EP0491531A1 - Detergent compositions - Google Patents

Detergent compositions Download PDF

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Publication number
EP0491531A1
EP0491531A1 EP19910311635 EP91311635A EP0491531A1 EP 0491531 A1 EP0491531 A1 EP 0491531A1 EP 19910311635 EP19910311635 EP 19910311635 EP 91311635 A EP91311635 A EP 91311635A EP 0491531 A1 EP0491531 A1 EP 0491531A1
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EP
European Patent Office
Prior art keywords
amount
composition according
weight
primary alkyl
diol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19910311635
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German (de)
English (en)
French (fr)
Inventor
Mohamad Sami Unilever Research Port Falou
Anthony David Unilever Research Port Gough
Michael Unilever Research Port Hull
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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Publication of EP0491531A1 publication Critical patent/EP0491531A1/en
Withdrawn legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/83Mixtures of non-ionic with anionic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/825Mixtures of compounds all of which are non-ionic
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2041Dihydric alcohols
    • C11D3/2044Dihydric alcohols linear
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146Sulfuric acid esters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/662Carbohydrates or derivatives
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2006Monohydric alcohols
    • C11D3/2024Monohydric alcohols cyclic; polycyclic

Definitions

  • This invention relates to a detergent composition, especially but not exclusively, to built compositions suitable for the washing of fabrics.
  • Fabric washing compositions traditionally contain one or more detergent active materials in addition to various other ingredients such as detergency builders, bleaches, fluorescers, perfumes etc. Notable applications of detergent compositions are to clean fabrics, usually by washing portable fabric items in a bowl or in a washing machine, to clean crockery and cooking utensils, again by washing in a bowl (hand dishwashing), and to clean hard surfaces such as glass, glazed surfaces, plastics, metals and enamels.
  • a number of different detergent active materials have been proposed in the art.
  • the present invention provides a built detergent composition for washing fabrics containing 2 to 50% by weight of a surfactant mixture which comprises
  • the diol and the other surfactant(s) generally give a synergistic enhancement of oily soil removal, giving greater removal of oily soil than is found with compositions of the same surfactants which are somewhat similar but outside the specified ranges.
  • composition in accordance with the invention which is rich in primary alkyl sulphate, contains some diol and possibly a small quantity of ethoxylated alcohol may possess better oily soil detergency than either primary alkyl sulphate or the diol alone yet not be as good as the ethoxylated alcohol alone.
  • compositions which is rich in primary alkyl sulphate may be preferred over the ethoxylated alcohol for other reasons, such as ability to formulate a solid product, ability to generate foam or effectiveness against other soils.
  • compositions of this invention will now be considered by turn.
  • hydrocarbyl group R in the general formula will generally be alkyl or alkenyl of 8 to 16 carbon atoms, preferably 8 to 12.
  • 1,2-Alkane diols are known compounds and can be prepared by standard methods for the preparation of diols. They can be manufactured from terminal olefins by epoxidation and then hydrolysis.
  • group R examples include cycloaliphatic groups and aromatic-aliphatic groups such as phenylethyl or dimethyl phenyl.
  • Possible primary alkyl sulphates (a), also known as sulphated fatty alcohol salts, include those of mixed alkyl chain length, in which the ratio of C12 alkyl chains to C18 alkyl chains is in the range of from 9:4 to 1:6.
  • a suitable material can be obtained from a mixture of synthetic lauryl and oleyl alcohols in appropriate proportions.
  • the solubilizing cation of the alkyl sulphates is preferably an alkali metal, notably sodium or potassium.
  • nonionic surfactant (b) is ethoxylated nonionic surfactants for which the average number of ethylene oxide residues is high enough to yield an HLB value of at least 11.0.
  • these may in particular be ethoxylated alcohols. In such compounds the alcohol generally contains from 9 to 15 carbon atoms.
  • alkyl polyglycosides of general formula R2O(R3O) t (G) x provided the value of x is sufficiently high to give an HLB of at least 11.
