EP1794274A1 - Laundry treatment compositions - Google Patents

Laundry treatment compositions

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Publication number
EP1794274A1
EP1794274A1 EP05771350A EP05771350A EP1794274A1 EP 1794274 A1 EP1794274 A1 EP 1794274A1 EP 05771350 A EP05771350 A EP 05771350A EP 05771350 A EP05771350 A EP 05771350A EP 1794274 A1 EP1794274 A1 EP 1794274A1
Authority
EP
European Patent Office
Prior art keywords
group
laundry treatment
treatment composition
hydrolysed
reactive
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP05771350A
Other languages
German (de)
French (fr)
Other versions
EP1794274B1 (en
EP1794274B2 (en
Inventor
Stephen N. Unilever R & D Port Sunlight BATCHELOR
Jayne Michelle Unilever R & D Port Sunlight BIRD
John Unilever R & D Port Sunlight LLOYD
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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Application filed by Unilever PLC, Unilever NV filed Critical Unilever PLC
Publication of EP1794274A1 publication Critical patent/EP1794274A1/en
Publication of EP1794274B1 publication Critical patent/EP1794274B1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments

Abstract

The present invention provides a laundry treatment composition comprising a surfactant and a hydrolysed reactive dye. A method of treating the textile, comprising treating the textile with an aqueous solution of the hydrolysed dye, rinsing and drying the textile, is also claimed.

