CA2233229C - Fabric softening composition - Google Patents

Fabric softening composition Download PDF

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Publication number
CA2233229C
CA2233229C CA002233229A CA2233229A CA2233229C CA 2233229 C CA2233229 C CA 2233229C CA 002233229 A CA002233229 A CA 002233229A CA 2233229 A CA2233229 A CA 2233229A CA 2233229 C CA2233229 C CA 2233229C
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Prior art keywords
fabric softening
ester
quaternary ammonium
softening composition
nonionic
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Expired - Fee Related
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CA002233229A
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French (fr)
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CA2233229A1 (en
Inventor
Graham Andrew Turner
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Unilever PLC
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Unilever PLC
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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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • 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
    • C11D1/38Cationic 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
    • C11D1/662Carbohydrates 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
    • C11D1/667Neutral 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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

An aqueous fabric softening composition comprising: (a) a water insoluble, quaternary ammonium material comprising at least one ester link and two C12-28 alkyl or alkenyl groups, and (b) a sucrose ester or an alkyl polyglucoside.

Description

Field of the Invention The present invention relates to a fabric softening composition, in particular the invention relates to aqueous dispersions of fabric softening compositions comprising a water insoluble quaternary ammonium material and a nonionic stabilising agent suitable as rinse-added fabric softener compositions.

Backaround of the Invention Rinse added fabric softeners are known. Typically such compositions contain a water insoluble quaternary ammonium fabric softening agent dispersed in water at a level of softening agent up to about 7 wt%, in which case the compositions are considered dilute, or at levels from 7 wt%
to 50 wt%, in which case the compositions are known as concentrates.

The viscosity of fabric softener may be seen by the consumer as an important attribute. For this reason thickening polymers are added to compositions, for example EP 0 331 237 (Unilever) discloses the use of hydrophobically modified nonionic cellulose ether for use as a thickener for fabric conditioning compositions containing quaternary ammonium cations.
There are however negative attributes associated with many polymeric thickeners in that they are not biodegradable, their addition to the rinse product is technically difficult and the viscosity of such polymer thickened products tends to increase with time.

= C3685 - 2 -In US 4 137 180 (Lever Brothers Company) discloses cationic di-esters of the formula R'COOCHa CH-CH_-NR;R,R, X-/
RSCOO

wherein R1, R. and R3 are each an alkyl or hydroxyalkyl group containing from 1 to 4 carbon atoms, or a benzyl group, R, and Rsare each alkyl chains containing from 11 to 23 carbon atoms and X- is a water soluble anion.

One of the problems associated with fabric softening compositions containing cationic di-esters as disclosed in US
4 137 180 is the physical instability of these compounds, the problem is exacerbated at temperatures above or below ambient.
EP 280 550 and EP 507 478 (Unilever) discloses the use of selected nonionic stabilising agents to overcome the poor stability. However we have found that many nonionic stabilising agents create a further problem in that their presence destroys the viscosity of these fabric softening compositions.

EP 409 504 (Unilever ) discloses fabric softening compositions comprising at least 1% w/w of an ester linked quat and an extruder material which can be esters of predominantly linear Ca-C28 fatty acids with polyhydric alcohols.

AMENDED SHSEi' - 2a -WO 95/27777 discloses rinse conditioners comprising a fabric softening compound and a solubilising agent to be coated onto a tufible dryer sheet.

We have now found that selected nonionic stabilising agents do not destroy the viscosity of fabric softening compositions containing a biodegradable quaternary ammonium material.
Description of the Invention Accordingly the present invention relates to a fabric softening composition comprising:

~-.

AMENDED SHEET

a) a water insoluble, quaternary ammonium material comprising one ester link and two C12_28 alkyl or alkenyl groups;

} 5 b) a nonionic stabilising agent;

characterised in that the nonionic stabilising agent is a sucrose ester or an alkyl polyglucoside.

