldehyde; benzaldehyde; 4-tert- butylcyclohexyl acetate; alpha, alpha-dimethylphenethyl acetate; methylphenylcarbinyl acetate; Schiffs base of 4-(4-hydroxy-4-methylpentyl)-3- cyclohexene-1 -carboxaldehyde and methyl anthranilate; cyclic ethyleneglycol diester of tridecandioic acid; 3,7-dimethyl-2,6-octadiene-1-nitrile;
  • indane 5-acetyl-3-isopropyl-1 ,1 ,2,6-tetramethyl indane; 1-dodecanal; 7-hydroxy-3,7-dimethyl octanal; 10-undecen-1-al; iso- hexenyl cyclohexyl carboxaldehyde; formyl tricyclodecan; cyclopentadecanolide; 16-hydroxy-9-hexadecenoic acid lactone; 1 ,3,4,6,7,8-hexahydro-4,6,6,7,8,8- hexamethylcyclopenta-gamma-2-benzopyrane; ambroxane; dodecahydro- 3a,6,6,9a-tetramethylnaphtho-[2,1 bjfuran; cedrol; 5-(2,2,3-trimethylcyclopent-3- enyl)-3-methylpentan-2-ol; 2-ethyl-4-(2,2,3-
  • perfume components are geraniol; geranyl acetate; linalool; linalyl acetate; tetrahydrolinalool; citronellol; citronellyl acetate; dihydromyrcenol; dihydromyrcenyl acetate; tetrahydromyrcenol; terpinyl acetate; nopol; nopyl acetate; 2-phenylethanol; 2-phenylethyl acetate; benzyl alcohol; benzyl acetate; benzyl salicylate; benzyl benzoate; styrallyl acetate; dimethylbenzylcarbinol; trichloromethylphenylcarbinyl methylphenylcarbinyl acetate; isononyl acetate; vetiveryl acetate; vetiverol; 2-methyl-3-(p-tert-butylphenyl)-propanal; 2-methyl-3-(
  • the perfumes useful in the present invention compositions are substantially free of halogenated materials and nitromusks.
  • Suitable solvents, diluents or carriers for perfumes ingredients mentioned above are for examples, ethanol, isopropanol, diethylene glycol, monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, etc.
  • the amount of such solvents, diluents or carriers incorporated in the perfumes is preferably kept to the minimum needed to provide a homogeneous perfume solution.
  • Perfume can be present at a level of from 0% to 10%, preferably from 0.1 % to 5%, and more preferably from 0.2% to 3%, by weight of the finished composition.
  • Fabric softener compositions of the present invention provide improved fabric perfume deposition.
  • Perfume ingredients may also be suitably added as releasable fragrances, for example, as pro-perfumes or pro-fragrances as described in U.S. 5,652,205 Hartman et al., issued July 29, 1997, WO95/04809, WO96/02625, PCT US97/14610 filed 19 August 1997 and claiming priority of 19 August 1996, and EP-A-0,752,465, incorporated herein by reference.
  • Soil Release agents are desirably used in compositions of the instant invention. Any polymeric soil release agent known to those skilled in the art can optionally be employed in the compositions of this invention. Polymeric soil release agents are characterized by having both hydrophilic segments, to hydrophilize the surface of hydrophobic fibers, such as polyester and nylon, and hydrophobic segments, to deposit upon hydrophobic fibers and remain adhered thereto through completion of washing and rinsing cycles and, thus, serve as an anchor for the hydrophilic segments. This can enable stains occurring subsequent to treatment with the soil release agent to be more easily cleaned in later washing procedures.
  • soil release agents will generally comprise from about 0.01% to about 10.0%, by weight, of the detergent compositions herein, typically from about 0.1 % to about 5%, preferably from about 0.2% to about 3.0%.
  • soil release agents include the METOLOSE SM100, METOLOSE SM200 manufactured by Shin-etsu Kagaku Kogyo K.K., SOKALAN type of material, e.g., SOKALAN HP-22, available from BASF (Germany), ZELCON 5126 (from Dupont) and MILEASE T (from ICI).
  • compositions according to the present invention are preferably greater than 3, preferably between 3 and 12. This range is preferred for fabric safety.
  • a lubricant of the diester quaternary ammonium type it is most preferred to have the conventional pH range, as measured in the neat compositions at 20 °C, of from 2.0 to 5, preferably in the range of 2.5 to 4.5, preferably about 2.5 to about 3.5.
  • the pH of these compositions herein can be regulated by the addition of a Bronsted acid.
  • the present invention can include optional components conventionally used in textile treatment compositions, for example, colorants, preservatives, bactericides, optical brighteners, opacifiers, anti-shrinkage agents, germicides, fungicides, anti-oxidants, dye fixing agent, enzymes, chelating agents, cyclodextrin, metallic salts to absorb amine and sulfur-containing compounds and selected from the group consisting of copper salts, zinc salts, and mixtures thereof, color protectors like polyethylene imine and its alkoxylated derivatives, 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.
