WO2025201755A1

WO2025201755A1 - Laundry composition

Info

Publication number: WO2025201755A1
Application number: PCT/EP2025/054536
Authority: WO
Inventors: Matthew Charles HERBISON; Daniel Mcmahon; Kallum MISTRY
Original assignee: Unilever Global IP Ltd; Unilever IP Holdings BV; Conopco Inc
Current assignee: Unilever Global IP Ltd; Unilever IP Holdings BV; Conopco Inc
Priority date: 2024-03-28
Filing date: 2025-02-20
Publication date: 2025-10-02
Anticipated expiration: 2026-09-28

Abstract

The present invention relates to fabric conditioner compositions. Fabric conditioner compositions deliver softening and a fragrance to fabrics in the rinse stage of the laundry process. Fragrance is an important aspect of the laundry process, consumers desire that laundered fabrics smell nice, indicating that they are clean. It has been found that the inclusion of a glucamide surfactant increases the amount of perfume in the headspace above wet fabric.

Description

LAUNDRY COMPOSITION

Field of the Invention

The present invention relates to fabric conditioner compositions.

Background of the Invention

Fabric conditioner compositions deliver softening and a fragrance to fabrics in the rinse stage of the laundry process. Fragrance is an important aspect of the laundry process, consumers desire that laundered fabrics smell nice, indicating that they are clean. A particularly important stage for fragrance performance is the headspace above wet fabrics. When consumers remove their wet fabrics from a washing machine to hang up or move to a tumble drier, the presence of fragrance demonstrates to the consumer that the clothes are clean. Therefore, there is a desire to enhance the headspace above wet fabrics.

Summary of the Invention

It has been found that the inclusion of a glucamide surfactant increases the amount of perfume in the headspace above wet fabric.

Accordingly in a first aspect of the present invention is provided a fabric conditioner composition comprising: a. 1 to 30 wt.% ester-linked quaternary ammonium compound; b. 0.05 to 6 wt.% glucamide surfactant; and c. 0.1 to 20 wt.% perfume.

Additionally, the present invention provides a method of enhancing the consumer fragrance experience on wet fabric, wherein a fabric conditioner as described herein is delivered to the fabric in the rinse stage of the laundry process.

In a further aspect is provided a use of a fabric conditioner as described herein to enhance the consumer fragrance experience, preferably the experience when handling wet fabric, wherein a composition as described herein is delivered to the fabric in the rinse stage of the laundry process. Detailed Description of the Invention

These and other aspects, features and advantages will become apparent to those of ordinary skill in the art from a reading of the following detailed description and the appended claims. For the avoidance of doubt, any feature of one aspect of the present invention may be utilised in any other aspect of the invention. The word “comprising” is intended to mean “including” but not necessarily “consisting of” or “composed of.” In other words, the listed steps or options need not be exhaustive. It is noted that the examples given in the description below are intended to clarify the invention and are not intended to limit the invention to those examples per se. Similarly, all percentages are weight/weight percentages unless otherwise indicated. Except in the operating and comparative examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material or conditions of reaction, physical properties of materials and/or use are to be understood as modified by the word “about”. Numerical ranges expressed in the format "from x to y" are understood to include x and y. When for a specific feature multiple preferred ranges are described in the format "from x to y", it is understood that all ranges combining the different endpoints are also contemplated.

The compositions described herein comprise 1 to 30 wt.% ester-linked quaternary ammonium compound. Preferably the compositions comprise 1.5 to 20 wt.% ester-linked quaternary ammonium compound, most preferably 2 to 15 wt.% ester-linked quaternary ammonium compound by weight of the composition.