Further disclosed is a process for making a liquid fabric softening composition comprising the steps of selecting the following ingredients:

a) a water insoluble, quaternary ammonium material having at least one ester link and two C12_28 alkyl or alkenyl groups;

b) a nonionic stabilising agent which is either a sucrose ester or an alkyl polyglucoside;
c) other optional ingredients;

mixing the ingredients whilst heating to form a melt, followed by dispersing the melt in hot water to give the rinse conditioner.

Detailed Describtion of the Invention The present invention is a way of controlling the viscosity of a fabric conditioner composition containing a biodegradable quaternary ammonium material and a nonionic stabilising agent. Suitable nonionic stabilising agents include the sucrose esters such as sucrose distearate and sucrose monostearate, and the alkyl polyglucosides such as stearyl monoglucosides and stearyl triglucoside.

Without wishing to bound by theory, this invention is thought to operate in that the interaction of the hydrogen bonding elements of the molecules of the nonionic stabilising agent are essential to maintain a vesicular structure. A vesicular structure in the context of this invention can be defined as a spherical structure having onion ring shaped bilayers. The presence of such vesicular structures are an important factor in the formation of a composition with a commercially acceptable viscosity.
The preferred level of nonionic stabilising agent present is 0.1 to 2.5 % by weight.

Most preferred nonionic stabilising agents are the sucrose esters. The sucrose esters have the additional benefit that they impart additional softening benefits over the cationic softening agent. Examples of suitable sucrose esters include the Crodesta (Trademark (ex Croda)) series. Crodestas are sucrose esters esterified with 70/30 mixture of stearic/palmitic acid to form a mixes of mono-ester, di-ester and triester. According to.the manufacturer the levels of mono-ester are as follows:

Trade Name wt % monoester Crodesta F10 3 Crodesta F20 10 Crodesta F50 29 Crodesta F70 56 Crodesta F110 52 Crodesta F140 57 Crodesta F160 - 75 We have found that these combination of mono-esters and di-esters and triesters of sucrose give particularly good softening benefits. Especially preferred are combinations of mono-ester, di-ester and triester that contain 56-75%
monoester, in particular Crodesta F160, Crodesta F140, Crodesta 110 and Crodesta F70.

The fabric softening compound is suitably a substantially water insoluble quaternary ammonium material comprising a polar head group and two alkyl or alkenyl chains each having an average chain length greater than or equal to C14, and at least one ester group.

Preferably the fabric softening compound of the invention has two long chain alkyl or alkenyl chains, each having an average chain length greater than or equal to C16. Most preferably at least 50% of each long chain alkyl or alkenyl group has a chain of C.

It is preferred if the long chain alkyl or alkenyl groups of the fabric softening compound are predominantly linear.

The fabric softening compounds used in the compositions of the invention are molecules which provide excellent softening, and characterised by a chain melting -LP to LOG -transition temperature greater than 25 C, preferably greater than 35 C, most preferably greater than 45 C. This Lp to La transition can be measured by DSC as defined in "Handbook of ti Lipod Bilayers, D Marsh, CRS Press, Boca Raton Florida, 1990 (Pages 137 and 337).

Substantially insoluble fabric softening compounds in the context of this invention are defined as fabric softening compounds having a solubility less than 1 x 10-3 wt% in demineralised water at 20 C. Preferably the fabric softening compounds have a solubility less than 1 x 10-4. Most preferably the fabric softening compounds have a solubility at 20 C in demineralised water from 1 x 10-8 to 1 x 10'6.
It is especially preferred if the fabric softening compound is a water insoluble quaternary ammonium material which comprises a compound having two C1._la alkyl or alkenyl groups connected to the molecule via at least one ester link. It is more preferred if the quaternary ammonium material has two ester links present. An especially preferred ester-linked quaternary ammonium material for use in the invention can be represented by the formula:

R' I
R' = N' (CH,) n-T-R2 X' I
(CH; ) ,,-T-R' wherein each R1 group is independently selected from C1_4 alkyl, hydroxyalkyl or C1_, alkenyl groups; and wherein each R= group is independently selected from C$_a8 alkyl or alkenyl groups; X- is any suitable anion. 35 T is -O-C- or -C-O-; and n is an integer from 0-5.
Di(tallowyloxyethyl) dimethyl ammonium chloride is especially preferred.

