EP0088520A2 - Composition d'adoucissage pour matières textiles - Google Patents

Composition d'adoucissage pour matières textiles Download PDF

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Publication number
EP0088520A2
EP0088520A2 EP83300625A EP83300625A EP0088520A2 EP 0088520 A2 EP0088520 A2 EP 0088520A2 EP 83300625 A EP83300625 A EP 83300625A EP 83300625 A EP83300625 A EP 83300625A EP 0088520 A2 EP0088520 A2 EP 0088520A2
Authority
EP
European Patent Office
Prior art keywords
lanolin
fabric softening
composition
cationic
weight
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.)
Granted
Application number
EP83300625A
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German (de)
English (en)
Other versions
EP0088520A3 (en
EP0088520B1 (fr
Inventor
Michael William Parslow
Edwin Willis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever NV
Original Assignee
Unilever NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by Unilever NV filed Critical Unilever NV
Priority to AT83300625T priority Critical patent/ATE42570T1/de
Publication of EP0088520A2 publication Critical patent/EP0088520A2/fr
Publication of EP0088520A3 publication Critical patent/EP0088520A3/en
Application granted granted Critical
Publication of EP0088520B1 publication Critical patent/EP0088520B1/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
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/384—Animal products
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates

Definitions

  • the present invention relates to a fabric softening composition.
  • a fabric softening composition In particular, but not exclusively, it relates to an aqueous based concentrated fabric softening composition.
  • fabric softening agents are applied from an aqueous liquor which is made up by adding a relatively small volume of a fabric softening composition to a large volume of water, for example during the rinse cycle in an automatic washing machine.
  • the fabric softening composition is usually an aqueous liquid product containing less than about 8% of a cationic fabric softening agent.
  • the product For a number of reasons, including for example the cost of packaging, it would be preferred if the product were to contain more than 8% of the active ingredient but due to difficulties in manufacture, storage and ease of use of the products, it has only been possible to do this in the past with some difficulty.
  • the present invention seeks to overcome one or more of the objectives referred to above by the combined use of a cationic fabric softening agent and lanolin or a lanolin-like material.
  • a fabric softening composition comprising an aqueous base and at least 0.5% by weight of a cationic fabric softening agent, characterised in that it further comprises from 0.25% up to 10% by weight of lanolin or-a lanolin-like material.
  • An essential component of the present invention is lanolin or a lanolin-like material.
  • Lanolin is wool wax which has been purified by various purification steps including washing, neutralisation, filtration, bleaching and deodorisation.
  • Lanolin is composed primarily of esters which constitute the active constituents in the present invention and which yield on hydrolysis a mixture of complex alcohols and fatty acids.
  • the alcohols which form about half of the ester component by weight, include sterols and terpene alcohols.
  • the sterols amount to about 30% and include cholesterol, 7-dehydrocholesterol and cerebosterol and dihydrocholesterol (cholestanol).
  • the terpene alcohols include lanesterol (C 30 N 50 O), dihydrolanesterol (C 30 H S2 0), a g nostero l (C30H480), dihydroagnosterol (C 30 H 50 O).
  • Lanolin is available commercially in a number of forms. Lanolin as such contains the active constituents primarily in their ester form. It is also available in two hydrolysed forms where the active constituents are primarily in their alcoholic or carboxylic acid form. Further, lanolin may be hydrogenated to form a product where the active constituents are present primarily only in their alcoholic form. Lanolin is also commercially available in propoxylated and acetylated forms. As used herein the term "lanolin" is intended to refer to any such material derived from wool wax whether the active constituents are in the alcoholic, ester, alkoxylated, hydrogenated or other chemical form.
  • lanolin Suitable commercial forms include Corona (lanolin BP), Hartolan, Polychol and Coronet (Trade Marks of Croda Chemicals Ltd), Solulan, Acetulan and Modulan (Trade Marks of American Cholesterol Products Inc) and Lanocerina (Trade Mark - Esperis SpA Milan).