The ester linked quaternary ammonium compound preferably comprises at least one chain derived from fatty acids, more preferably at least two chains derived from a fatty acid. Preferably the fatty acids are defined as aliphatic monocarboxylic acids having a chain of 4 to 28 carbons. Fatty acids may be derived from various sources such as tallow or plant sources (e.g. palm oil). Preferably the fatty acid chains are derived from plants. Preferably the fatty acid chains of the ester linked quaternary ammonium compound comprise from 10 to 50 wt. % of saturated C18 chains and from 5 to 40 wt. % of monounsaturated C18 chains by weight of total fatty acid chains. In a further preferred embodiment, the fatty acid chains of the ester linked quaternary ammonium compound comprise from 20 to 40 wt. %, preferably from 25 to 35 wt. % of saturated C18 chains and from 10 to 35 wt. %, preferably from 15 to 30 wt. % of monounsaturated C18 chains, by weight of total fatty acid chains.

Particularly preferred materials are ester-linked triethanolamine (TEA) quaternary ammonium compounds comprising a mixture of mono-, di- and tri-ester linked components. A first group of ester linked quaternary ammonium compounds suitable for use in compositions described herein are represented by formula (I): wherein each R is independently selected from a C5 to C35 alkyl or alkenyl group; R¹ represents a C1 to C4 alkyl, C2 to C4 alkenyl or a C1 to C4 hydroxyalkyl group; T may be either O-CO. (i.e. an ester group bound to R via its carbon atom), or may alternatively be CO-O (i.e. an ester group bound to R via its oxygen atom); n is a number selected from 1 to 4; m is a number selected from 1, 2, or 3; and X- is an anionic counter-ion, such as a halide or alkyl sulphate, e.g. chloride or methylsulfate. Di-esters variants of formula I (i.e., m = 2) are preferred and typically have mono- and tri-ester analogues associated with them. Such materials are particularly suitable for use in the present invention.

A second group of ester linked quaternary ammonium compounds suitable for use in the compositions described herein are represented by formula (II):

(R^NHCH -CH-TR^ X- (II) wherein each R¹ group is independently selected from C1 to C4 alkyl, hydroxyalkyl or C2 to C4 alkenyl groups; and wherein each R² group is independently selected from C8 to C28 alkyl or alkenyl groups; and wherein n, T, and X- are as defined above.

Preferred materials of this second group include 1,2 bis[tallowoyloxy]-3- trimethylammonium propane chloride, 1 ,2 bis[hardened tallowoyloxy]-3- trimethylammonium propane chloride, 1 ,2- bis[oleoyloxy]-3-trimethylammonium propane chloride, and 1,2 bis[stearoyloxy]-3- trimethylammonium propane chloride. Such materials are described in US 4, 137,180 (Lever Brothers). Preferably, these materials also comprise an amount of the corresponding monoester.

A third group of ester linked quaternary ammonium compounds suitable for use in the compositions described herein are represented by formula (III): (R' -N'-[(CH _r’T-R'l. X' (III) wherein each R¹ group is independently selected from C1 to C4 alkyl, or C2 to C4 alkenyl groups; and wherein each R² group is independently selected from C8 to C28 alkyl or alkenyl groups; and n, T, and X- are as defined above. Preferred materials of this third group include bis(2-tallowoyloxyethyl)dimethyl ammonium chloride, partially hardened and hardened versions thereof.

A fourth group of ester linked quaternary ammonium compounds are represented the by the formula (IV):

A fifth group of ester linked quaternary ammonium compounds suitable for use in the invention are represented by formula (V)

Ri and R2 are independently selected from C10 to C22 alkyl or alkenyl groups, preferably C14 to C20 alkyl or alkenyl groups. X- is as defined above.

A sixth group of ester linked quaternary ammonium compounds suitable for use in the present compositions are compounds obtained by reacting: i) a mixture of at least one dicarboxylic acid of formula (VI)

Formula (VI) wherein X represents a saturated or unsaturated hydrocarbon residue having 1 to 8 carbon atoms, and at least one monocarboxylic acid of formula (VII) Formula (VII) wherein R1 represents a saturated or unsaturated hydrocarbon residue having 5 to 21 carbon atoms, with ii) at least one tertiary amine of formula (VIII) Formula (VIII) wherein R², R³, and R⁴ independently represent a C2 to Ce hydroxyalkyl group, preferably 2-hydroxyethyl, and then reacting the resulting product with iii) at least one quaternizing agent for quaternizing at least one amino group contained in the reaction product.