  • composition or its individual components can be provided in any suitable form such as spray, foam, gel or any other suitable form for liquid aqueous compositions.
  • a method of treating fabrics in particular to provide durable press on fabric, i.e. for providing wrinkle resistant fabrics, which comprises the steps of contacting the fabrics with a cross-linking compound or composition of the invention, as defined herein before, and subsequently curing the composition using a domestic process.
  • contacting it is meant any steps that is suitable for providing a contact of the composition with the fabric. This can include by soaking, washing, rinsing, and/or spraying as well as by means of a dryer sheet onto which is adsorbed the composition.
  • the contacting occurs in the step of a laundering process, preferably a rinse step of a laundry process, which more preferably occurs at a temperature range below 30°C, preferably between 5 and 25°C.
  • Domestic curing of the fabric can be caused by the heat used to dry the fabric, e.g. by tumble drying. Ironing is also particularly advantageous for curing the fabric. Without to be bound by theory, it is believed that the shorter time or the low temperatures used to domestically cure the cross-linking components mean that the fabric is made resistant to wrinkles without changing its tactile, or drape properties. Still another advantage of the present invention is that when epichlorhydrin adducts of polyamine resins, polyethyleneimine resins, cationic starch, or polydiallyldimethylammonium . chloride are used, such as in particular with Kymene compounds, the domestic curing can occur at room temperature, i.e. from 15 to 30°C.
  • epichlorhydrin adducts are their usability in industrial treatment. Accordingly, there is also provided a method for treating fabric which comprises the steps of contacting the fabrics with an epichlorhydrin adduct of polyamine resins, polyethyleneimine resins, cationic starch, or polydiallyldimethylammonium chloride, or mixtures thereof, and thereafter curing the fabrics.
  • the curing is that which is conventionally known in industrial process like padding.
  • 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.
  • Still another preferred way of treating the fabrics is when the fabric can be sprayed with an effective amount of the composition, allowed to dry and then ironed, or sprayed and ironed immediately.
  • Resin #1 Polyamide/polyamine/epichlorohydrin resin commercially available under the tradename KYMENE 557 from Hercules
  • Resin #3 Melamine-formaldehyde resin commercially available under the tradename CASSURIT HML from Clariant
  • Resin #4 Poly(acrylamide-glyoxal) resin commercially available under the tradename SOLIDURIT KM from Clariant
  • Resin #5 Melamine-formaldehyde resin commercially available under the tradename MADURIT MW 167 from Clariant
  • Catalyst Catalyst NKD made of a mixture of salts and organic acid, and commercially available from Hoechst
  • DOEQA Di-(oleyioxyethyl) dimethyl ammonium methylsulfate
  • PEI 1800 E1 Ethoxylated polyethylene imine (MW 1800, at 50% active) as synthesised in Synthesis example 1
  • PEI 1200 E7 Ethoxylated polyethylene imine (MW 1200, at 50% active in water) as synthesised per Synthesis example 2
  • Dye Fix 1 Cellulose reactive dye fixing agent available under the tradename Indosol CR from Clariant
  • Step A)-The ethoxylation is conducted in a 2 gallon stirred stainless steel autoclave equipped for temperature measurement and control, pressure measurement, vacuum and inert gas purging, sampling, and for introduction of ethylene oxide as a liquid.
  • a -20 lb. net cylinder of ethylene oxide (ARC) is set up to deliver ethylene oxide as a liquid by a pump to the autoclave with the cylinder placed on a scale so that the weight change of the cylinder could be monitored.
  • a 750 g portion of polyethyleneimine (PEI) (Nippon Shokubai, Epomin SP-018 having a listed average molecular weight of 1800 equating to 0.417 moles of polymer and 17.4 moles of nitrogen functions) is added to the autoclave.
  • the autoclave is then sealed and purged of air (by applying vacuum to minus 28" Hg followed by pressurization with nitrogen to 250 psia, then venting to atmospheric pressure).
  • the autoclave contents are heated to 130 °C while applying vacuum.
  • the autoclave is charged with nitrogen to about 250 psia while cooling the autoclave to about 105 °C.
  • Ethylene oxide is then added to the autoclave incrementally over time while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate.
