CA2246060C - Fabric softening composition - Google Patents

Fabric softening composition Download PDF

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Publication number
CA2246060C
CA2246060C CA002246060A CA2246060A CA2246060C CA 2246060 C CA2246060 C CA 2246060C CA 002246060 A CA002246060 A CA 002246060A CA 2246060 A CA2246060 A CA 2246060A CA 2246060 C CA2246060 C CA 2246060C
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CA
Canada
Prior art keywords
fabric softening
alkyl
group
softening composition
hydroxyacid
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.)
Expired - Fee Related
Application number
CA002246060A
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French (fr)
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CA2246060A1 (en
Inventor
Ailsa Pauline Hilary Grieveson
Christopher Whaley
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Sun Products Corp
Original Assignee
Unilever PLC
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Filing date
Publication date
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Publication of CA2246060A1 publication Critical patent/CA2246060A1/en
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Anticipated expiration legal-status Critical
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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

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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)

Abstract

A fabric softening composition which comprises a skin conditioning compound comprising a C8-C22 .alpha.-hydroxyacid or an ester of a .alpha.-hydroxyacid or mixtures thereof and a fabric softening compound. The fabric conditioner when used to condition fabrics causes the fabrics to condition skin when contacted therewith.

Description

Fabric Softenina Composition 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 7o by weight in which case the compositions are considered dilute, or at levels from 7~ to 50o 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.
r Accordingly the present invention provides a fabric softening composition comprising a skin conditioning compound comprising a C8-C22 a-hydroxyacid, an ester of a OG-hydroxyacid or mixtures thereof and a fabric softening compound comprising a quaternary ammonium softening material.
In a second aspect of the present invention there is also provided the use of an ~G-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.
2t is preferred if the skin conditioning agent is an ~-hydroxy carboxylic acid or ester or mixtures thereof. Zt is further preferred if the skin conditioning agent is represented by formula I:
R1- [ 0 -CH ( R3 ) -CO ] ,n-ORa Formula I
In which R1 is H or a Clo-C22 acyl group and Ra is H, a Clo-C2a alkyl group, or a compatible counterion, for example sodium, ' potassium, or quaternary ammonium, R3 is hydrogen or C1-C2o and m is equal to 1 or 10 with the proviso that if R1 and RZ
are both hydrogen R3 is C6- C2o..

WO 97/29171 PCT/EP9?/00452 Preferred GG-hydroxyacids and esters for use with the invention may be represented by formula II and include glycollic acid esters, alkyl lactates, aryl lactylates, citric acid esters, tartaric acid esters, Ot-hydroxycaprylic acid esters, and long chain Ct-hydroxyacids (greater than or equal to 8 carbon atoms?, for example a-hydroxycaprylic acid.
R1-O-CH ( CH3 ) CO . ORZ
Formula II
In which R1 is H or a Clo-C22 acyl group and RZ is H, a Clo-Caa alkyl group, or a compatible counterion, for example sodium, potassium, or quaternary ammonium, with the proviso that Rl and Ra cannot both be H.
It is especially preferred if the a-hydroxyacid ester is an alkyl lactate or aryl lactylate.
The level of acyl lactylate or alkyl lactate is preferably 5 to 30 wtg, 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 which is a compound having two C12_2s alkyl or alkenyl r groups, if is especially preferred if these C12-za alkyl or alkenyl groups are connected to the N atom via one or more ester links.
A preferred type of ester-linked quaternary ammonium material for use in the compositions according to the invention can be represented by the formula:
OCORS
( R'° ) 3N~ - ( CHa } n CH X-In which each Rg group is independently selected from C1_g alkyl, hydroxyalkyl groups or Ca_~ alkenyl groups; wherein each R' group is independently selected from C8_z$ 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 preferred cationic softener is represented by the formula i _ 5 -Rs I
E
Rs N~ (CHZ)n-T-R' X_ I
( CH2 ) n-T-R' wherein each Rs group is independently selected from C1_~
alkyl, hydroxyalkyl or Ca_4alkenyl groups; and wherein each R' group is independently selected from C8_2$ alkyl or alkenyl groups;
O O
II II
T is -O-C- or -C-O-; 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 2~ 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 320, most preferably from 6~ to 22~.