  • the hydrophobic group R3 is preferably aliphatic, either saturated or unsaturated, notably straight or branched alkyl, alkenyl, hydroxyalkyl or hydroxyalkenyl.
  • R3 may include an aryl group for example alkyl-aryl, alkenyl-aryl and hydroxyalkyl-aryl.
  • R is alkyl or alkenyl of 8 to 16 carbon atoms.
  • t in the general formula above is preferably zero, so that the -(RO) t - unit of the general formula is absent. In that case the general formula becomes RO(G) x
  • R3O is an ethylene oxide residue.
  • Other likely possibilities are propylene oxide and glycerol residues.
  • the value of t (which may be an average value) will preferably lie in the range from 0.5 to 3.
  • the group G is typically derived from fructose, glucose, mannose, galactose, talose, gulose, allose, altrose, idose, arabinose, xylose, lyxose and/or ribose.
  • the G is provided substantially exclusively by glucose units.
  • x which is an average, is usually termed the degree of polymerization. Desirably x varies between 1 and 8. Values of x may lie between 1 and 3, especially 1 and 1.8.
  • Polyglycosides of particular interest have x in the narrow range from 1 or 1.2 up to 1.4 or especially 1.3. If x exceeds 1.3 it preferably lies in the range 1.3 or 1.4 to 1.8.
  • R is C8 to C14 alkyl or alkenyl.
  • the surfactant mixture may be diol (i) with primary alkyl sulphate (a) diol (i) with nonionic surfactant (b) diol (i) with both of (a) and (b).
  • the amounts of (a) and (b) must comply with certain limits which require, in qualitative terms a mixture in which (a) or (b) is preponderant over the other, or a mixture in which the amounts of (a) and (b) are not too far from being equal.
  • This latter possibility is a range of 40:60 to 70:30.
  • nonionic surfactant (b) may, for example, be an ethoxylated nonionic or an alkylpolyglycoside (each as specified above) or a mixture of the two.
  • Detergent compositions of the invention may contain yet further surfactants, outside the definitions specified for (i) and (ii).
  • the proviso stated above limits the amount of non-soap anionic surfactant other than primary alkyl sulphate.
  • additional surfactants is not preferred, since it may harm the desired synergy. Consequently, the amount of any surfactants other than (i) and (ii) as defined is likely to be less than 50% by weight better less than 25% or even 10%, of the surfactant mixture.
  • Additional surfactant may be anionic, nonionic or amphoteric. Cationic surfactant is possible, especially if anionic surfactant is absent but is preferably excluded.
  • Detergent compositions of the invention also contain detergency builder. Generally the amount of detergency builder is from 7 to 70% by weight of the composition.
  • a detergent composition of this invention is in solid form, the composition is likely to contain at least 10 or 15% of builder.
  • compositions according to the invention be approximately neutral or preferably alkaline, that is when the composition is dissolved in an amount to give surfactant concentration of 1 g/l in distilled water at 25°C the pH should desirably be at least 7.5.
  • the pH will usually be greater, such as at least 9.
  • the compositions may include a water-soluble alkaline salt. This salt may be a detergency builder (as described in more detail below) or a non-building alkaline material.
  • compositions of the invention contain a detergency builder material
  • this may be any material capable of reducing the level of free calcium ions in the wash liquor and will preferably provide the compositions with other beneficial properties such as the generation of an alkaline pH and the suspension of soil removed from the fabric.
  • Examples of phosphorus-containing inorganic detergency builders when present, include the water-soluble salts, especially alkali metal pyrophosphates, orthophosphates, polyphosphates and phosphonates.
  • Specific examples of inorganic phosphate builders include sodium and potassium tripolyphosphates, orthophosphates and hexametaphosphates.
  • non-phosphorus-containing inorganic detergency builders when present, include water-soluble alkali metal carbonates, bicarbonates, silicates and crystalline and amorphous alumino silicates. Specific examples include sodium carbonate (with or without calcite seeds), potassium carbonate (with or without calcite seeds), sodium and potassium bicarbonates and silicates.
  • organic detergency builders when present include the alkali metal, ammonium and substituted ammonium polyacetates, carboxylates, polycarboxylates, polyacetyl carboxylates and polyhydroxsulphonates. Specific examples include sodium, potassium, lithium, ammonium and substituted ammonium salts of ethylenediaminetetraacetic acid, nitrilotriacetic acid, oxydisuccinic acid, melitic acid, benzene polycarboxylic acids and citric acid. Further possibilities are tartrate monosuccinates, tartrate disuccinates, dipicolinic acid, cheledamic acid, carboxy methyloxysuccinate and hydroxyethyliminodiacetic acid.