  • Corona lanolin BP
  • Hartolan Polychol and Coronet
  • Solulan Solulan
  • Acetulan and Modulan Trade Marks of American Cholesterol Products Inc
  • Lanocerina Trade Mark - Esperis SpA Milan.
  • Commercial lanolin is also available from Westbrook Lanolin Co., Bradford, England.
  • lanolin-like material which term as used herein includes
  • the level of lanolin or lanolin-like material in the fabric softening compositions is from 0.25% up to 10% by weight, such as between 0.5% and 5% by weight of the composition.
  • Any well-known cationic fabric softening agent can be used in the present invention, as well as mixtures of two or more of such agents.
  • cationic fabric-softening agents are quaternary ammonium compounds containing two long alkyl or alkenyl chains with 12-22 carbon atoms such as di(hardened or unhardened tallow) dimethyl ammoniumchloride, 2-heptadecyl-2methylstearoyl amido ethyl imidazoline methosulphate, di-(coco)dimethyl ammoniumchloride, etc.
  • cationic fabric-softening agents are well-known in the art and further suitable examples can be found in Schwartz-Perry: "Surface-active Agents and Detergents" Vol II, 1958.
  • Relatively water-soluble cationic softening agents such as the monoalkyl quaternary ammonium compounds such as stearyltrimethylammoniumchloride, may also be used, but, as they are often less effective softeners, they are preferably used in conjunction with other, more effective cationic fabric softening agents or with non-cationic softening agents such as fatty acid esters of polyols such as sorbitantristearate, glycerolmonostearate, and so on, or with anionic detergents with which they are capable of forming softening complexes, such as fatty acid soaps. They may also be made more hydrophobic by treatment with suitable hydrophobising agents such as long chain alcohols and fatty acids. The present invention is however of particular benefit if the more effective, less water-soluble cationic softening agents having two long alkyl chains are used.
  • the level of cationic fabric softening agent in the aqueous fabric softening compositions is at least 0.5% but preferably no more than 30% by weight, such as between 1.0% and 15% by weight of the composition.
  • the ritic by weight of the cationic fabric softening agent to the lanolin or lanolin-like material may lie between 0.05:1 and 20:1, more preferably between 0.1:1 and 10:1, especially between 1:1 and 4:1.
  • the fabric softening composition of the invention is added to a large volume of water to form a liquor with which the fabrics to be treated are contacted.
  • the total concentration of the cationic fabric softening agent and the lanolin or lanolin-like materials in this liquor will be between about 50 ppm and about 500 ppm.
  • the pH of the aqueous composition used for forming the liquor may be varied within a range, for example between about 3 and about 8, preferably from about 4 to about 6.
  • the composition may contain buffering agents as required such as benzoic acid, citric acid and phosphoric acids and/or their alkali metal salts.
  • the fabrics to be treated are contacted with an aqueous liquor to which the fabric softening composition is added, the ratio by weight of the fabrics to the liquor being preferably less than about 25:1, most preferably between about 10:1 and about 4:1.
  • the aqueous liquor in contact with the fabrics may be at any convenient temperature. Successful results can be obtained when the liquor has a temperature between about 0°C and about 60°C, preferably between about 10°C and about 40°C.
  • the liquor and fabrics in contact therewith are preferably agitated during treatment.
  • the amount of cationic softening agent and lanolin or lanolin-like material deposited on the fabric depends on, inter alia, the concentration of these components in the treatment liquor, the treatment temperature, the degree of agitation, the treatment time and the nature of the fabric. Generally, a level of less than about 0.5%, such as between about 0.01% and about 0.4% by weight in total of these components will be deposited, based on the weight of the dry fabric.
  • the balance of the composition comprises the aqueous medium, as the case may be with the other ingredients as set out below.
  • the aqueous medium comprises at least 25%, preferably at least 30%, and especially at least 40% of the composition.
  • compositions of the invention may further comprise additional beneficial ingredients, commonly used or proposed for inclusion in liquid fabric-softening compositions.