WO 97!29171 PCT/EP97/00452 The ratio of fabric softening compound to aryl 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 C$ to C22 alcohol alkoxylated with 10 to 20 moles of alkylene oxide; and ii. a C1Q to C2o alcohol or mixtures thereof.
Advantageously the nonionic stabilising agent is a linear C8 to Cz2 alcohol alkoxylated with 10 to 20 moles of aikylene oxide. Preferably the nonionic stabiliser has an HLB value of from 20 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 - C~4 alkyl or alkenyl monocarboxylic acid or polymer thereof. Preferably saturated fatty acids are used, in _ 7 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-shrinlsing agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, and antistatic agents.
The invention will now be illustrated by the following non-limiting examples. In the examples all percentages are expressed by weight.
A fabric softening composition comprising:
4.29 wt$ quaternary ammonium cationicl 0.72 wt$ fatty acid2 15.00 wt$ lauryl lactate3 to 100 wt$ water and minors _ g _ A fabric softening composition comprising:
4.29 wt~ quaternary ammonium cationicl 0.71 wt~ fatty acid2 10.00 wt~ lauryl lactate3 to 100 wt% water and minors .~~enaration of Examples The fabric softening compositions of the Examples were prepared by heating admixtures of cationic/fatty acid to above 70°C in lauzyl lactate and slowly adding the mixture to hot demineralised water with vigorous shear.
A comparative example containing 4.29 quaternary ammonium cationicl and 0.71 wto fatty acids was prepared in a similar manner.
1 is 1,2 bis[hardened tallowoyloxyl-3-trimethylammonium propane chloride - ex Hoeschst 2 is Hardened tallow fatty acid - ex Hoeschst 3 is Crodamol LL -ex Croda l 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 _ g _ clearly illustrate the increased level of lactate found on using the formulation of Example 1.
Example ~ Dosage (ml) Lactate (ug/cm21 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 .alpha.-hydroxyacid, an ester of a .alpha.-hydroxyacid or mixtures thereof and;
ii) a biodegradable, fabric softening quaternary ammonium compound represented by the formula:
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 counterion and n is o or an integer from 1-5, or by the formula:
wherein each R6 group is independently selected from C1-4 alkyl, hydroxyalkyl or C2-4 alkenyl groups; and wherein each R' group is independently selected from C8-28 alkyl or alkenyl groups;
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-[O-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 claim 1 or 2, 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 one of claims 1 to 3, 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 one of claims 1 to 4, in which the level of skin conditioning compound is from 5 to 30 wt%.
6. A fabric softening composition according to any one of claims 1 to 5, 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 .alpha.-hydroxyacid or esters thereof in a fabric softening composition as defined by any one of claims 1 to 6, such that skin is conditioned when fabrics treated with the composition come into contact with the skin.
8. Use of an .alpha.-hydroxyacid ester in a fabric softening composition according to claim 7, in which the .alpha.-hydroxyacid ester is an alkyl lactate or an acyl lactylate.
CA002246060A 1996-02-09 1997-01-28 Fabric softening composition Expired - Fee Related CA2246060C (en)

Applications Claiming Priority (3)

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

Publications (2)

Publication Number Publication Date
CA2246060A1 CA2246060A1 (en) 1997-08-14
CA2246060C true CA2246060C (en) 2004-04-13

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CA002246060A Expired - Fee Related CA2246060C (en) 1996-02-09 1997-01-28 Fabric softening composition

Country Status (10)

Country Link
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)

Families Citing this family (3)

* 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

Family Cites Families (6)

* 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

Also Published As

Publication number Publication date
JP2000504754A (en) 2000-04-18
GB9602619D0 (en) 1996-04-10
AR005743A1 (en) 1999-07-14
WO1997029171A1 (en) 1997-08-14
DE69706405D1 (en) 2001-10-04
AU1720797A (en) 1997-08-28
BR9707273A (en) 1999-04-13
ES2163121T3 (en) 2002-01-16
CA2246060A1 (en) 1997-08-14
EP0885278B1 (en) 2001-08-29
DE69706405T2 (en) 2002-06-20
EP0885278A1 (en) 1998-12-23

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