Description

LAUNDRY TREATMENT COMPOSITIONS
TECHNICAL FIELD
The present invention relates to laundry treatment compositions which comprise a dye.
BACKGROUND OF THE INVENTION
Reactive dyes are coloured compounds with one or more functional groups capable of forming a covalent bond with a suitable substrate, generally cotton or other cellulosic fibres. Typical reactive groups of the reactive dyes are monochlorotriazinyl, monofluorotrazinyl and 2- sulfooxyethylsulfonyl. Typical chromophores of the reactive dyes are azo, anthraquinone, phthalocyanine, formazan and triphendioaxazine.
The reactive dyes have specific functional groups that can undergo addition or substitution reactions with -OH, -SH and -NH2 groups present in textile fibers. A consequence of the nature of these specific functional groups is that reactive dyes can cause irritation/sensitization of the respiratory tract and skin. There is also evidence that they give rise to contact dermatitis, allergic conjunctivis, rhinitis, occupational asthma and other allergic reactions.
SUMMARY OF THE INVENTION
We have found that hydrolysed reactive dyes may be used to impart shading to textiles whilst reducing the risk of irritation/sensitization of the respiratory tract and skin in comparison to reactive dyes. In the presence of water and high pH the reactive groups of reactive dyes are hydrolysed. We have found that the hydrolysed reactive dye is also substantive to cotton under normal wash conditions.
In one aspect the present invention provides a laundry treatment composition comprising between 0.0001 to 0.1 wt % of a hydrolysed reactive dye and between 2 to 60 wt % of a surfactant.
In another aspect the present invention provides a method of treating a textile, the method comprising the steps of: (i) treating a textile with an aqueous solution of a hydrolysed reactive dye, the aqueous solution comprising from 10 ppb to 1 ppm of the hydrolysed reactive dye and from 0.2 g/L to 3 g/L of a surfactant;- and, (ii) rinsing and drying the textile. Most preferably the hydrolysed reactive dye is at a concentration in the range from 100 ppb to 500 ppb. The present invention also extends to the aqueous solution used in the method.
A "unit dose" as used herein is a particular amount of the laundry treatment composition used for a type of wash, conditioning or requisite treatment step. The unit dose may be in the form of a defined volume of powder, granules or tablet or unit dose detergent liquid.
DETAILED DESCRIPTION OF THE INVENTION
The reactive dyes may be considered to be made up of a chromophore which is linked to an anchoring moiety, The chromophore may be linked directly to the anchor or via a bridging group. The chromophore serves to provide a colour and the anchor to bind to a textile substrate.
A marked advantage of reactive dyes over direct dyes is that their chemical structure is much simpler, their absorption bands are narrower and the dyeing/shading are brighter; industrial Dyes, K. Hunger ed. Wiley-VCH 2003 ISBN 3-527- 30426-6. However, mammalian contact with reactive dyes results in irritation and/or sensitisation of the respiratory tract and/or skin. In addition, wash conditions are not ideal for deposition of dyes because the efficiency of deposition is low.
With regard to reducing irritation and/or sensitisation, it is preferred that each individual anchor group of each reactive dyes is hydrolysed such that the most reactive group (s) of anchor groups of the dye is/are hydrolysed. In this regard, the term hydrolysed reactive dye encompasses both fully and partially hydrolysed reactive dyes.
The reactive dye may have more than one anchor. If the dye has more than one anchor, then each and every anchor, that contributes to irritation and/or sensitisation, needs to be hydrolysed to the extent discussed above.
The dyes used in the present invention comprise a chromophore and an anchor that are covalenly bound and may be represented in the following manner: Chromophore-anchor. The linking between the chromophore and an anchor are preferably provided by -NH-CO-, -NH-, NHCO-CH2CH2-, -NH-CO-, or -N=N-. It is preferred that when a "unit dose" of the laundry treatment composition is dissolved in water the ionic strength of the resultant aqueous laundry treatment composition is between 0.001 to 0.5, more preferably between 0.02 to 0.2.
Preferably the hydrolysed reactive dye comprises a chromophore moiety covalently bound to an anchoring group, the anchoring group for binding to cotton, the anchoring group selected from the group consisting of: a heteroaromatic ring, preferably comprising a nitrogen heteroatom, having at least one -OH substituent covalently
-SO2-C-C-OH H2 H2 bound to the heteroaromatic ring, and
It is preferred that the anchor group is of the form:
wherein: n takes a value between 1 and 3;
X is selected from the group consisting of: -Cl, -F, NHR, a quaternary ammonium group, -OR and -OH; R is selected from: an aromatic group, benzyl, a C1-C6- alkyl; and, wherein at least one X is -OH. It is preferred that R is selected from napthyl, phenyl, and -CH3. Most preferably the anchor group is selected from the group consisting of:
SO5-C-C—OH H, H, and
Preferably, the chromophore is selected from the group consisting of: azo, anthraquinone, phthalocyanine, formazan and triphendioaxazine.