  • the ethylene oxide pump is turned off and cooling is applied to limit any temperature increase resulting from any reaction exotherm.
  • the temperature is maintained between 100 and 110 °C while the total pressure is allowed to gradually increase during the course of the reaction.
  • Step B)- The reaction mixture is then deodorized by passing about 100 cu. ft. of inert gas (argon or nitrogen) through a gas dispersion frit and through the reaction mixture while agitating and heating the mixture to 130 °C.
  • inert gas argon or nitrogen
  • the final reaction product is cooled slightly and collected in glass containers purged with nitrogen.
  • Synthesis Example 2 Preparation of PEI 1200 Ej ⁇ Step A)-The ethoxylation is conducted in a 2 gallon stirred stainless steel autoclave equipped for temperature measurement and control, pressure measurement, vacuum and inert gas purging, sampling, and for introduction of ethylene oxide as a liquid.
  • a -20 lb. net cylinder of ethylene oxide (ARC) is set up to deliver ethylene oxide as a liquid by a pump to the autoclave with the cylinder placed on a scale so that the weight change of the cylinder could be monitored.
  • PEI polyethyleneimine
  • the autoclave is then sealed and purged of air (by applying vacuum to minus 28" Hg followed by pressurization with nitrogen to 250 psia, then venting to atmospheric pressure).
  • the autoclave contents are heated to 130 °C while applying vacuum.
  • the autoclave is charged with nitrogen to about 250 psia while cooling the autoclave to about 105 °C.
  • Ethylene oxide is then added to the autoclave incrementally over time while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate.
  • the ethylene oxide pump is turned off and cooling is applied to limit any temperature increase resulting from any reaction exotherm.
  • the temperature is maintained between 100 and 110 °C while the total pressure is allowed to gradually increase during the course of the reaction.
  • the temperature is increased to 110 °C and the autoclave is allowed to stir for an additional hour. At this point, vacuum is applied to remove any residual unreacted ethylene oxide.
  • Step B)- The reaction mixture is then deodorized by passing about 100 cu. ft. of inert gas (argon or nitrogen) through a gas dispersion frit and through the reaction mixture while agitating and heating the mixture to 130 °C.
  • inert gas argon or nitrogen
  • the final reaction product is cooled slightly and collected in glass containers purged with nitrogen. In other preparations the neutralization and deodorization is accomplished in the reactor before discharging the product.
  • Step A and B Vacuum is continuously applied while the autoclave is cooled to about 50 °C while introducing 376 g of a 25% sodium methoxide in methanol solution (1.74 moles, to achieve a 10% catalyst loading based upon PEI nitrogen functions).
  • the methoxide solution is sucked into the autoclave under vacuum and then the autoclave temperature controller setpoint is increased to 130 °C.
  • a device is used to monitor the power consumed by the agitator. The agitator power is monitored along with the temperature and pressure.
  • Agitator power and temperature values gradually increase as methanol is removed from the autoclave and the viscosity of the mixture increases and stabilizes in about 1 hour indicating that most of the methanol has been removed.
  • the mixture is further heated and agitated under vacuum for an additional 30 minutes.
  • Vacuum is removed and the autoclave is cooled to 105 °C while it is being charged with nitrogen to 250 psia and then vented to ambient pressure.
  • the autoclave is charged to 200 psia with nitrogen.
  • Ethylene oxide is again added to the autoclave incrementally as before while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate while maintaining the temperature between 100 and 110 °C and limiting any temperature increases due to reaction exotherm.
  • 4500 g of ethylene oxide resulting in a total of 7 moles of ethylene oxide per mole of PEI nitrogen function
  • the temperature is increased to 110 °C and the mixture stirred for an additional hour.
  • reaction mixture is then collected in nitrogen purged containers and eventually transferred into a 22 L three neck round bottomed flask equipped with heating and agitation.
  • the strong alkali catalyst is neutralized by adding 167 g methane sulfonic acid (1.74 moles).
  • PEI 1200 E2, PEI 1200 E3, PEI 1200 E15 and PEI 1200 E20 can be prepared by the above method by adjusting the reaction time and the relative amount of ethylene oxide used in the reaction.
  • compositions A to J are in accordance with the invention.