In the dicarboxylic acid of formula (VI), X preferably represents a group having 2 to 8 carbons, X preferably represents a hydroxy-substituted linear or branched alkyl or alkylene. More preferably, X represents ethan-1 ,2-diyl, propan-1 , 2-diyl, propan-1 , 3-diyl, butan-1 ,4-diyl, hexan- 1 ,4-diyl, or cyclohexan-1 ,4-diyl, particularly preferably X represents butan-1 , 4-diyl. Even more preferably the dicarboxylic acid is selected from: succinic acid, maleic acid, glutaric acid, adipic acid and combinations thereof. Most preferably the dicarboxylic acid comprises adipic acid.

In the monocarboxylic acids of formula (VII), R1CO preferably represents an aliphatic, linear, or branched acyl residue having 6 to 22 carbon atoms. Preferably the monocarboxylic acid is selected from caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, 2-octyldodecanoic acid, eleostearic acid, arachidic acid, gadoleic acid, behenic acid, erucic acid, coconut fatty acid, palm fatty acid, palm kernel fatty acid, tallow fatty acid and combinations thereof. Industrial mixtures thereof which are produced, for example, during the pressurized cleavage of natural fats and oils, during the reduction of aldehydes from the Roelen oxo synthesis, or the dimerization of unsaturated fatty acids may also be used. More preferably the monocarboxylic acid is selected from: Stearic acid, isostearic acid, palmitic acid, myristic acid, lauric acid, capric acid, caprylic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, caproic acid, oleic acid, linoleic acid, and linolenic acid, coconut fatty acid, palm fatty acid, palm kernel fatty acid, tallow fatty acid and combinations thereof.

Preferably the dicarboxylic acid of formula (VI) is selected from: succinic acid, maleic acid, glutaric acid, adipic acid, and combinations thereof and the monocarboxylic acid of formula (II) is selected from: stearic acid, isostearic acid, palmitic acid, myristic acid, lauric acid, capric acid, caprylic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, caproic acid, oleic acid, linoleic acid, linolenic acid, partially-hydrogenated coconut fatty acid, palm fatty acid, palm kernel fatty acid, tallow fatty acid and combinations thereof.

The alkanolamines of formula (VIII), preferably contain a hydroxyalkane residue (alkanol residue) having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. Preferably the alkanolamines of formula (III) comprises triethanolamine.

The monocarboxylic acids (of formula VII) and the dicarboxylic acids (of formula VI) may be used in the molar ratio of from about 1 :10 to about 10:1. It has, however, proven advantageous to use a molar ratio of from about 1 :1 to about 4:1 and, in particular, from about 1.5:1 to about 3:1.

In an especially preferred embodiment of the sixth type of ester linked quaternary ammonium compounds, is an esterquat compound of formula (IX) wherein,

X is a saturated or unsaturated hydrocarbon residue having 1 to 10 carbon atoms preferably butan-1 ,4-diyl

A is a (C2 to C6) alkanediyl group, preferably ethan-1 ,2-diyl

R1 is a (C2 to C4) hydroxyalkyl group or a (C6 to C22) acyloxy (C2 to C4) alkyl group, preferably 2-hydroxyethyl or 2-((C6 to C22) acyloxy)ethyl;

R2 is methyl or ethyl;

R3 and R4-independently are a hydrogen atom or a (C6 to C2) acyl group; n is 1 or 2; and

Z- is an anion, preferably methyl sulphate;

And wherein, at least one of the groups R1 , R3, or R4 comprises a (C6 to C22) acyl residue.

