EP0885278B1 - Fabric softening composition - Google Patents

Fabric softening composition Download PDF

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Publication number
EP0885278B1
EP0885278B1 EP97904366A EP97904366A EP0885278B1 EP 0885278 B1 EP0885278 B1 EP 0885278B1 EP 97904366 A EP97904366 A EP 97904366A EP 97904366 A EP97904366 A EP 97904366A EP 0885278 B1 EP0885278 B1 EP 0885278B1
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EP
European Patent Office
Prior art keywords
fabric softening
alkyl
group
softening composition
composition according
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Expired - Lifetime
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EP97904366A
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German (de)
French (fr)
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EP0885278A1 (en
Inventor
Ailsa Pauline Hilary Grieveson
Christopher Whaley
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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Classifications

    • 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
    • C11D1/38Cationic compounds
    • C11D1/65Mixtures of anionic with cationic 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
    • C11D1/835Mixtures of non-ionic with cationic 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
    • C11D1/86Mixtures of anionic, cationic, and non-ionic 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2093Esters; Carbonates
    • 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
    • C11D1/04Carboxylic acids or salts thereof
    • 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
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium 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
    • C11D1/667Neutral esters, e.g. sorbitan esters

Definitions

  • This invention relates to fabric softening compositions containing a skin benefit agent such that when fabrics are treated with the fabric softening composition when in contact with the skin the fabrics deliver the skin benefit agent to the skin
  • Rinse added fabric softener compositions are well known. Typically such compositions contain a water insoluble amine salt and/or a quaternary ammonium fabric softening agent dispersed in water at a level of softening agent up to 7% by weight in which case the compositions are considered dilute, or at levels from 7% to 50% in which case the compositions are considered concentrates. Quaternary ammonium materials with long chain substituents have been used in fabric softening compositions for many years. Often they are used in conjunction with co-actives such as fatty acids or other relatively cheap materials which also provide softening benefits.
  • fabric softening compositions desirably have other benefits.
  • GB 1 601 359 Procter and Gamble
  • GB 1 550 205 Procter and Gamble
  • ester oil and silicones as an ingredient in a fabric softening composition as fabric lubricants suggested which may give ease of ironing benefits, and softening.
  • EP 0 436 729 discloses an industrial process for applying microcapsules to fabric, which when contacted with the skin are physiologically active.
  • the present invention provides a fabric softening composition
  • a fabric softening composition comprising a skin conditioning compound comprising a C 8 -C 22 ⁇ -hydroxyacid, an ester of a ⁇ -hydroxyacid or mixtures thereof and a biodegradable, fabric softening quaternary ammonium compound as defined in claim 1.
  • a fabric treatment composition such that skin is conditioned when fabrics treated with said composition come into contact with the skin.
  • the skin conditioning agent is an ⁇ -hydroxy carboxylic acid or ester or mixtures thereof. It is further preferred if the skin conditioning agent is represented by formula I: R 1 - [0-CH(R 3 )-CO] m -OR 2
  • R 1 is H or a C 10 -C 22 acyl group and R 2 is H, a C 10 -C 22 alkyl group, or a compatible counterion, for example sodium, potassium, or quaternary ammonium
  • R 3 is hydrogen or C 1 -C 20 alkyl group and m is equal to 1 or 10 with the proviso that if R 1 and R 2 are both hydrogen R 3 is C 6 - C 20 alkyl group.
  • Preferred ⁇ -hydroxyacids and esters for use with the invention may be represented by formula II and include glycollic acid esters, alkyl lactates, acyl lactylates, citric acid esters, tartaric acid esters, ⁇ -hydroxycaprylic acid esters, and long chain ⁇ -hydroxyacids (greater than or equal to 8 carbon atoms), for example ⁇ -hydroxycaprylic acid.
  • R 1 is H or a C 10 -C 22 acyl group and R 2 is H, a C 10 -C 22 alkyl group, or a compatible counterion, for example sodium, potassium, or quaternary ammonium, with the proviso that R 1 and R 2 cannot both be H.