Preferably, the chromophore is linked to the hydrolysed anchor by a bridge selected from the group consisting of: - NH-CO-, -NH-, NHCO-CH2CH2-, -NH-CO-, and -N=N-.
Most preferred hydrolysed reactive dyes are hydrolysed Reactive Red 2, hydrolysed Reactive Blue 4, hydrolysed Reactive Black 5, and hydrolysed Reactive Blue 19.
BALANCE CARRIERS AND ADJUNCT INGREDIENTS The laundry treatment composition in addition to the hydrolysed reactive dye comprises the balance carriers and adjunct ingredients to 100 wt % of the composition.
These may be, for example, surfactants, builders, foam agents, anti-foam agents, solvents, fluorescers, bleaching agents, and enzymes. The use and amounts of these components are such that the composition performs depending upon economics, environmental factors and use of the composition.
The composition may comprise a surfactant and optionally other conventional detergent ingredients. The composition may also comprise an enzymatic detergent composition which comprises from 0.1 - 50 wt %, based on the total detergent composition, of one or more surfactants. This surfactant system may in turn comprise 0 - 95 wt % of one or more anionic surfactants and 5 to 100 wt % of one or more nonionic surfactants. The surfactant system may additionally contain amphoteric or zwitterionic detergent compounds, but this in not normally desired owing to their relatively high cost. The enzymatic detergent composition according to the invention will generally be used as 'a dilution in water of about 0.05 to 2 wt%.
It is preferred that the composition comprises between 2 to 60 wt % of a surfactant, most preferably 10 to 30 wt %. In general, the nonionic and anionic surfactants of the surfactant system may be chosen from the surfactants described "Surface Active Agents" Vol. 1, by Schwartz & Perry, Interscience 1949, Vol. 2 by Schwartz, Perry & Berch, Interscience 1958, in the current edition of "McCutcheon' s Emulsifiers and Detergents" published by Manufacturing Confectioners Company or in "Tenside-Taschenbuch", H. Stache, 2nd Edn., Carl Hauser Verlag, 1981.
Suitable nonionic detergent compounds which may be used include, in particular, the reaction products of compounds having a hydrophobic group and a -reactive hydrogen atom, for example, aliphatic alcohols, acids, amides or alkyl phenols with alkylene oxides, especially ethylene oxide either alone or with propylene oxide. Specific nonionic detergent compounds are C6-C22 alkyl phenol-ethylene oxide condensates, generally 5 to 25 EO, i.e. 5 to 25 units of ethylene oxide per molecule, and the condensation products of aliphatic C8- C18 primary or secondary linear or branched alcohols with ethylene oxide, generally 5 to 40 EO.
Suitable anionic detergent compounds which may be used are usually water-soluble alkali metal salts of organic sulphates and sulphonates having alkyl radicals containing from about 8 to about 22 carbon atoms, the term alkyl being used to include the alkyl portion of higher acyl radicals. Examples of suitable synthetic anionic detergent compounds are sodium and potassium alkyl sulphates, especially those obtained by sulphating higher Cs-Cis alcohols, produced for example from tallow or coconut oil, sodium and potassium alkyl C9-C20 benzene sulphonates, particularly sodium linear secondary alkyl C10-C15 benzene sulphonates; and sodium alkyl glyceryl ether sulphates, especially those ethers of the higher alcohols derived from tallow or coconut oil and synthetic alcohols derived from petroleum. The preferred anionic detergent compounds are sodium C11-C15 alkyl benzene sulphonates and sodium C12-C18 alkyl sulphates. Also applicable are surfactants such as those described in EP-A-328 177 (Unilever) , which show resistance to salting-out, the alkyl polyglycoside surfactants described in EP-A-070 074, and alkyl monoglycosides. Preferred surfactant systems are mixtures of anionic with nonionic detergent active materials, in particular the groups and examples, of anionic and nonionic surfactants pointed out in EP-A-346 995 (Unilever) . Especially preferred is surfactant system that is a mixture of an alkali metal salt of a C3.6-C18 primary alcohol sulphate together with a C12-C15 primary alcohol 3-7 EO ethoxylate.
The nonionic detergent is preferably present in amounts greater than 10%, e.g. 25-90 wt % of the surfactant system. Anionic surfactants can be present for example in amounts in the range from about 5% to about 40 wt % of the surfactant system.
CATIONIC COMPOUND
When the present invention is used as a fabric conditioner it needs to contain a cationic compound.
Most preferred are quaternary ammonium compounds.
It is advantageous if the quaternary ammonium compound is a quaternary ammonium compound having at least one C12-C22 alkyl chain.
It is preferred if the quaternary ammonium compound has the following formula:
in which R1 is a Ci2 to C22 alkyl or alkenyl chain; R2, R3 and R4 are independently selected from C1-C4 alkyl chains and X" is a compatible anion. A preferred compound of this type is the quaternary ammonium compound cetyl trimethyl quaternary ammonium bromide.
A second class of materials for use with the present invention are the quaternary ammonium of the above structure in which R1 and R2 are independently selected from C12 to C22 alkyl or alkenyl chain; R3 and R4 are independently selected from Ci-C4 alkyl chains and X~ is a compatible anion.
