EP0540557B1 - Flüssige weichemacher für gewebe mit mikroemulgierten aminosilanen - Google Patents

Flüssige weichemacher für gewebe mit mikroemulgierten aminosilanen Download PDF

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Publication number
EP0540557B1
EP0540557B1 EP91912843A EP91912843A EP0540557B1 EP 0540557 B1 EP0540557 B1 EP 0540557B1 EP 91912843 A EP91912843 A EP 91912843A EP 91912843 A EP91912843 A EP 91912843A EP 0540557 B1 EP0540557 B1 EP 0540557B1
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EP
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Prior art keywords
functional silicone
fabric softener
fabric
silicone
liquid fabric
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Expired - Lifetime
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EP91912843A
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English (en)
French (fr)
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EP0540557A1 (de
Inventor
Timothy Woodrow Coffindaffer
Sheila Gay Buzzee
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Procter and Gamble Co
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Procter and Gamble Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • C11D3/3742—Nitrogen containing silicones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/0017—Multi-phase liquid compositions
    • C11D17/0021—Aqueous microemulsions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/162—Organic compounds containing Si
    • 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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • 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
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • 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
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • This invention relates to fabric care compositions and to a method for treating fabrics in order to improve various properties of the fabric, in particular, reduction of fiber-fiber and yarn-yarn friction.
  • Silicones of this type are typically delivered to textiles in the form of an aqueous emulsion. More recently, much work has concentrated on the aqueous delivery of these systems via microemulsions. The above art suggests that microemulsions have two advantages over conventional "macro" emulsions: (1) they are more stable and (2) they require less mechanical energy to make.
  • EP-A-0,417,047 published on 13.03.91, discloses a stabilised microemulsion comprising an amine functional silicone together with an ampholytic surfactant, wherein the pH of said microemulsion is less than 7.
  • EP-A-0,138,192 discloses stabilised microemulsions of amino functional silicone with an insoluble surfactant. Particularly exemplified is a microemulsion containing an aminofunctional silicone and a quaternary ammonium compound in amount of 1.4%.
  • the shearing instrument in particular the shearing hysteresis measurement, is believed to be indicative of the ease with which fibers and/or yarns move over one another.
  • the shear hysteresis value the better the lubricant.
  • reduced fiber-fiber/yarn-yarn friction (reduced friction between individual fibers within the yarn as well as between the yarn strands) as used herein means that the fabric exhibits a lower shear hysteresis value as measured by the KES shearing instrument. While not wishing to be bound by theory, it is believed that a reduction in reduced fiber-fiber/yarn-yarn friction provides better drape, hand, and wrinkle removal during tumble drying and ironing processes due to the fibers being more easily moved over one another.
  • This invention relates to fabric care compositions comprising a microemulsified amine functional silicone agent and a fabric softener for use in a fabric care operation whereby an effective amount of said microemulsified amine functional silicone is deposited on said fabric for reduced fiber-fiber/yarn-yarn friction.
  • compositions are aqueous fabric softeners. Such compositions are usually added to either the wash or rinse water of a laundering operation. These preferred compositions are aqueous based, water-dispersible compositions which contain from 0.05% to 25%, more preferably from 0.1% to 15% of the microemulsified amine functional silicones. The compositions are diluted in the wash or rinse.
  • the Microemulsified Amine Functional Silicones (MAFS) incorporated into a liquid fabric softener composition of the invention exhibit a synergistic behavior when compared to the corresponding "macro" emulsified material.
  • MAFS performance for reduced fiber-fiber/yarn-yarn friction is not as good as that of the macroemulsified system; however, in the context of a liquid fabric softener composition of the invention the MAFS composition provides a greater reduction in shear hysteresis values than the corresponding macroemulsion in an analogous liquid fabric softener composition.
  • a preferred embodiment comprises: a liquid rinse water composition comprising the microemulsified amine functional silicone plus quaternary ammonium fabric softener.
  • microemulsified amine functional silicone is mixed into a suitable prior art laundry liquid fabric softener composition.