  • ingredients already mentioned a number of optional ingredients may also be present.
  • other ingredients which may be present in the composition are polymers containing carboxylic or sulphonic acid groups in acid form or wholly or partially neutralised to sodium or potassium salts, the sodium salts being preferred.
  • Preferred polymers are homopolymers and copolymers of acrylic acid and/or maleic acid or maleic anhydride.
  • the molecular weights of homopolymers and copolymers are generally 1000 to 150,000, preferably 1500 to 100,000.
  • the amount of any polymer may lie in the range from 0.5 to 5% by weight of the composition.
  • Other suitable polymeric materials are cellulose ethers such as carboxy methyl cellulose, methyl cellulose, hydroxy alkyl celluloses, and mixed ethers, such as methyl hydroxy ethyl cellulose, methyl hydroxy propyl cellulose, and methyl carboxy methyl cellulose. Mixtures of different cellulose ethers, particularly mixtures of carboxy methyl cellulose and methyl cellulose, are suitable.
  • Polyethylene glycol of molecular weight from 400 to 50,000, preferably from 1000 to 10,000, and copolymers of polyethylene oxide with polypropylene oxide are suitable as also are copolymers of polyacrylate with polyethylene glycol.
  • Polyvinyl pyrrolidone of molecular weight of 10,000 to 60,000 preferably of 30,000 to 50,000 and copolymers of polyvinyl pyrrolidone with other poly pyrrolidones are suitable.
  • Polyacrylic phosphinates and related copolymers of molecular weight 1000 to 100,000, in particular 3000 to 30,000 are also suitable.
  • ingredients which may be present in the composition include fabric softening agents such as fatty amines, fabric softening clay materials, lather boosters such as alkanolamides, particularly the monoethanolamides derived from palm kernel fatty acids and coconut fatty acids, lather depressants, oxygen-releasing bleaching agents such as sodium perborate and sodium percarbonate, typically accompanied by peracid bleach precursors, organic peracids, chlorine-releasing bleaching agents such as trichloroisocyanuric acid, inorganic salts such as sodium sulphate, and, usually present in very minor amounts, fluorescent agents, perfumes including deodorant perfumes, enzymes such as cellulases, proteases, lipases and amylases, germicides and colourants.
  • fabric softening agents such as fatty amines, fabric softening clay materials
  • lather boosters such as alkanolamides, particularly the monoethanolamides derived from palm kernel fatty acids and coconut fatty acids
  • lather depressants oxygen-
  • the detergent compositions according to the invention may be in any suitable form including powders, bars, liquids and pastes.
  • suitable liquid compositions may be non-aqueous or aqueous, the latter being either isotropic or lamellar structured.
  • the compositions may be prepared by a number of different methods according to their physical form. In the case of granular products they may be prepared by dry-mixing, coagglomeration, spray-drying from an aqueous slurry or any combination of these methods.
  • One preferred physical form is a granule incorporating a detergency builder salt. This may be prepared by conventional granulation techniques or spray drying.
  • Another preferred physical form is a lamellar structured aqueous liquid, for heavy duty fabrics washing, in which the surfactant mixture provides structure capable of suspending particulate solids.
  • the surfactant (ii) may be nonionic surfactant (b).
  • the aqueous continuous phase of such a liquid will usually contain dissolved electrolyte. Electrolyte may be dissolved only in the aqueous continuous phase or may also be present as suspended solid particles. Particles of solid materials which are insoluble in the aqueous phase may be suspended alternatively or in addition to any solid electrolyte particles.
  • the suspended solid can comprise suspended solids which are substantially the same as the dissolved electrolyte, being an excess of same beyond the solubility limit. This solid is usually present as a detergency builder, i.e. to counteract the effects of calcium ion water hardness in the wash.
  • the suspended solid usually comprises a particulate abrasive, insoluble in the system. In that case the electrolyte, present to contribute to the structuring of the active material in the dispersed phase, is generally different from the abrasive compounds. In certain cases, the abrasive can however comprise partially soluble salts which dissolve when the product is diluted.