A detergent composition according to claim 1 in which the ratio of (ii) cationic material to (iv) anionic surfactant is at least 2:1.
Other suitable quatenary ammonium compounds are disclosed in EP 0 239 910 (Proctor and Gamble) .
It is preferred if the ratio of cationic to nonionic surfactant is from 1:100 to 50:50, more preferably 1:50 to 20:50.
The cationic compound may be present from 0.02 wt % to 20 wt % of the total weight of the composition.
Preferably the cationic compound may be present from 0.05 wt % to 15 wt %, a more preferred composition range is from 0.2 wt % to 5 wt %, and most preferably the composition range is from 0.4 wt % to 2.5 wt % of the total weight of the composition. If the product is a liquid it is preferred if the level of cationic surfactant is from 0.05wt % to 10wt % of the total weight of the composition. Preferably the cationic compound may be present from 0.2 wt % to 5 wt %, and most preferably from 0.4 wt % to 2.5 wt % of the total weight of the composition.
If the product is a solid it is preferred if the level of cationic surfactant is 0.05 wt % to 15 wt % of the total weight of the composition. A more preferred composition range is from 0.2 wt % to 10 wt %, and the most preferred composition range is from 0.9 wt % to 3.0 wt % of the total weight of the composition.
BLEACHING SPECIES
The laundry treatment composition may comprise bleaching species. The bleaching species, for example, may selected from perborate and percarbonate. These peroxyl species may be further enhanced by the use of an activator, for example, TAED or SNOBS. Alternatively or in addition to, a transition metal catalyst may used with the peroxyl species. A transition metal catalyst may also be used in the absence of peroxyl species where the bleaching is termed to be via atmospheric oxygen, see, for example WO02/48301. Photobleaches, including singlet oxygen photobleaches, may be used with the laundry treatment composition. A preferred photobleach is vitamin K.
FLUORESCENT AGENT The laundry treatment composition preferably comprises a fluorescent agent (optical brightener) . Fluorescent agents are well known and many such fluorescent agents are available commercially. Usually, these fluorescent agents are supplied and used in the form of their alkali metal salts, for example, the sodium salts. The total amount of the fluorescent agent or agents used in laundry treatment composition is generally from 0.005-2 wt %, more preferably 0.01 to 0.1 wt %. Preferred classes of fluorescer are: Di- styryl biphenyl compounds, e.g. Tinopal (Trade Mark) CBS-X, Di-amine stilbene di-sulphonic acid compounds, e.g. Tinopal DMS pure Xtra and Blankophor (Trade Mark) HRH, and
Pyrazoline compounds, e.g. Blankophor SN. Preferred fluorescers are: sodium 2 (4-styryl-3-sulfophenyl) -2H- napthol [1, 2-d]trazole, disodium 4, 4'-bis{ [ (4-anilino-β- (N methyl-N-2 hydroxyethyl) amino 1, 3, 5-triazin-2- yl) ] amino}stilbene-2-2 ' disulfonate, disodium 4, 4 ' -bis{ [ (4- anilino-6-morpholino-l, 3, 5-triazin-2-yl) ] amino} stilbene-2- 2' disulfonate, and disodium 4, 4 '-bis (2- sulfoslyryl)biphenyl.
EXAMPLES
Example 1: Deposition on cotton
To determine the substantivity of a dye the following experiment was performed. A 0.1 wt % solution of the reactive dye was created in a pH = 10 buffer and was left for four days in the dark at room temperature to allow the reactive groups to hydrolyse. A stock solution of 1.5 g/L of a base washing powder in water was created. The washing powder contained 18 % NaLAS, 73 % salts (silicate, sodium tri-poly-phosphate, sulphate, carbonate) , 3 % minors including perborate, fluorescer and enzymes, remainder impurities and water. The solution was divided into 60 ml aliquots and hydrolysed reactive dye added to this to give a solution of optical density of approximately one (5 cm pathlength) at the maximum absorption of the dye in the visible lengths, 400 to 700nm. The optical density was measured using a UV-visible spectrometer. One piece of bleached, non-mercerised, non-fluorscent woven non- mercerised cotton cloth (ex Phoenic Calico) weighing 1.3 g was placed in the solution at room temperature (20 0C) . This cloth represents a slightly yellow cotton. The cloth was left to soak for 45 minutes then the solution agitated for 10 min., rinsed and dried. Following this the optical density of the solution was re-measured and the amount of dye absorbed by the cloth calculated.
The results are given in the table below.
Reactive Red 2 [17804-49-8] represents a dichlorotriazinyl azo dye having the following structure:
Reactive Blue 4 [13324-20-4] represents a dichlorotriazinyl anthraquinone dye having the following structure:
Reactive Black 5 [17095-24-8] represents a two anchor vinyl sulfonyl azo dye having the following structure:
Reactive Blue 19 [2580-78-1] represents a vinyl sulfonyl anthraquinone dye having the following structure:
All dyes were found to be substantive to cotton.
Example 2: Deposition on nylon
Deposition onto nylon fabric was measured in an analogous manner to Example 1, except nylon was used a fabric.
The results are given in the table below.
Some of the hydrolysed dyes were found to be substantive to nylon.