  • the result is a fabric care composition that provides a reduced fiber-fiber/yarn-yarn friction benefit to the treated fabric.
  • silicone microemulsions have been described as translucent silicone emulsions with average particle sizes smaller than 0.14 microns.
  • microemulsions are taught as having two advantages over conventional "macro" emulsions: (1) they are more stable and (2) they require less mechanical energy to make.
  • microemulsions can reduce fiber to fiber and/or yarn to yarn friction as compared to macroemulsions when used with a fabric softener. Since microemulsions are inferior in performance to macroemulsions when used alone, any investigation which starts logically with the individual dispersions would discourage further investigation.
  • the amine functional silicones herein have an average molecular weight of from 1,000 to 100,000, preferably from 1,000 to 50,000, more preferably from 1,500 to 20,000, and can be prepared by emulsion polymerization of low molecular weight polymers and/or monomers, more preferably low molecular weight polymers. Emulsion polymerization can provide a high concentration of microemulsified silicone.
  • the preferred composition of this invention is an aqueous dispersion comprising: a microemulsified amine functional silicone wherein the weight ratio of microemulsified amine functional silicone to fabric softener is from 17:1 to 1:350, preferably from 10:1 to 1:100. Even more preferred weight ratios of microemulsified amine functional silicone to fabric softener are from 1:1 to 1:10, and more preferably, from 1:5 to 1:10. These compositions are added to the rinse water for reduced fiber-fiber/yarn-yarn friction and fabric softening benefits.
  • Suitable fabric softener(s) are selected from the group consisting of:
  • the amount of fabric softener ranges from 2% to 35%, preferably from 4% to 27%, by weight of the total composition.
  • the lower limits are amounts needed to contribute effective fabric softening performance when added to laundry rinse baths in the manner which is customary in home laundry practice.
  • the higher limits are suitable for more concentrated liquid products which require either smaller volume usage or dilution prior to use.
  • microemulsified amine functional silicone in such composition can range from 0.05% to 40%; preferably from 0.1% to 20%; and more preferably from 0.5% to 10% by weight of the concentrate.
  • Suitable fabric softener compounds include quaternary ammonium salts, as well as nonquaternary amines and amine salts.
  • compositions containing cationic nitrogenous compounds in the form of quaternary ammonium salts and substituted imidazolinium salts having two long chain acyclic aliphatic hydrocarbon groups provide fabric softening benefits when used in laundry rinse operations.
  • cationic nitrogenous compounds in the form of quaternary ammonium salts and substituted imidazolinium salts having two long chain acyclic aliphatic hydrocarbon groups provide fabric softening benefits when used in laundry rinse operations.
  • Suitable fabric softening compounds are the nonquaternary amides and the nonquaternary amines.
  • a commonly cited material is the reaction product of higher fatty acids with hydroxy alkyl alkylene diamines.
  • An example of these materials is the reaction product of higher fatty acids and hydroxyethylethylenediamine (See “Condensation Products from beta-hydroxyethylethylenediamine and Fatty Acids or Their Alkyl Esters and Their Application as Textile Softeners in Washing Agents," H.W. Eckert, Fette-Seifen-Anstrichstoff, September 1972, pages 527-533).
  • a particularly preferred fabric softener is in the form of an aqueous dispersion comprising from 3% to 35% by weight of a mixture consisting of:
  • softener compound in general, denotes both singular and plural unless otherwise specified.
  • Preferred carriers are liquids selected from the group consisting of water and mixtures of water and short chain C 1 -C 4 monohydric alcohols.
  • the water which is used can be distilled, deionized, and/or tap water. Mixtures of water and up to 10%, preferably less than 5%, of short chain alcohol such as ethanol, propanol, isopropanol or butanol, and mixtures thereof, are also useful as the carrier liquid. Carriers which are primarily water are desirable.
  • Some short chain alcohols are present in commercially available quaternary ammonium compound products. Such products can be used in the preparation of preferred aqueous compositions of the present invention.
  • the short chain alcohols are normally present in such products at a level of from 0.5% to 10% by weight of the aqueous compositions.