  • the structure is usually used for thickening the product to give consumer-preferred flow properties, and sometimes to suspend pigment particles.
  • Figures 1 and 2 are triangular plots of results from Examples 3 and 7.
  • compositions were prepared having as a general formulation:
  • Sokolan CP5 is an acrylic/maleic copolymer available from BASF.
  • the detergent active was provided by various proportions of Dodecane 1,2-diol available from Aldrich Chemical Co. and Synperonic A7 available from I.C.I.
  • Synperonic A7 is a C13-C15 alcohol ethoxylated with an average of seven ethylene oxide residues. It has an HLB of 11.7.
  • compositions were added to 24°FH water at a concentration of 6g/litre.
  • the resulting wash liquors had a pH of 10 and were used to wash polyester test cloths soiled with radiolabelled triolein. Washing was carried out at 40°C for 20 minutes in a Tergotometer.
  • compositions were prepared having as a general formulation:
  • the detergent active was provided by mixtures of various 1,2-diols and primary alkyl sulphate (PAS) with an alkyl chain length of 14 and 15 carbon atoms.
  • the alkane 1,2-diols ranged from C8 to C16 chain length.
  • compositions were added to 24°FH water at a concentration of 6g/litre giving wash liquors with a pH of 10. These were used to wash polyester test cloths soiled with radiolabelled triolein, as in the preceding example. Results were as follows:
  • Example 2 The procedure of Example 2 was repeated using as detergent active various mixtures of C12 1,2-diol, primary alkyl sulphate with a chain length of 14 and 15 carbon atoms and Synperonic A7 as used in Example 1.
  • the results (% triolein removal) are given in a table below.
  • the amounts of the individual surfactants are given as percentages of the total quantity of all three surfactants, which was 13% of the composition.
  • Aqueous wash liquors were prepared containing the following materials in deionized water.
  • the alkylpolyglycoside was APG 300 from Horizon Chemical Co. This was of the formula RO(G) x where R is a 9 to 11 carbon alkyl chain, G is glucose and x has an average value of 1.4. It had an HLB value of approximately 11 to 12.
  • the dodecane 1,2-diol is available from Aldrich Chemical Co.
  • Wash liquors were prepared with various ratios of the two surfactants and used to wash polyester test cloths soiled with radiolabelled triolein. Washing was carried out at 40°C for 20 minutes in a Tergotometer.
  • Example 4 was repeated using a different alkylpolyglycoside.
  • APG 500 from Horizon was used. This has the formula RO(G) x where R is C12 and C13 alkyl, G is glucose and x is 1.4. It had an HLB value of approximately 11.5 to 12.5. Results were:
  • Example 1 The procedure of Example 1 was repeated using as detergent active various proportions of an alkylpolyglycoside and Dodecane 1,2-diol.
  • the alkylpolyglycoside was APG 550 from Horizon. This is of the general formula RO(G) x where R is a 12 and 13 carbon atom alkyl chain, G is glucose and x has an average value of 1.8. It had an HLB value of approximately 12 to 13.
  • compositions were added to 24°FH water at a concentration of 6g/litre.
  • the resulting wash liquors had a pH of 10 and were used to wash polyester test cloths as in previous Examples.
  • the cloths came from a different batch; consequently these figures cannot be compared directly with the results from Example 1. Results were:
  • the previous Example 6 was repeated, using various mixtures of Synperonic A7 and APG 550 as the nonionic surfactant.
  • the results, including these of the previous Example are given in the following table in which the amounts of APG 550, Dodecane 1,2-diol and Synperonic A7 are expressed as percentages of the total quantity of all three (which was a constant 13% of the overall composition).
  • the results are also plotted as a triangular diagram which appears as Fig. 2.
  • compositions were prepared having as a general formulation:
  • the detergent active was provided by various proportions of alkylpolyglycoside, and dodecane 1,2-diol and coconut alkyl sulphate (PAS).
  • the alkylpolyglycoside was APG 600 from Horizon (also available as Plantaren APG 600 from Henkel). This is of the general formula RO(G) x where R is a coconut alkyl chain (i.e. principally C12 and C14), G is glucose and x has an average value of 1.4. It has an HLB value of approximately 12.
  • compositions were added to 24° FH water at a concentration of 5 g/litre and used to wash polyester test cloths by the procedure as in Examples 1 and 2.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
EP19910311635 1990-12-18 1991-12-13 Detergent compositions Withdrawn EP0491531A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9027416 1990-12-18
GB909027416A GB9027416D0 (en) 1990-12-18 1990-12-18 Detergent composition