  • ⁇ -hydroxyacid ester is an alkyl lactate or acyl lactylate.
  • the level of acyl lactylate or alkyl lactate is preferably 5 to 30 wt%, most preferably 10 to 25wt% of the total composition.
  • compositions according to the invention contain a quaternary ammonium fabric softeners compound.
  • the fabric softening composition comprises a water insoluble cationic compound having two C 12-28 alkyl or alkenyl groups. It is especially preferred if these C 12-28 alkyl or alkenyl groups are connected to the N atom via one or more ester links.
  • ester-linked quaternary ammonium material used in the compositions according to the invention is represented by the formula:
  • each R 4 group is independently selected from C 1-4 alkyl, hydroxyalkyl groups or C 2-4 alkenyl groups; wherein each R 5 group is independently selected from C 8-28 alkyl or alkenyl groups;
  • X - is a suitable counter ion and n is o or an integer from 1-5.
  • a further type of cationic softener used in the composition according to the invention is represented by the formula: wherein each R 6 group is independently selected from C 1-4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein each R 7 group is independently selected from C 8-28 alkyl or alkenyl groups;
  • ester linked quaternary ammonium materials with the above formula is that when fabric softening compositions containing them have excellent viscosities and are stable on storage.
  • the level of ester linked quaternary ammonium compounds is at least 1% by weight of the composition, more preferably at least 3% by weight of the composition; especially interesting are concentrated compositions which comprise at least 7% of ester-linked quaternary ammonium compound.
  • the level of ester-linked quaternary ammonium compounds preferably is from 1% to 80% by weight, more preferably from 4% to 32%, most preferably from 6% to 22%.
  • the ratio of fabric softening compound to acyl lactylate/alkyl lactate is preferably from 0.5:1 to 1:5, more preferably from 1:1 to 1:4.
  • the softening composition may also comprise a nonionic stabilising agent selected from:
  • the nonionic stabilising agent is a linear C 8 to C 22 alcohol alkoxylated with 10 to 20 moles of alkylene oxide.
  • the nonionic stabiliser has an HLB value of from 10 to 20, more preferably from 12 to 20.
  • the level of nonionic stabiliser is within the range from 0 to 10% by weight, more preferably from 0 to 5% by weight, most preferably from 0 to 4% by weight.
  • the mole ratio of the quaternary ammonium compound to the nonionic stabilising agent is within the range from 40:1 to 1:1, preferably within the range from 18:1 to 3:1.
  • compositions of the invention are liquids comprising an aqueous base.
  • the composition can also contain a co-active for example a C 8 - C 24 alkyl or alkenyl monocarboxylic acid or polymer thereof.
  • a co-active for example a C 8 - C 24 alkyl or alkenyl monocarboxylic acid or polymer thereof.
  • saturated fatty acids are used, in particular, hardened tallow (C 16 -C 18) fatty acids.
  • the fatty acid is non-saponified, for example free oleic acid, lauric acid or tallow fatty acid.
  • Lanolin or other nonionic fabric softening agents may also be used as co-actives.
  • the level of co-active material is preferably more than 0.1% by weight, more preferably more than 0.2% by weight. Especially preferred are concentrates comprising from 0.5 to 20% by weight of co-active, more preferably 1% to 10% by weight.
  • the weight ratio of quaternary ammonium/amine material to co-active material is preferably from 10:1 to 1:10.
  • composition can also contain one or more optional ingredients, selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, soil release agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, and antistatic agents.
  • optional ingredients selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, soil release agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, and antistatic agents.
  • a fabric softening composition comprising:
  • a fabric softening composition comprising:
  • the fabric softening compositions of the Examples were prepared by heating admixtures of cationic/fatty acid to above 70°C in lauryl lactate and slowly adding the mixture to hot demineralised water with vigorous shear.
  • a comparative example containing 4.29% quaternary ammonium cationic and 0.71 wt% fatty acid was prepared in a similar manner.

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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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