  • Such adjuvants can be added to the compositions herein for their known purposes.
  • Such adjuvants include, but are not limited to, viscosity control agents, perfumes, emulsifiers, preservatives, antioxidants, bactericides, fungicides, colorants, dyes, fluorescent dyes, brighteners, opacifiers, freeze-thaw control agents, soil release agents, and shrinkage control agents, and other agents to provide ease of ironing (e.g., starches).
  • These adjuvants, if used, are added at their usual levels, generally each of up to 5% by weight of the preferred liquid composition.
  • Viscosity control agents can be organic or inorganic in nature.
  • organic viscosity modifiers are fatty acids and esters, fatty alcohols, and water-miscible solvents such as short chain alcohols.
  • inorganic viscosity control agents are water-soluble ionizable salts.
  • 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. Calcium chloride is preferred.
  • the ionizable salts are particularly useful during the process of mixing the ingredients to make the liquid compositions herein, and later to obtain the desired viscosity.
  • the amount of ionizable salts used depends on the amount of active ingredients used in such compositions and can be adjusted according to the desires of the formulator. Typical levels of salts used to control the composition viscosity are from 20 to 6,000 parts per million (ppm), preferably from 20 to 4,000 ppm by weight of the composition.
  • Soil release agents are desirable additives at levels of from 0.1% to 5%.
  • Suitable soil release agents are disclosed in U.S. Pat. Nos. 4,702,857, Gosselink, issued Oct. 27, 1987; 4,711,730, Gosselink and Diehl, issued Dec. 8, 1987; 4,713,194, Gosselink issued Dec. 15, 1987; and mixtures thereof.
  • Other soil release polymers are disclosed in U.S. Pat. Nos.: 4,749,596, Evans, Huntington, Stewart, Wolf, and Zimmerer, issued June 7, 1988; 3,928,213, Temple, Heuring, and Prentice, issued Dec. 23, 1975; 4,136,038, Pracht and Burns, issued Jan. 23, 1979; and 4,661,267, Dekker, Konig, Straathof, and Gosselink, issued Apr. 28, 1987.
  • Typical levels of compatible bactericides used in the present compositions are from 1 to 1,500 ppm by weight of the composition.
  • antioxidants examples include propyl gallate, available from Eastman Chemical Products, Inc., under the trade names Tenox® PG and Tenox S-1, and butylated hydroxy toluene, available from UOP Process Division under the trade name Sustane® BHT.
  • compositions can contain other silicone fluids to provide additional benefits such as improved fabric feel.
  • the preferred adjunct silicones are polydimethylsiloxanes of viscosity of from 100 centistokes (cs) to 100,000 cs, preferably from 200 cs to 60,000 cs. These adjunct silicones can be used as is, or can be conveniently added to the softener compositions in a preemulsified form which is obtainable directly from suppliers.
  • silicones examples include 60% emulsion of polydimethylsiloxane (350 cs) sold by Dow Corning Corporation under the trade name DOW CORNING® 1157 Fluid and 50% emulsion of polydimethylsiloxane (10,000 cs) sold by General Electric Company under the trade name General Electric® SM 2140 Silicones.
  • the optional silicone component can be used in an amount of from 0.1% to 6% by weight of the composition.
  • a preferred composition contains from 1 ppm to 1,000 ppm of bactericide, from 0.2% to 2% of perfume, from 0% to 3% of polydimethylsiloxane, from 0% to 0.4% of calcium chloride, from 10 ppm to 100 ppm of dye, and from 0% to 10% of short chain alcohols, by weight of the total composition.
  • the pH of the preferred compositions of this invention is generally adjusted to be in the range of from 2 to 11, preferably from 2 to 8. Adjustment of pH is normally carried out by including a small quantity of free acid or free base in the formulation. Any acidic material can be used; its selection can be made by anyone skilled in the softener arts on the basis of cost, availability, or safety. Any suitable acid can be used to adjust pH. Preferred are hydrochloric, sulfuric, phosphoric and formic acid. Similarly, any suitable base, e.g., sodium hydroxide, can also be used to adjust pH. For the purposes of this invention, pH is measured by a glass electrode in full strength softening composition in comparison with a standard calomel reference electrode.