Publications (1)

Publication Number Publication Date
EP0491531A1 true EP0491531A1 (en) 1992-06-24

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EP19910311635 Withdrawn EP0491531A1 (en) 1990-12-18 1991-12-13 Detergent compositions

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EP (1) EP0491531A1 (ja)
JP (1) JPH04300998A (ja)
BR (1) BR9105472A (ja)
CA (1) CA2057462A1 (ja)
GB (1) GB9027416D0 (ja)
ZA (1) ZA919952B (ja)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0593406A1 (en) * 1992-10-13 1994-04-20 The Procter & Gamble Company Non-aqueous liquid detergent compositions
US5547476A (en) * 1995-03-30 1996-08-20 The Procter & Gamble Company Dry cleaning process
US5575864A (en) * 1994-03-23 1996-11-19 Haley; Kalliopi S. Method for cleaning a hard surface with an all-purpose liquid cleaning composition
US5591236A (en) 1995-03-30 1997-01-07 The Procter & Gamble Company Polyacrylate emulsified water/solvent fabric cleaning compositions and methods of using same
US5630847A (en) * 1995-03-30 1997-05-20 The Procter & Gamble Company Perfumable dry cleaning and spot removal process
US5630848A (en) * 1995-05-25 1997-05-20 The Procter & Gamble Company Dry cleaning process with hydroentangled carrier substrate
US5632780A (en) * 1995-03-30 1997-05-27 The Procter & Gamble Company Dry cleaning and spot removal proces
EP0687290B1 (de) * 1993-03-05 1997-09-17 Henkel Kommanditgesellschaft auf Aktien Fussbodenreinigungsmittel
EP0805200A1 (en) * 1996-05-03 1997-11-05 The Procter & Gamble Company Hard surface cleaning compositions
US5687591A (en) 1995-06-20 1997-11-18 The Procter & Gamble Company Spherical or polyhedral dry cleaning articles
WO1998016611A1 (en) * 1996-10-11 1998-04-23 The Procter & Gamble Company Laundry bar compositions comprising dihydric alcohol
US5804548A (en) 1995-03-30 1998-09-08 The Procter & Gamble Company Dry cleaning process and kit
US5912408A (en) 1995-06-20 1999-06-15 The Procter & Gamble Company Dry cleaning with enzymes
EP1092804A1 (de) * 1999-10-16 2001-04-18 Ciba Spezialitätenchemie Pfersee GmbH Zusammensetzung für die Vorbehandlung von Fasermaterialien

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4629354B2 (ja) * 2004-02-25 2011-02-09 三洋化成工業株式会社 界面活性剤組成物

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US2679482A (en) * 1949-10-08 1954-05-25 Colgate Palmolive Co Synthetic detergent compositions
US3705113A (en) * 1968-10-24 1972-12-05 Chevron Res Hydrogenated olefin sulfonate-alkyl-1,2-glycol detergent compositions
US3766062A (en) * 1971-08-03 1973-10-16 Colgate Palmolive Co 1,2-alkanediol containing fabric softening compositions
WO1990009427A1 (de) * 1989-02-16 1990-08-23 Henkel Kommanditgesellschaft Auf Aktien Waschmittel mit waschkraftverstärker