  • This invention relates to fabric softening compositions containing a skin benefit agent such that when fabrics are treated with the fabric softening composition when in contact with the skin the fabrics deliver the skin benefit agent to the skin
  • Rinse added fabric softener compositions are well known. Typically such compositions contain a water insoluble amine salt and/or a quaternary ammonium fabric softening agent dispersed in water at a level of softening agent up to 7% by weight in which case the compositions are considered dilute, or at levels from 7% to 50% in which case the compositions are considered concentrates. Quaternary ammonium materials with long chain substituents have been used in fabric softening compositions for many years. Often they are used in conjunction with co-actives such as fatty acids or other relatively cheap materials which also provide softening benefits.
  • In addition to softening, fabric softening compositions desirably have other benefits.
  • GB 1 601 359 ( Procter and Gamble ) and GB 1 550 205 (Procter and Gamble) describes the use of ester oil and silicones as an ingredient in a fabric softening composition as fabric lubricants suggested which may give ease of ironing benefits, and softening.
  • EP 0 436 729 (Kanebo) discloses an industrial process for applying microcapsules to fabric, which when contacted with the skin are physiologically active.
  • Accordingly the present invention provides a fabric softening composition comprising a skin conditioning compound comprising a C8-C22 α-hydroxyacid, an ester of a α-hydroxyacid or mixtures thereof and a biodegradable, fabric softening quaternary ammonium compound as defined in claim 1.
  • In a second aspect of the present invention there is also provided the use of an α-hydroxyacid, or an ester thereof, in a fabric treatment composition such that skin is conditioned when fabrics treated with said composition come into contact with the skin.
  • It is preferred if the skin conditioning agent is an α-hydroxy carboxylic acid or ester or mixtures thereof. It is further preferred if the skin conditioning agent is represented by formula I: R1- [0-CH(R3)-CO]m-OR2
  • In which R1 is H or a C10-C22 acyl group and R2 is H, a C10-C22 alkyl group, or a compatible counterion, for example sodium, potassium, or quaternary ammonium, R3 is hydrogen or C1-C20 alkyl group and m is equal to 1 or 10 with the proviso that if R1 and R2 are both hydrogen R3 is C6- C20 alkyl group.
  • Preferred α-hydroxyacids and esters for use with the invention may be represented by formula II and include glycollic acid esters, alkyl lactates, acyl lactylates, citric acid esters, tartaric acid esters, α-hydroxycaprylic acid esters, and long chain α-hydroxyacids (greater than or equal to 8 carbon atoms), for example α-hydroxycaprylic acid. R1-O-CH(CH3)CO.OR2
  • In which R1 is H or a C10-C22 acyl group and R2 is H, a C10-C22 alkyl group, or a compatible counterion, for example sodium, potassium, or quaternary ammonium, with the proviso that R1 and R2 cannot both be H.
  • It is especially preferred if the α-hydroxyacid ester is an alkyl lactate or acyl lactylate.
  • The level of acyl lactylate or alkyl lactate is preferably 5 to 30 wt%, most preferably 10 to 25wt% of the total composition.
  • Compositions according to the invention contain a quaternary ammonium fabric softeners compound. Advantageously the fabric softening composition comprises a water insoluble cationic compound having two C12-28 alkyl or alkenyl groups. It is especially preferred if these C12-28 alkyl or alkenyl groups are connected to the N atom via one or more ester links.
  • One type of ester-linked quaternary ammonium material used in the compositions according to the invention is represented by the formula:
    Figure 00040001
  • In which each R4 group is independently selected from C1-4 alkyl, hydroxyalkyl groups or C2-4 alkenyl groups; wherein each R5 group is independently selected from C8-28 alkyl or alkenyl groups; X- is a suitable counter ion and n is o or an integer from 1-5.
  • Materials of this class and their method of preparation are described in US 4 137 180 (Lever Brothers). Analysis of such materials shows that they also comprise small amounts of the corresponding dimethylamine salt, one such salt being N,N-dimethyl-2,3-bis[hardened tallowoyloxy]-propylamine hydrochloride. Advantageously these materials comprise small amounts of the corresponding monoester as described in US 4 137 180, for example, 1-hardened tallowoyloxy-2-hydroxy-3-trimethylammonium propane chloride.
  • A further type of cationic softener used in the composition according to the invention is represented by the formula:
    Figure 00050001
    wherein each R6 group is independently selected from C1-4 alkyl, hydroxyalkyl or C2-4alkenyl groups; and wherein each R7 group is independently selected from C8-28 alkyl or alkenyl groups;
  • T is
    Figure 00050002
    and
  • n is o or an integer from 1-5 and X- is any suitable anion.
  • A further advantage of using ester linked quaternary ammonium materials with the above formula is that when fabric softening compositions containing them have excellent viscosities and are stable on storage.
  • Preferably the level of ester linked quaternary ammonium compounds is at least 1% by weight of the composition, more preferably at least 3% by weight of the composition; especially interesting are concentrated compositions which comprise at least 7% of ester-linked quaternary ammonium compound. The level of ester-linked quaternary ammonium compounds preferably is from 1% to 80% by weight, more preferably from 4% to 32%, most preferably from 6% to 22%.
  • The ratio of fabric softening compound to acyl lactylate/alkyl lactate is preferably from 0.5:1 to 1:5, more preferably from 1:1 to 1:4.
  • The softening composition may also comprise a nonionic stabilising agent selected from:
  • i. linear C8 to C22 alcohol alkoxylated with 10 to 20 moles of alkylene oxide; and
  • ii. a C10 to C20 alcohol or mixtures thereof.
  • Advantageously the nonionic stabilising agent is a linear C8 to C22 alcohol alkoxylated with 10 to 20 moles of alkylene oxide. Preferably the nonionic stabiliser has an HLB value of from 10 to 20, more preferably from 12 to 20.
  • Preferably, the level of nonionic stabiliser is within the range from 0 to 10% by weight, more preferably from 0 to 5% by weight, most preferably from 0 to 4% by weight. When nonionic stabilising agent is present the mole ratio of the quaternary ammonium compound to the nonionic stabilising agent is within the range from 40:1 to 1:1, preferably within the range from 18:1 to 3:1.
  • Preferably the compositions of the invention are liquids comprising an aqueous base.
  • The composition can also contain a co-active for example a C8 - C24 alkyl or alkenyl monocarboxylic acid or polymer thereof. Preferably saturated fatty acids are used, in particular, hardened tallow (C16-C18) fatty acids. Preferably the fatty acid is non-saponified, for example free oleic acid, lauric acid or tallow fatty acid. Lanolin or other nonionic fabric softening agents may also be used as co-actives.
  • The level of co-active material is preferably more than 0.1% by weight, more preferably more than 0.2% by weight. Especially preferred are concentrates comprising from 0.5 to 20% by weight of co-active, more preferably 1% to 10% by weight. The weight ratio of quaternary ammonium/amine material to co-active material is preferably from 10:1 to 1:10.
  • The composition can also contain one or more optional ingredients, selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, soil release agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, and antistatic agents.
  • The invention will now be illustrated by the following nonlimiting examples. In the examples all percentages are expressed by weight.
  • Example 1
  • A fabric softening composition comprising:
  • 4.29 wt% quaternary ammonium cationic1
  • 0.71 wt% fatty acid2
  • 15.00 wt% lauryl lactate3
  • to 100 wt% water and minors
  • Example 2
  • A fabric softening composition comprising:
  • 4.29 wt% quaternary ammonium cationic1
  • 0.71 wt% fatty acid2
  • 10.00 wt% lauryl lactate3
  • to 100 wt% water and minors
  • Preparation of Examples
  • The fabric softening compositions of the Examples were prepared by heating admixtures of cationic/fatty acid to above 70°C in lauryl lactate and slowly adding the mixture to hot demineralised water with vigorous shear.
  • A comparative example containing 4.29% quaternary ammonium cationic and 0.71 wt% fatty acid was prepared in a similar manner.
  • The Comparative Example and Example 1 were used to treat terry towelling in 1L tergotometer pots (liquor:cloth = 40:1, ambient temperature, 5 mins., 65 rpm). The terry towelling was spun to remove excess liquor and then line dried. The treated terry towelling pieces were rubbed onto the front forearms of the panellist for one minute. Tape strips samples of the skin surface were taken and analysed for lactate content using a standard method involving Sigma 735-10 lactate reagent. The results are shown in the Table below and clearly illustrate the increased level of lactate found on using the formulation of Example 1.
    Example Dosage (ml) Lactate (µg/cm2)
    1 0.67 1.11
    Comparative 2 0.43
    1 1.33 0.95
    Comparative 4 0.33