  • compositions of the present invention can be prepared by a number of methods. Some convenient and satisfactory methods are disclosed in the following nonlimiting examples.
  • a liquid fabric softener composition containing a micro emulsified amine curable silicone is prepared in the following manner. About 4.33 parts di(hydrogenated tallow)dimethylammonium chloride (DTDMAC), about 1.00 part methyl-1-tallow amidoethyl-2-tallowimidazolinium methylsulfate and about 0.025 parts of a 1% dye solution are weighed into a premix vessel.
  • DTDMAC di(hydrogenated tallow)dimethylammonium chloride
  • a 1% dye solution are weighed into a premix vessel.
  • the premix is added, with agitation, to a mix vessel (44°C) containing about 88.14 parts distilled water and about 0.025 parts antioxidant solution. Then about 0.45 parts of perfume is added to this "main" mix. The main mix is then cooled to about 21°C, to which is added, with stirring, about 7.15 parts amine functional silicone microemulsion (about 14% silicone).
  • a microemulsified amine functional silicone and fabric softener composition is prepared using Procedure A.
  • the approximate levels of the ingredients are: 2.00 parts Mazamide 6, 0.80 parts MTTMAC, 4.03 parts DTDMAC (defined hereinbefore), 1.00 parts of the imidazolinium salt in Example I, 0.42 parts perfume, 1.28 parts alcohol (from actives), 10.00 parts 14% microemulsified amine functional silicone, and the balance is distilled water. See Table 2 and Example I for a recap of the ingredients and method of preparation.
  • a microemulsified amine functional silicone and fabric softener composition is prepared using Procedure A.
  • the approximate levels of ingredients are: 17.50 parts Mazamide 6, 6.50 parts DTDMAC, 1.32 parts perfume, 2.07 parts alcohol (from actives), 12.00 parts 14% micro emulsified amine functional silicone, and the balance is distilled water. See Table 2 and Example I for a recap of the ingredients and method of preparation.
  • a microemulsified amine functional silicone and fabric softener composition is prepared using Procedure A.
  • the approximate levels of ingredients are: 3.75 parts DTDMAC, 3.40 parts imidazoline, 0.57 parts MTTMAC, 0.40 parts perfume, 0.025 parts dye, 0.77 parts alcohol (from actives), 0.4-0.9 parts HCl, 7.15 parts MAFS (14%) and the balance is distilled water.
  • This composition contains about 1% amine functional silicone fluid.
  • a fabric softener composition is prepared as in Product C, except that about 3.03 parts amine functional silicone macroemulsion (33% silicone) is added. This composition contains about 1% amine functional silicone fluid.
  • Products C & D are used as rinse-added fabric softeners to treat poly cotton (65%/35%) fabrics.
  • the fabrics are treated via one wash/rinse/dry treatment.
  • the detergents used are TIDE® and LIQUID TIDE®.
  • microemulsified amine functional silicone delivered via a liquid fabric softener matrix shows improved reduction in shear hysteresis on poly-cotton fabric relative to the traditional macroemulsion delivered via a liquid fabric softener matrix.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (8)

  1. Flüssige gewebeweichmachende Zusammensetzung, umfassend:
    a) ein mikroemulgiertes aminofunktionelles Silikon mit einem mittleren Molekulargewicht von 1.000 bis zu 1.000.000,
    b) eine Gewebeweichmacherverbindung, welche unter quaternären Ammoniumverbindungen, Fettaminverbindunqen, Fettamidverbindungen, Fettsäureverbindungen, Fettalkoholverbindungen und Gemischen hievon ausgewählt ist,
    c) ein geeignetes Trägermaterial für a) und b), und
    wobei das genannte mikroemulgierte aminofunktionelle Silikon durch Emulsionspolymerisation von einem Polymer mit niedrigerem Molekulargewicht erhalten wird, welches Polymer unter Silikonpolymeren, Silikonmonomeren und Gemischen hievon ausgewählt ist, und wobei die genannte Gewebeweichmacherverbindung in einer Menge von 2 Gew.-% bis 35 Gew.-% der Zusammensetzung vorliegt.