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US4692277A (en) * 1985-12-20 1987-09-08 The Procter & Gamble Company Higher molecular weight diols for improved liquid cleaners
JPH0759716B2 (ja) * 1986-08-29 1995-06-28 ライオン株式会社 皮膚刺激を抑制した界面活性剤組成物
JP2571117B2 (ja) * 1989-02-03 1997-01-16 花王株式会社 洗浄剤組成物

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US2679482A (en) * 1949-10-08 1954-05-25 Colgate Palmolive Co Synthetic detergent compositions
US3705113A (en) * 1968-10-24 1972-12-05 Chevron Res Hydrogenated olefin sulfonate-alkyl-1,2-glycol detergent compositions
US3766062A (en) * 1971-08-03 1973-10-16 Colgate Palmolive Co 1,2-alkanediol containing fabric softening compositions
WO1990009427A1 (de) * 1989-02-16 1990-08-23 Henkel Kommanditgesellschaft Auf Aktien Waschmittel mit waschkraftverstärker

Non-Patent Citations (1)

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Title
CHEMICAL ABSTRACTS, vol. 114, no. 4, 28 January 1991, Columbus, Ohio, US; abstract no. 26224, *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0593406A1 (en) * 1992-10-13 1994-04-20 The Procter & Gamble Company Non-aqueous liquid detergent compositions
EP0687290B1 (de) * 1993-03-05 1997-09-17 Henkel Kommanditgesellschaft auf Aktien Fussbodenreinigungsmittel
US5837065A (en) * 1994-03-23 1998-11-17 Amway Corporation Concentrated all-purpose light duty liquid cleaning composition and method of use
US5575864A (en) * 1994-03-23 1996-11-19 Haley; Kalliopi S. Method for cleaning a hard surface with an all-purpose liquid cleaning composition
US5630847A (en) * 1995-03-30 1997-05-20 The Procter & Gamble Company Perfumable dry cleaning and spot removal process
US5632780A (en) * 1995-03-30 1997-05-27 The Procter & Gamble Company Dry cleaning and spot removal proces
US5591236A (en) 1995-03-30 1997-01-07 The Procter & Gamble Company Polyacrylate emulsified water/solvent fabric cleaning compositions and methods of using same
US5804548A (en) 1995-03-30 1998-09-08 The Procter & Gamble Company Dry cleaning process and kit
US5547476A (en) * 1995-03-30 1996-08-20 The Procter & Gamble Company Dry cleaning process
US5630848A (en) * 1995-05-25 1997-05-20 The Procter & Gamble Company Dry cleaning process with hydroentangled carrier substrate
US5687591A (en) 1995-06-20 1997-11-18 The Procter & Gamble Company Spherical or polyhedral dry cleaning articles
US5912408A (en) 1995-06-20 1999-06-15 The Procter & Gamble Company Dry cleaning with enzymes
EP0805200A1 (en) * 1996-05-03 1997-11-05 The Procter & Gamble Company Hard surface cleaning compositions
WO1998016611A1 (en) * 1996-10-11 1998-04-23 The Procter & Gamble Company Laundry bar compositions comprising dihydric alcohol
EP1092804A1 (de) * 1999-10-16 2001-04-18 Ciba Spezialitätenchemie Pfersee GmbH Zusammensetzung für die Vorbehandlung von Fasermaterialien
US6802871B1 (en) 1999-10-16 2004-10-12 Ciba Specialty Chemicals Corporation Composition for pretreating fiber materials

Also Published As

Publication number Publication date
ZA919952B (en) 1993-06-18
BR9105472A (pt) 1992-09-01
JPH04300998A (ja) 1992-10-23
CA2057462A1 (en) 1992-06-19
GB9027416D0 (en) 1991-02-06

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