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Abstract

L'invention concerne une composition ainsi qu'un procédé pour traiter des tissus en vue d'améliorer diverses propriétés de ceux-ci, notamment leur résistance au froissement, au moyen d'une résine de réticulation présentant des propriétés cationiques.
PCT/US1999/017554 1998-08-03 1999-08-03 Composition conferant une resistance au froissement WO2000008127A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BR9912708-3A BR9912708A (pt) 1998-08-03 1999-08-03 Composição resistente ao enrugamento
CA002338791A CA2338791A1 (fr) 1998-08-03 1999-08-03 Composition conferant une resistance au froissement
JP2000563754A JP2002522650A (ja) 1998-08-03 1999-08-03 しわ防止組成物
US09/762,080 US6514932B1 (en) 1998-08-03 1999-08-03 Wrinkle resistant composition
AU53328/99A AU5332899A (en) 1998-08-03 1999-08-03 Wrinkle resistant composition

Applications Claiming Priority (2)

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EP98870173.6 1998-08-03
EP98870173A EP0978556B1 (fr) 1998-08-03 1998-08-03 Composition pour rendre infroissable

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WO2000008127A1 true WO2000008127A1 (fr) 2000-02-17

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AT (1) ATE278758T1 (fr)
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CA (1) CA2338791A1 (fr)
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Cited By (5)

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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
US6569823B2 (en) 2000-04-14 2003-05-27 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Fabric care composition
JP2003525357A (ja) * 2000-02-25 2003-08-26 ビーエーエスエフ アクチェンゲゼルシャフト セルロース−含有織物の防しわ最終仕上げ、および洗濯用後処理剤
US7429558B2 (en) 2002-01-18 2008-09-30 Unilever Home & Personal Care Division Of Conopco, Inc. Azetidinium modified polymers and fabric treatment composition

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Publication number Priority date Publication date Assignee Title
US6514932B1 (en) 1998-08-03 2003-02-04 Procter & Gamble Company Wrinkle resistant composition
BR0008373A (pt) * 1999-02-19 2001-11-06 Procter & Gamble Composições de intensificação de tecido
EP1096056A1 (fr) * 1999-10-27 2001-05-02 The Procter & Gamble Company Composition pour rendre infroissable
US6551986B1 (en) 2000-02-16 2003-04-22 The Procter & Gamble Company Fabric enhancement compositions
DE10060373A1 (de) * 2000-12-05 2002-06-06 Basf Ag Reaktiv modifizierte, teilchenförmige Polymerisate zur Behandlung der Oberflächen textiler und nicht-textiler Materialien
ES2276851T3 (es) * 2000-12-11 2007-07-01 Unilever Plc Mejoras en el cuidado de telas.
DE10150724A1 (de) 2001-03-03 2003-04-17 Clariant Gmbh Waschmittel und Wäschebehandlungsmittel enthaltend ein oder mehrere farbübertragungsinhibierende Farbfixiermittel
EP1239025A3 (fr) 2001-03-03 2003-09-03 Clariant GmbH Composition détergente et composition de traitement du linge comprenant un agent inhibant le transfert des couleurs et fixant les couleurs
DE10124387A1 (de) 2001-05-18 2002-11-28 Basf Ag Hydrophob modifizierte Polyethylenimine und Polyvinylamine zur Antiknitterausrüstung von cellulosehaltigen Textilien
GB2381798A (en) * 2001-11-07 2003-05-14 Christopher Michael Carr Improving resistance to abrasion in garments
GB0225292D0 (en) * 2002-10-30 2002-12-11 Unilever Plc Fabric care composition
CN1878904A (zh) * 2003-11-13 2006-12-13 皇家飞利浦电子股份有限公司 改善织物抗皱性的复合物和方法,容纳这种复合物的装置
MY160707A (en) * 2010-04-01 2017-03-15 Evonik Degussa Gmbh Fabric softener active composition
ITMI20102010A1 (it) * 2010-10-28 2012-04-29 Orlandi Spa Prodotto tessile