A second preferred type of quaternary ammonium material can be represented by the formula OOCR' ( R1) 3N' - (CH2 ) n CH X-wherein R1, X-, n and R 2 are as defined above.

Preferred materials of this class such as 1,2 bis[hardened tallowoyloxy]-3- trimethylammonium propane chloride and their method of preparation are, for example, described in US 4 137 180 (Lever Brothers). Preferably 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.
It is preferred if the quaternary ammonium compound is biodegradable. Biodegradable in the context of this invention should be interpreted as meaning degrades to materials that are not known to be harmful to the environment.

The ratio of quaternary ammonium material to nonionic stabilising agent is in the range from 5:0.5 to 5:0.1.
The composition may also contain long chain fatty acid material for example C8 - Caq alkyl or alkenyl monocarboxylic acids or polymers thereof. Preferably saturated fatty acids are used, in particular hardened tallow C16 - C18 fatty acids.
Preferably the fatty acid is non-saponified, more preferably the fatty acid is free for example oleic acid. lauric acid or tallow fatty acid.

The level of fatty acid material is preferably more than 0.1%, more preferably more than 0.2% by weight. Especially preferred are dilutes in which the fatty acid material is present from 0.25 wt% to 20 wt%. The weight ratio of quaternary ammonium compound to fatty acid material is preferably from 1:10 to 10:1.

It is desirable if the viscosities of these fabric compositions lie in the range from 15 mPa.s to 120 mPa.s at a shear rate of 110s-1.

The compositions of the invention preferably have a pH of more than 2, more preferably between 2 and S.
The composition-can also contain one or more optional ingredients, selected from the group consisting of non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colorants, hydrotopes, antifoaming agents, antiredeposition agents, enzymes, optical brighteners, opacifiers, antishrinking agents, drape imparting agents, antistatic agents and ironing aids.

The composition may also contain nonionic fabric softening agents such as lanolin and derivatives thereof.

The invention will now be illustrated by the following non-limiting examples.

EXAMPLES

in the examples all percentages are expressed by weight.
Comparative examples are represented by a letter while examples of the invention are represented by a number.

In the Examples HEQ is 1,2 bis[hardened tallowoyloxy]-3-trimethylammonium propane chloride ex Hoechst.

Preparation of Fa]2ric Conditionina Composition Liquid fabric softening agents were made up as follows:

The cationic fabric softening agent and/or fatty acid and/or nonionic stabilising agent where appropriate were premixed and heated together to form a clear melt. The molten mixture thus formed was added over a period of at least one minute to water at 70 C to 80 C with constant stirring to form a dispersion.

_ ~ .

S (i g Co_a ity.Mansr P~ t s Viscosity was measured using the Haakem RV20 Rotov.i3cometer.
Viscosity is quoted ac a shear rate of 10s''. The Casson data are obtained by using the Casson relationship:

T0.5_T0 D0.3 Where:

= Shear Stress (Pa) TQ
= Yield Stress (Pa) = infinite shear rate viscosity (raPa.s) D
= Shear rate (s'' ) The Casson data were generated using the Haake RV20 Rotoviscometer with a range of shear rates from 0-1000s''.
F-xam,,.n1 _2 Conibaratiye Examolga A-D

Compositions were prepared in which an aqueous dispersion of 5t 6:1 HEQ:fatty acid, 0.5% of the following nonionics were added:

~

- IZ -T bel Example Nonionic A No nonionic B Genapol" T-150 C Tween" 80 D Tween 85 1 Crodesta F50 2 Crodesta F110 Genapol, Tween and Crodesta are trade marks.

The effect of nonionic type on viscosity of a dilute quaternary ammonium compound is shown in Table 2.