Claims (8)

  1. A fabric softening composition characterised in that it comprises:
    i) a skin conditioning compound comprising a C8-C22 α-hydroxyacid, an ester of a α-hydroxyacid or mixtures thereof and;
    ii) a biodegradable, fabric softening quaternary ammonium compound represented by the formula:
    Figure 00100001
    in which each R4 group is independently selected from C1-4 alkyl, hydroxyalkyl groups or C2-4 alkenyl groups; wherein each R5 group is independently selected from C8-28 alkyl or alkenyl groups; X- is a suitable counter ion and n is o or an integer from 1-5, or by the formula:
    Figure 00100002
    wherein each R6 group is independently selected from C1-4 alkyl, hydroxyalkyl or C2-4 alkenyl groups; and wherein each R7 group is independently selected from C8-28 alkyl or alkenyl groups;
    T is
    Figure 00110001
    and n and X- are as defined above.
  2. A fabric softening composition according to claim 1 in which the skin conditioning agent is represented by the formula: R1-[0-CH(R3)-CO]m-OR2 in which R1 is H or a C10-C22 acyl group and R2 is H, a C10-C22 alkyl group, or a compatible counterion, for example sodium, potassium, or quaternary ammonium, R3 is hydrogen or C1-C20 alkyl group and m is equal to 1 or 10 with the proviso that if R1 and R2 are both hydrogen R3 is C6- C20. alkyl group.
  3. A fabric softening composition according to any preceding claim in which the skin conditioning compound is an acyl lactylate or an alkyl lactate or mixtures thereof.
  4. A fabric softening composition according to any preceding claim in which the alkyl lactate or acyl lactylate has the following formula: R1-O-CH(CH3)CO.OR2 in which R1 is H or a C10-C22 acyl group and R2 is H, a C10-C22 alkyl group, or a compatible counterion, for example sodium, potassium, or quaternary ammonium, with the proviso that R1 and R2 cannot both be H.
  5. A fabric softening composition according to any preceding claim in which the level of skin conditioning compound is from 5 to 30 wt%.
  6. A fabric softening composition according to any preceding claim in which the ratio of fabric softening compound to skin conditioning compound is in the range from 1:1 to 1:5.
  7. Use of an α-hydroxyacid or esters thereof in a fabric softening composition as defined in any proceeding claim such that skin is conditioned when fabrics treated with the composition come into contact with the skin.
  8. Use of an α-hydroxyacid ester in a fabric softening composition according to claim 7 in which the α-hydroxyacid ester is an alkyl lactate or an acyl lactylate.
EP97904366A 1996-02-09 1997-01-28 Fabric softening composition Expired - Lifetime EP0885278B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9602619 1996-02-09
GBGB9602619.0A GB9602619D0 (en) 1996-02-09 1996-02-09 Fabric softening composition
PCT/EP1997/000452 WO1997029171A1 (en) 1996-02-09 1997-01-28 Fabric softening composition

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Publication Number Publication Date
EP0885278A1 EP0885278A1 (en) 1998-12-23
EP0885278B1 true EP0885278B1 (en) 2001-08-29

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EP (1) EP0885278B1 (en)
JP (1) JP2000504754A (en)
AR (1) AR005743A1 (en)
AU (1) AU1720797A (en)
BR (1) BR9707273A (en)
CA (1) CA2246060C (en)
DE (1) DE69706405T2 (en)
ES (1) ES2163121T3 (en)
GB (1) GB9602619D0 (en)
WO (1) WO1997029171A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19651447C1 (en) * 1996-12-11 1997-10-02 Henkel Kgaa Textile or hair conditioners having improved performance
DE19708133C1 (en) * 1997-02-28 1997-12-11 Henkel Kgaa Conditioner for textile and keratin fibres useful as e.g. laundry or hair conditioner
CN106739279A (en) * 2016-12-02 2017-05-31 常熟市隆通金属制品有限公司 A kind of precision optical machinery composite metal product

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4559151A (en) * 1984-05-07 1985-12-17 Sterling Drug Inc. Antistatic fabric conditioner compositions and method
MY100841A (en) * 1986-04-25 1991-03-15 Kao Corp Hair cosmetic composition
JPH0625090B2 (en) * 1987-02-12 1994-04-06 花王株式会社 Hair cosmetics
JPH0386798A (en) * 1989-08-29 1991-04-11 Regurusu:Kk Dry-cleaning solvent
JPH0423900A (en) * 1990-05-16 1992-01-28 Kao Corp Detergent composition
DE4111966A1 (en) * 1991-04-12 1992-10-15 Henkel Kgaa USE OF ESTERS AS A TEXTILE WEIGHTING AGENT

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DE69706405D1 (en) 2001-10-04
AR005743A1 (en) 1999-07-14
DE69706405T2 (en) 2002-06-20
EP0885278A1 (en) 1998-12-23
AU1720797A (en) 1997-08-28
BR9707273A (en) 1999-04-13
WO1997029171A1 (en) 1997-08-14
JP2000504754A (en) 2000-04-18
CA2246060C (en) 2004-04-13
ES2163121T3 (en) 2002-01-16
CA2246060A1 (en) 1997-08-14
GB9602619D0 (en) 1996-04-10

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