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB861693A (en) * 1957-03-04 1961-02-22 Shri Ram Inst For Ind Res Improvements in or relating to the resin treatment of textiles
US2974432A (en) * 1956-02-20 1961-03-14 Koret Of California Press-free crease retained garments and method of manufacture thereof
US4376633A (en) * 1981-06-12 1983-03-15 The United States Of America As Represented By The Secretary Of Agriculture Zwitterion compounds as catalysts in easy-care finishing
EP0363346A2 (fr) * 1988-10-07 1990-04-11 The Procter & Gamble Company Composition détergente liquide pour le linge contenant le composé de silicone avec un amine comme groupe fonctionnel durcissable pour la réduction de la froissabilité
WO1991019037A1 (fr) * 1990-06-06 1991-12-12 The Procter & Gamble Company Gel silicone facilitant le repassage et ameliorant l'esthetique des vetements repasses
WO1996015310A2 (fr) * 1994-11-10 1996-05-23 The Procter & Gamble Company Composition attenuant les faux plis
WO1998004772A1 (fr) * 1996-07-25 1998-02-05 Unilever Plc Composition pour le traitement des tissus
JPH10183472A (ja) * 1996-11-01 1998-07-14 Kao Corp 衣料用仕上げ剤組成物及び衣料の処理方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2974432A (en) * 1956-02-20 1961-03-14 Koret Of California Press-free crease retained garments and method of manufacture thereof
GB861693A (en) * 1957-03-04 1961-02-22 Shri Ram Inst For Ind Res Improvements in or relating to the resin treatment of textiles
US4376633A (en) * 1981-06-12 1983-03-15 The United States Of America As Represented By The Secretary Of Agriculture Zwitterion compounds as catalysts in easy-care finishing
EP0363346A2 (fr) * 1988-10-07 1990-04-11 The Procter & Gamble Company Composition détergente liquide pour le linge contenant le composé de silicone avec un amine comme groupe fonctionnel durcissable pour la réduction de la froissabilité
WO1991019037A1 (fr) * 1990-06-06 1991-12-12 The Procter & Gamble Company Gel silicone facilitant le repassage et ameliorant l'esthetique des vetements repasses
WO1996015310A2 (fr) * 1994-11-10 1996-05-23 The Procter & Gamble Company Composition attenuant les faux plis
WO1998004772A1 (fr) * 1996-07-25 1998-02-05 Unilever Plc Composition pour le traitement des tissus
JPH10183472A (ja) * 1996-11-01 1998-07-14 Kao Corp 衣料用仕上げ剤組成物及び衣料の処理方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 9838, Derwent World Patents Index; Class A14, AN 98-440579, XP002089807 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US6645392B2 (en) 2000-02-14 2003-11-11 The Procter & Gamble Company Method of removing wrinkles from fabric
US6652766B1 (en) 2000-02-14 2003-11-25 The Procter & Gamble Company Articles to aid the ironing of fabrics and methods of use
JP2003525357A (ja) * 2000-02-25 2003-08-26 ビーエーエスエフ アクチェンゲゼルシャフト セルロース−含有織物の防しわ最終仕上げ、および洗濯用後処理剤
US6569823B2 (en) 2000-04-14 2003-05-27 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Fabric care composition
US7429558B2 (en) 2002-01-18 2008-09-30 Unilever Home & Personal Care Division Of Conopco, Inc. Azetidinium modified polymers and fabric treatment composition

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EP0978556A1 (fr) 2000-02-09
DE69826853D1 (de) 2004-11-11
BR9912708A (pt) 2001-05-02
EP0978556B1 (fr) 2004-10-06
CA2338791A1 (fr) 2000-02-17
DE69826853T2 (de) 2005-11-17
AU5332899A (en) 2000-02-28
ATE278758T1 (de) 2004-10-15
JP2002522650A (ja) 2002-07-23

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