  2. Flüssige gewebeweichmachende Zusammensetzung nach Anspruch 1, wobei das genannte mikroemulgierte aminofunktionelle Silikon in einer Menge von 0,05 Gew.-% bis 25 Gew.-%, vorzugsweise von 0,1 Gew.-% bis 15 Gew.-% und stärker bevorzugt von 0,5 Gew.-% bis 10 Gew.-% der Zusammensetzung vorliegt.
  3. Flüssige gewebeweichmachende Zusammensetzung nach einem der Ansprüche 1 oder 2, wobei das Gewichtsverhältnis von dem genannten mikroemulgierten aminofunktionellen Silikon zu dem genannten Gewebeweichmacher von 10:1 bis 1:100, vorzugsweise von 1:1 bis 1:10, stärker bevorzugt von 1:5 bis 1:10 reicht.
  4. Flüssige gewebeweichmachende Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei der genannte Gewebeweichmacher eine quaternäre Ammoniumverbindung ist.
  5. Flüssige gewebeweichmachende Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei der genannte Gewebeweichmacher ein Gemisch aus quaternären Ammoniumverbindungen, Fettaminverbindungen und Fettamidverbindungen ist.
  6. Flüssige gewebeweichmachende Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei der genannte Gewebeweichmacher eine Fettaminverbindung ist.
  7. Flüssige gewebeweichmachende Zusammensetzung nach einem der Ansprüche 1 bis 6, wobei der genannte Gewebeweichmacher in einer Menge von 4 Gew.-% bis 27 Gew.-% der Zusammensetzung vorliegt.
  8. Verfahren zur Verringerung der Faser-Faser/Garn-Garn-Reibung in behandelten Geweben, umfassend das In-Kontakt-Bringen der genannten Gewebe mit einer mit Wasser verdünnten wirksamen Menge einer flüssigen gewebeweichmachenden Zusammensetzung, wie sie in einem der Ansprüche 1 bis 7 beansprucht ist.
EP91912843A 1990-07-23 1991-07-08 Flüssige weichemacher für gewebe mit mikroemulgierten aminosilanen Expired - Lifetime EP0540557B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US55743890A 1990-07-23 1990-07-23
US557438 1990-07-23
PCT/US1991/004729 WO1992001773A1 (en) 1990-07-23 1991-07-08 Liquid fabric softeners containing microemulsified amino silanes

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EP0540557A1 EP0540557A1 (de) 1993-05-12
EP0540557B1 true EP0540557B1 (de) 1996-10-16

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EP (1) EP0540557B1 (de)
JP (1) JPH05508889A (de)
CN (1) CN1050162C (de)
AU (1) AU8199791A (de)
CA (1) CA2087985C (de)
HU (1) HUT63455A (de)
MX (1) MX9100324A (de)
MY (1) MY106826A (de)
NZ (1) NZ239069A (de)
PL (1) PL297655A1 (de)
SK (1) SK280339B6 (de)
WO (1) WO1992001773A1 (de)

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RU2014111460A (ru) 2011-08-26 2015-10-10 Колгейт-Палмолив Компани Композиция для уменьшения сминаемости ткани
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SK2993A3 (en) 1993-09-09
AU8199791A (en) 1992-02-18
CN1060125A (zh) 1992-04-08
MX9100324A (es) 1992-02-28
CA2087985A1 (en) 1992-01-24
PL297655A1 (de) 1992-07-13
CA2087985C (en) 1997-04-15
WO1992001773A1 (en) 1992-02-06
HU9300189D0 (en) 1993-04-28
CN1050162C (zh) 2000-03-08
EP0540557A1 (de) 1993-05-12
NZ239069A (en) 1994-06-27
JPH05508889A (ja) 1993-12-09
MY106826A (en) 1995-07-31
SK280339B6 (sk) 1999-12-10
HUT63455A (en) 1993-08-30

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