  • additional beneficial ingredients commonly used or proposed for inclusion in liquid fabric-softening compositions.
  • Such ingredients include additional viscosity modifiers, germicides, fluorescers, perfumes including deodorising perfumes, organic or inorganic acids, antistatic agents such as water-soluble cationic surfactants, ethoxylated quaternary polyamine compounds (eg Ethoduameen T 13) and aluminium salts, soil-release agents, colourants, antioxidants, bleaches, bleach precursors, anti-yellowing agents, ironing aids etc, all in the conventional minor amounts.
  • Enzymes such as cellulases may also be included.
  • compositions may also contain, in addition to the cationic fabric-softening agents, other non-cationic fabric-softening agents such as nonionic fabric-softening agents.
  • the fabric softening compositions may include a viscosity modifier selected from polymers as described below, C 12 -C 40 hydrocarbons, C 9 -C 24 fatty acids, fatty acid esters having a total of 10-40 carbon atoms, C 10 -C 18 fatty alcohols, water-miscible solvents, and electrolytes.
  • a viscosity modifier selected from polymers as described below, C 12 -C 40 hydrocarbons, C 9 -C 24 fatty acids, fatty acid esters having a total of 10-40 carbon atoms, C 10 -C 18 fatty alcohols, water-miscible solvents, and electrolytes.
  • the polymer when included in the composition of the invention may be present therein in an amount of from 0.5 to 40%, preferably from 1 to 30%, and particularly preferably 4-25%.
  • the polymer, suitable for inclusion, is defined in the following way:
  • the polymer should furthermore have a molecular weight of at least 400, preferably at least 4,000 and particularly preferably at least 6,000.
  • the polymer does not negatively interact with any of the other ingredients of the composition.
  • Suitable examples of the polymer can be thus obtained from the polyalkyleneglycols, the polyalkylene imines, dextran, gelatin and other natural or synthetic (co)polymers, as long as they meet the above criteria.
  • Mixtures of two or more polymers of the same type or of different type may also be used.
  • a preferred class of polymers comprises polyethyleneglycols with an average molecular weight of about 1,000 to about 6,000. These polymers, and especially those with an average molecular weight of 4,000 or 6,000, are particularly suitable for compositions of the invention with a high level of relatively water-insoluble cationic fabric-softening agent.
  • Suitable polymers are dextran with a molecular weight of 10,000 and polyethylene imine with a molecular weight of 45-750.
  • composition contains a C 12 -C 40 hydrocarbon as a viscosity control agent, this is advantageously at a level of from 0.25% to 50% by weight, preferably from 0.5% to 25%.
  • Preferred materials have from 12 to 24 carbon atoms and especially preferred are liquid mixtures of paraffins having from 14 to 18 carbon atoms.
  • suitable hydrocarbons are found in the paraffin and olefin series, but other materials, such as alkynes and cyclic hydrocarbons are not excluded.
  • Materials known generally as paraffin oil, and petroleum are suitable. Examples of specific materials are hexadecane, octadecane, eicosane tetradecane and octadecane.
  • Preferred commercially-available paraffin mixtures include spindle oil and light oil and technical grade mixtures of C 14 -C 18 n-paraffins.
  • Haloparaffins such as myristyl chloride and stearyl bromide are not excluded.
  • composition contains a C 9 -C 24 fatty acid, this is advantageously at a level of from 0.5 to 15%.
  • Highly preferred materials of this class are the C 10- C 20 saturated fatty acids, especially lauric acid, myristic acid, palmitic acid and stearic acid.
  • the composition contains a fatty acid ester having a total of 10 to 40 carbon atoms this is at a preferred level of from 0.25 to 15% by weight, advantageously 0.5 to 4%.
  • the ester is preferably empirically derived from a fatty acid having 8 to 23 carbon atoms and an alkanol or hydroxy alkanol having 1-8, especially 1-4 carbon atoms.
  • esters derived from C l -C 3 alcohols and lauric myristic, palmitic or stearic acid, such as methyl laurate, ethyl myristate, iso-propyl stearate, ethylene glycol monostearate, ethyl stearate, methyl palmitate, and other esters such as iso-butyl stearate and 2-ethylhexyllaurate, iso-octyl myristate.
  • composition contains a fatty alcohol having from 10 to 18 carbon atoms, this is preferably at a level of from 0.25 to 15% by weight.
  • decanol dodecanol
  • tetradecanol pentadecanol
  • hexadecanol octadecanol