The compositions defined herein comprise 0.05 to 6 wt.% glucamide surfactant. The compositions preferably comprise 0.1 to 4 wt.%, more preferably 0.15 to 2 wt.% glucamide by weight of the composition.

Glucamide surfactants are non- ionic surfactants in which the hydrophilic moiety (an aminosugar derivative) and the hydrophobic moiety (a fatty acid) are linked via amide bonds.

Preferred glucamides are alkyl glucamide surfactant. More preferred alkyl glucamide surfactants are N-alkyl-N-acylglucamides of the formula (X):

Ra is a linear or branched, preferably linear,

Ra is saturated or unsaturated, preferably unsaturated, more preferably monounsatureated, Ra is a hydrocarbyl group having 6 to 22 carbon atoms, more preferably 10 to 20, most preferably 16 to 18 carbon atoms.

In a particularly preferred embodiment Ra is a linear, monounsaturated 16 to 18 carbon.

Rb is a linear or branched alkyl group or an aryl group, preferably a linear alkyl group comprising 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, most preferably Rb is a methyl group.

Preferably the molecular weight of the glucamide surfactant is 1000g/mol or less, more preferably 900g/mol or less and most preferably 800g/mol or less.

Non-limiting examples of glucamide surfactants are: N-octanoyl-N- methylglucamide, N- nonanoyl-N-methylglucamide, N-decanoyl-N-methylglucamide, N- dodecanoyl-N- methylglucamide, N-cocoyl-N-methylglucamide, (available under the trade name of GlucoPure Foam by from Clariant), N-lauroyl/myristoyl-N-methylglucamide, (available under the trade name of GlucoPure Deg by from Clariant), and N-octanoyl/decanoyl-N- methylglucaminemethylglucamide, (available under the trade name of GlucoPure Wet by Clariant).

The compositions described herein comprise 0.1 to 20 wt.% perfume. Preferably the compositions comprise 0.5 to 15 wt.% perfume and most preferably 1 to 10 wt.% perfume.

Perfume is considered to be any non-encapsulated perfume in the composition.

Particularly preferred perfume components are blooming perfume components and substantive perfume components. Blooming perfume components are defined by a boiling point less than 250°C and a LogP or greater than 2.5. Substantive perfume components are defined by a boiling point greater than 250°C and a LogP greater than 2.5. Boiling point is measured at standard pressure (760 mm Hg). Preferably a perfume composition will comprise a mixture of blooming and substantive perfume components. The perfume composition may comprise other perfume components.

It is commonplace for a plurality of perfume components to be present in a free oil perfume composition. In the compositions for use in the present invention it is envisaged that there will be three or more, preferably four or more, more preferably five or more, most preferably six or more different perfume components. An upper limit of 300 perfume components may be applied.

Preferably the perfume comprises at least one ingredient selected from: Aldehyde C12 MNA, verdyl acetate, cyclamen aldehyde, beta ionone, hexyl salicylate, tonalid, and combinations thereof. These ingredients show a particular benefit on wet fabrics.

In addition to the perfume, the compositions may comprise perfume microcapsules, in other words encapsulated perfume. The encapsulating materials, preferably comprise, but are not limited to; aminoplasts, proteins, polyvinyl acetates, polyurethanes, polyacrylates, polymethacrylates, polysaccharides, polyamides, polyolefins, gums, silicones, lipids, modified cellulose, polyphosphate, polystyrene, polyesters or combinations thereof. More preferably the encapsulating materials comprise polyvinyl acetate, proteins, polysaccharides or combinations thereof. The compositions described herein may comprise further ingredients suitable for use in fabric conditioners and known to the person skilled in the art. A non-limiting list of such ingredients include: additional non-ionic surfactants (in addition to the glucamide), fatty acids, fatty esters, solvents, antifoams, anti-malodour ingredients, insect repellents, shading or hueing dyes, preservatives (e.g. bactericides), pH buffering agents, perfume carriers, hydrotropes, antiredeposition agents, soil-release agents, dye transfer inhibitors, polyelectrolytes, anti-shrinking agents, anti-wrinkle agents, anti-oxidants, dyes, colorants, sunscreens, anti-corrosion agents, drape imparting agents, anti-static agents, oils (e.g. plant based oils and mineral oils), plant extracts, waxes, sugar-esters, silicones, sequestrants, ironing aids, pearlisers or opacifiers.