Table 2 Example 1i,o (mPa . s) (1I.(mpa.g) ICcament.
A 66 14.2 Vesicular B 26 4.6 No vesicles C 15 5.4 No vesicles D 16 8.4 No vesicles 1 87 22.0 Vesicles 2 48 12.3 Vesicles It can be seen that in the absence of nonionic the composition has a vesicular structure and accordingly has an acceptable viscosity. However the presence of nonionics stabilising agents which are not as specified by this invention, such as Genapol T-150, Tween 80 and 'I*ween 85, do not allow vesicle formation and hence the viscosity of the composition is unacceptably low. The examples according to the invention allow vesicle formation and so have an acceptably high viscosity.

Co=arat i ve Examnl .s E-G

Compositions were prepared in which 0.5% of the following nonionic were placed in a composition containing an aqueous dispersion of 5% 6:1 dihardened tallow dimethyl ammonium chloride:fatty acid.

Example E No nonionic Example F Genapol T-150 Example G Crodesta F50 The results are shown in Table 3.
Table 3 Example T1110(mPa.s) Tl..(mPa.s) Comments E 184 21.8 Vesicular F 238 10.9 Vesicular G --- ---- Vesicular Table 3 demonstrates that nonionic stabilising agents do not destroy the viscosity in formulations containing dihardened tallow dimethyl ammonium chloride.
Examnles 3-10 Comoarative Exambles A-B

To a base formulation of 5% HEQ:Hardened tallow fatty acid 6:1 in water the following nonionic stabilising agents were added:

= Example 3 0.25 % Crodesta F160 Example 4 0.50 % Crodesta F160 Example 5 0.50 % Crodesta F10 Example 6 0.50 % Crodesta F20 Example 7 0.50 % Crodesta F50 Example 8 0.50% Crodesta F70 Example 9 0.50% Crodesta F110 Example 10 0.50 % Crodesta F160 The softening performance of the sugar esters are demonstrated by Table 4.

Table 4 Examples SScore Total Votes 3 0.8828 31 4 1.0750 37 A 0.0000 6 B 0.5862 22 95% significance is obtained with a difference (A) between products of 0.9041. 90% significance is obtained when A=0.7565. it is thus demonstrated that the sucrose esters exhibit a significant softening benefit.
Table 5 demonstrates the optimum level of mono-ester present to maximise the softening effect.

Table 5 ' F.2rsLm2jo Softenina Score yotes 0.0000 17 6 0.1689 25 7 0.2136 27 8 0.9444 54 9 1.3931 71 10 0.7005 46

Claims (8)

Claims:
1) An aqueous fabric softening composition comprising:
a) a water insoluble, quaternary ammonium material comprising at least one ester link and two C22-28 alkyl or alkenyl groups;

b) a nonionic stablilizing agent;

characterised in that the nonionic stabilizing agent is a mixture of a mono-ester, a di-ester and a tri-ester sucrose ester and in that the composition comprises an aqueous dispersion of the water insoluble quaternary ammonium material
2) A fabric softening composition according to Claim 1 in which the nonionic stabilising agent comprises from 56 wt% to 75 wt% of sucrose mono-ester.
3) A fabric softening composition according to Claim 1 or 2 in which the level of nonionic stabilising agent is from 0.1 wt% to 2.5 wt% of the total composition.
4) A fabric softening composition according to Claims 1, 2 or 3 in which the ratio of quaternary ammonium material to nonionic stabilising agent is in the range from 5:0.5 to 5:0.1.
5) A fabric softening composition according to any one of Claims 1 to 4 in which the viscosity of the composition is in the range from 15mPa.s to 120mPa.s at a shear rate of 110s-1.
6) A fabric softening composition according to any one of Claims 1 to 5 in which the composition further comprises more than 0.1 wt% of a fatty acid material.
7) A fabric softening composition according to claim 6 in which the fatty acid material is present from 0.25 wt% to 20 wt%.
8) A process for making a liquid fabric softening composition comprising the steps of selecting the following ingredients:

a) a water insoluble, quaternary ammonium material comprising at least one ester link and two C12-28 alkyl groups;

b) a nonionic stabilising agent which is a sucrose ester;

then mixing the ingredients whilst heating to form a melt, followed by dispersing the melt in water, to form an aqueous dispersion of the water insoluble quaternary ammonium material.
CA002233229A 1995-10-23 1996-09-25 Fabric softening composition Expired - Fee Related CA2233229C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9521667.7 1995-10-23
GBGB9521667.7A GB9521667D0 (en) 1995-10-23 1995-10-23 Fabric softening composition
PCT/EP1996/004260 WO1997015651A1 (en) 1995-10-23 1996-09-25 Fabric softening composition

Publications (2)

Publication Number Publication Date
CA2233229A1 CA2233229A1 (en) 1997-05-01
CA2233229C true CA2233229C (en) 2008-04-22

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA002233229A Expired - Fee Related CA2233229C (en) 1995-10-23 1996-09-25 Fabric softening composition

Country Status (9)

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EP (2) EP1179582B1 (en)
AU (1) AU7216696A (en)
BR (1) BR9611214A (en)
CA (1) CA2233229C (en)
DE (2) DE69637748D1 (en)
ES (2) ES2316412T3 (en)
GB (1) GB9521667D0 (en)
WO (1) WO1997015651A1 (en)
ZA (1) ZA968475B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6017832A (en) * 1996-09-04 2000-01-25 Kimberly-Clark Worldwide, Inc. Method and composition for treating substrates for wettability
US6028016A (en) * 1996-09-04 2000-02-22 Kimberly-Clark Worldwide, Inc. Nonwoven Fabric Substrates Having a Durable Treatment
GB9930105D0 (en) * 1999-12-20 2000-02-09 Unilever Plc Fabric softening compounds and compositions
GB9930433D0 (en) * 1999-12-22 2000-02-16 Unilever Plc Use of fabric conditioning compositions for ironing benefits
US7776813B2 (en) 2004-09-15 2010-08-17 The Procter & Gamble Company Fabric care compositions comprising polyol based fabric care materials and deposition agents
GB0501006D0 (en) * 2005-01-18 2005-02-23 Unilever Plc Fabric conditioning compositions
BRPI0914903A2 (en) 2008-06-05 2015-10-20 Unilever Nv Use of a sucrose polyester to reduce unwanted odors in fabric conditioners

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1617115A1 (en) * 1966-06-04 1971-02-18 Henkel & Cie Gmbh Active agent concentrates for cleaning rigid material
GB8916307D0 (en) * 1989-07-17 1989-08-31 Unilever Plc Fabric softening composition
GB9209170D0 (en) * 1992-04-28 1992-06-10 Unilever Plc Rinse conditioner
GB9406824D0 (en) * 1994-04-07 1994-06-01 Unilever Plc Fabric softening composition
DE69618969T2 (en) * 1995-08-31 2002-09-19 Colgate Palmolive Co STABLE SOFTENER COMPOSITIONS
GB9520519D0 (en) * 1995-10-04 1995-12-13 Unilever Plc Detergent composition

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Publication number Publication date
EP0877786A1 (en) 1998-11-18
AU7216696A (en) 1997-05-15
ES2185804T3 (en) 2003-05-01
EP0877786B1 (en) 2002-12-04
GB9521667D0 (en) 1996-01-03
DE69625243D1 (en) 2003-01-16
DE69625243T2 (en) 2003-04-17
DE69637748D1 (en) 2008-12-24
CA2233229A1 (en) 1997-05-01
ZA968475B (en) 1998-04-08
BR9611214A (en) 1999-04-06
EP1179582A3 (en) 2003-07-16
ES2316412T3 (en) 2009-04-16
EP1179582A2 (en) 2002-02-13
WO1997015651A1 (en) 1997-05-01
EP1179582B1 (en) 2008-11-12

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