  • the most preferred materials are lauryl and palmityl alcohols.
  • a solvent this may be a lower alkanol, a glycol, a glycolether and the like.
  • the solvent may be present at a level of up to 20% by weight, such as from 5% to 15% by weight.
  • the cationic fabric-softening agent is supplied in the form of an aqueous-alcoholic solution, that alcohol content is included in the above amounts, and if necessary only a small amount of extra alcohol is to be added.
  • a suitable solvent is isopropanol.
  • the viscosity of the fabric softening composition may be controlled by the presence of an electrolyte.
  • the electrolyte is a water-soluble non-surface active salt such as sodium chloride, sodium methosulphate, sodium benzoate, calcium chloride, magnesium chloride or aluminium chlorhydrate.
  • the level of electrolyte will determine or be determined by the desired viscosity of the composition and the nature and concentration of other components in the composition. Typical levels are from about 100 to about 1000 parts per million, most preferably between about 200 and about 500 parts per million.
  • the fabric softening compositions optionally contain one or more nonionic emulsifying agents, such as the polymerised monoglycerides of long chain fatty acids having from 14 to 24 carbon atoms in the straight or branched saturated or unsaturated carbon chain, such as noly- monolauryl glyceride, poly-monostearyl glyceride, poly- monopalmityl glyceride or poly-monooleyl glyceride.
  • nonionic emulsifying agents such as the polymerised monoglycerides of long chain fatty acids having from 14 to 24 carbon atoms in the straight or branched saturated or unsaturated carbon chain, such as noly- monolauryl glyceride, poly-monostearyl glyceride, poly- monopalmityl glyceride or poly-monooleyl glyceride.
  • Another suitable nonionic emulsifying agent is sorbitan monostearate.
  • nonionic emulsifying agents are available commercially by the Trade Marks WITCONOL (Witco Chemicals Ltd) and SPAN (Atlas Chemical).
  • the nonionic emulsifying agent may be present at a level from 0.5% to 9.5% by weight, such as from 2.4% to 6%.
  • compositions according to the invention can also include a water-soluble cationic or non-ionic surfactant.
  • water-soluble it is meant that the surfactant has a solubility in water of pH 2.5 and 20°C of greater than 10 g/l.
  • such materials are alkyl substituted ammonium salts having one C 12 -C 24 alkyl chain, optionally substituted or interrupted by functional groups such as -0-, -COO-, -CONH-, -O- etc.
  • Suitable water-soluble nonionic surfactants are the ethoxylates, sorbitan esters available as TWEENS (Atlas Chemical).
  • a water-soluble cationic or nonionic emulsifying agent in the composition if it contains as a viscosity modifier a hydrocarbon, fatty acid, fatty alcohol or fatty acid ester of the types referred to above.
  • the level of the water-soluble surfactant is preferably 0.01% to 1%.
  • the compositions contain substantially no anionic material such as anionic surfactants. However some anionic material may be tolerated in practice.
  • the weight ratio of anu anionic material to the cationic fabric softening agent is less 5than 0.4:1, most preferably less than 0.2:1.
  • the viscosity of the fabric softening compositions is preferably less than about 150 cP, most preferably less than about 120 cP. This viscosity is measured at 25'C and 110 sec -1 in a Haake Viscometer.
  • compositions of the invention can normally be prepared by mixing the ingredients together in water, heating to a temperature of about 60°C and agitating for 5-30 minutes.
  • Fabric conditioning compositions were made up according to the formulations given in the following Tables I and II by mixing the ingredients together in water at about 60°C and agitating.
  • the cationic fabric softening agents used were:
  • the lanolin used in each case was pure lanolin BP (ex BDM).
  • the viscosity modifying agents used were:
  • the water-soluble emulsifying agent used was Arquad 18 (50% active).
  • Each Table also gives the viscosity of the composition as measure in a Haake viscometer at 110 sec -1 and at 25°C.
  • Fabric conditioning compositions were made up according to the formulations given in the following Table III by mixing the ingredients together in water at about 60°C and agitating. Product viscosities were measured as in Examples 1 to 13.
  • Pieces of cotton terry cloth were treated with liquors made up from these compositions.
  • the treated cloths were assessed by a panel of people who found that composition B gave more preferred results than composition A.