The fabric conditioner composition is preferably in an aqueous form. The compositions preferably comprise at least 75 wt.% water. The compositions may be opaque, translucent, or transparent.

The fabric conditioner compositions are preferably used in the rinse stage of the laundry cycle. The laundry cycle or laundry process may be machine washing or hand washing.

In one embodiment is provided a method of enhancing the consumer fragrance experience on wet fabric, wherein a fabric conditioner as described herein is delivered to the fabric in the rinse stage of the laundry process.

In a further embodiment is provided a use of the composition as described herein to enhance the consumer fragrance experience, preferably the experience when handling wet fabric, wherein a composition as described herein is delivered to the fabric in the rinse stage of the laundry process.

Examples

Table 1: Compositions

Ester linked quaternary ammonium compound¹ - according to formula (I)

Glucamide² - according to formula (X)

The compositions were prepared by the following method: the water heated to a temperature of ~38°C, minors were then added, followed by glucamide (were present). The fabric softening active was heated to ~ 65°C and added into the solution. The mixture was then cooled to ~37°C and the perfume oil and perfume microcapsules were then added. The mixture was then cooled to room temperature.

The samples were washed using a Ell front loading washing machine. 50g of unperfumed detergent powder was used in a 30°C was cycle. 30 ml of the test fabric conditioner composition was added in the rinse. The wash contained cotton samples, polyester samples and a mixed ballast.

The headspace benefit was analysed using VOC (volatile organic compound) headspace analysis with SPME-GC-MS. Wet fabrics were removed from the washing machine and a headspace sample obtained for measurement. The fragrance in the headspace was sampled using SPME and run using a Shimadzu QP2010 plus GC/MS instrument. Each sample was measured in triplicate. Table 2: results

Compositions comprising glucamide have increased perfume in the headspace above wet fabrics.

Claims

1. A fabric conditioner composition comprising: a. 1 to 30 wt.% ester-linked quaternary ammonium compound; b. 0.05 to 6 wt.% glucamide surfactant; and c. 0.1 to 20 wt.% perfume.

2. A composition according to claim 1, wherein the glucamide surfactant is an alkyl glucamide surfactant.

3. A composition according to any preceding claim, wherein the glucamide surfactant is a N- alkyl-N-acylglucamides of the formula (X):

Wherein Ra is linear or branched, saturated or unsaturated, comprising 6 to 22 carbon atoms; and

Rb is a linear or branched alkyl group or an aryl group

4. A composition according to claim 3, wherein Ra is linear.

5. A composition according to claim 3, wherein Ra is unsaturated.

6. A composition according to claim 3, wherein Ra comprises 10 to 20 carbon atoms.

7. A composition according to claim 3, wherein Ra is a linear, monounsaturated 16 to 18 carbon.

8. A composition according to claim 3, wherein Rb is a linear alkyl group comprising 1 to 6 carbon atoms.

9. A composition according to claim 3, wherein the glucamide surfactant has a molecular weight of 1000g/mol or less.

10. A method of enhancing the consumer fragrance experience on wet fabric, wherein a fabric conditioner according to any preceding claim is delivered to the fabric in the rinse stage of the laundry process.

11. A use of a fabric conditioner according to any preceding claim to enhance the consumer fragrance experience, preferably the experience when handling wet fabric, wherein a composition as described herein is delivered to the fabric in the rinse stage of the laundry process.