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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)
  • Zoology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP83300625A 1982-02-10 1983-02-08 Composition d'adoucissage pour matières textiles Expired EP0088520B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83300625T ATE42570T1 (de) 1982-02-10 1983-02-08 Textilweichmacherzusammensetzung.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8203881 1982-02-10
GB8203881 1982-02-10

Publications (3)

Publication Number Publication Date
EP0088520A2 true EP0088520A2 (fr) 1983-09-14
EP0088520A3 EP0088520A3 (en) 1986-02-26
EP0088520B1 EP0088520B1 (fr) 1989-04-26

Family

ID=10528228

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83300625A Expired EP0088520B1 (fr) 1982-02-10 1983-02-08 Composition d'adoucissage pour matières textiles

Country Status (14)

Country Link
EP (1) EP0088520B1 (fr)
JP (1) JPS58149380A (fr)
AT (1) ATE42570T1 (fr)
BR (1) BR8300643A (fr)
CA (1) CA1192003A (fr)
DE (1) DE3379733D1 (fr)
GB (1) GB2114618B (fr)
GR (1) GR77963B (fr)
IN (1) IN156622B (fr)
NO (1) NO830421L (fr)
PH (1) PH17958A (fr)
PT (1) PT76218B (fr)
ZA (1) ZA83878B (fr)
ZW (1) ZW3583A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0107479A2 (fr) * 1982-10-21 1984-05-02 Unilever Plc Composition pour le conditionnement de matières textiles
EP0159918A2 (fr) * 1984-04-19 1985-10-30 Unilever Plc Composition adoucissante pour tissus
WO2008040785A1 (fr) * 2006-10-06 2008-04-10 Dow Corning Corporation Procédé de préparation de compositions assouplissantes

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2202184A1 (en) * 1972-10-10 1974-05-03 Colgate Palmolive Co Fabric softening aerosol compsn - lanoline deriv, foaming agent, fluid medium and liquefied gas
DE2360408A1 (de) * 1972-12-05 1974-06-12 Unilever Nv Reinigungsmittelzusammensetzung
US4110498A (en) * 1976-03-08 1978-08-29 The Procter & Gamble Company Fabric treatment compositions
GB2007734A (en) * 1977-10-22 1979-05-23 Cargo Fleet Chemical Co Fabric softeners
EP0013780A1 (fr) * 1979-01-11 1980-08-06 THE PROCTER & GAMBLE COMPANY Composition concentrée d'adoucissement pour tissus

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2202184A1 (en) * 1972-10-10 1974-05-03 Colgate Palmolive Co Fabric softening aerosol compsn - lanoline deriv, foaming agent, fluid medium and liquefied gas
DE2360408A1 (de) * 1972-12-05 1974-06-12 Unilever Nv Reinigungsmittelzusammensetzung
US4110498A (en) * 1976-03-08 1978-08-29 The Procter & Gamble Company Fabric treatment compositions
GB2007734A (en) * 1977-10-22 1979-05-23 Cargo Fleet Chemical Co Fabric softeners
EP0013780A1 (fr) * 1979-01-11 1980-08-06 THE PROCTER & GAMBLE COMPANY Composition concentrée d'adoucissement pour tissus

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Encyclopedia of Chemical Technology, Kirk-Othmer, 3rd ed., vol. 24, J. Wiley & Son (1984), pp. 636-639 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0107479A2 (fr) * 1982-10-21 1984-05-02 Unilever Plc Composition pour le conditionnement de matières textiles
EP0107479A3 (en) * 1982-10-21 1986-03-19 Unilever Plc Fabric conditioning composition
EP0159918A2 (fr) * 1984-04-19 1985-10-30 Unilever Plc Composition adoucissante pour tissus
EP0159918A3 (fr) * 1984-04-19 1986-12-30 Unilever Plc Composition adoucissante pour tissus
WO2008040785A1 (fr) * 2006-10-06 2008-04-10 Dow Corning Corporation Procédé de préparation de compositions assouplissantes
US8242071B2 (en) 2006-10-06 2012-08-14 Dow Corning Corporation Process for preparing fabric softener compositions

Also Published As

Publication number Publication date
ZA83878B (en) 1984-09-26
ZW3583A1 (en) 1984-08-29
GB2114618B (en) 1986-05-21
EP0088520A3 (en) 1986-02-26
EP0088520B1 (fr) 1989-04-26
IN156622B (fr) 1985-09-21
BR8300643A (pt) 1983-11-08
JPS58149380A (ja) 1983-09-05
PT76218B (en) 1986-07-14
GB8303393D0 (en) 1983-03-16
GR77963B (fr) 1984-09-25
PH17958A (en) 1985-02-20
PT76218A (en) 1983-03-01
GB2114618A (en) 1983-08-24
NO830421L (no) 1983-08-11
CA1192003A (fr) 1985-08-20
ATE42570T1 (de) 1989-05-15
DE3379733D1 (en) 1989-06-01

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