Claims

We claim:
1. A laundry treatment composition comprising between 0.0001 to 0.1 wt % of a hydrolysed reactive dye and between 2 to 60 wt % of a surfactant.
2. A laundry treatment composition according to claim 1, wherein the hydrolysed reactive dye comprises a chromophore moiety covalently bound to an anchoring group, the anchoring group for binding to cotton, the anchoring group selected from the group consisting of: a heteroaromatic ring having at least one -OH substituent covalently bound to the heteroaromatic ring, and
SO2-C-C-OH H2 H2
A laundry formulation according to claim 2, wherein the heteroaromatic ring comprises a nitrogen heteroatom.
4. A laundry formulation according to claim 3, wherein the anchor group is of the form:
wherein: n takes a value between 1 and 3;
X is selected from the group consisting of: -Cl, -F, NHR, a quaternary ammonium group, -OR and -OH; R is selected from: an aromatic group, benzyl, a C1-C6- alkyl; and, wherein at least one X is -OH.
5. A laundry treatment composition according to claim 4, wherein R is selected from napthyl, phenyl, and -CH3.
6. A laundry treatment composition according to any one of claims 2 to 5, wherein the chromophore is selected from the group consisting of: azo, anthraquinone, phthalocyanine, formazan and triphendioaxazine..
7. A laundry treatment composition according to any one of claims 2 to 5, wherein the anchor moiety is selected from the group consisting of:
SOrC—C—OH , and H* H2 .
8. A laundry treatment composition according to any one of claims 2 to 5, wherein the chromophore is linked to the hydrolysed anchor by a bridge selected from the group consisting of: -NH-CO-, -NH-, NHCO-CH2CH2-, -NH-CO-, and -N=N-. 9. A laundry treatment composition according to claim 1, wherein the hydrolysed reactive dye is selected from the hydrolysed product of: reactive red 2, reactive blue 4, reactive black 5, and reactive blue 19.
10. A laundry treatment composition according to any preceding claim, wherein the laundry treatment composition comprises from 0.005 to 2 wt % of a fluorescer.
11. A method of treating a textile, the method comprising the steps of:
(i) treating a textile with an aqueous solution of a hydrolysed reactive dye, the aqueous solution comprising from 10 ppb to 1 ppm of the hydrolysed reactive dye and from 0.2 g/L to 3 g/L of a surfactant; and, (ii) rinsing and drying the textile.
12. A method of treating a textile according to claim 11, wherein the aqueous solution has an ionic strength from
0.001 to 0.5.
EP05771350.5A 2004-09-11 2005-08-15 Laundry treatment compositions Active EP1794274B2 (en)

Applications Claiming Priority (2)

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GBGB0420203.2A GB0420203D0 (en) 2004-09-11 2004-09-11 Laundry treatment compositions
PCT/EP2005/008861 WO2006027086A1 (en) 2004-09-11 2005-08-15 Laundry treatment compositions

Publications (3)

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EP1794274A1 true EP1794274A1 (en) 2007-06-13
EP1794274B1 EP1794274B1 (en) 2008-03-26
EP1794274B2 EP1794274B2 (en) 2019-12-18

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CN (1) CN100577787C (en)
AR (1) AR053967A1 (en)
AT (1) ATE390476T1 (en)
BR (1) BRPI0515066A (en)
DE (1) DE602005005702T2 (en)
ES (1) ES2301042T3 (en)
GB (1) GB0420203D0 (en)
WO (1) WO2006027086A1 (en)
ZA (1) ZA200701947B (en)

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WO2015112339A1 (en) 2014-01-22 2015-07-30 The Procter & Gamble Company Fabric treatment composition
WO2015112340A1 (en) 2014-01-22 2015-07-30 The Procter & Gamble Company Method of treating textile fabrics
WO2015112338A1 (en) 2014-01-22 2015-07-30 The Procter & Gamble Company Method of treating textile fabrics
WO2015112341A1 (en) 2014-01-22 2015-07-30 The Procter & Gamble Company Fabric treatment composition
WO2015126547A1 (en) 2014-02-19 2015-08-27 Milliken & Company Composition comprising benefit agent and aprotic solvent
WO2015127004A1 (en) 2014-02-19 2015-08-27 The Procter & Gamble Company Composition comprising benefit agent and aprotic solvent
WO2016081437A1 (en) 2014-11-17 2016-05-26 The Procter & Gamble Company Benefit agent delivery compositions
EP3088504A1 (en) 2015-04-29 2016-11-02 The Procter and Gamble Company Method of treating a fabric
WO2016176282A1 (en) 2015-04-29 2016-11-03 The Procter & Gamble Company Method of treating a fabric
EP3088505A1 (en) 2015-04-29 2016-11-02 The Procter and Gamble Company Method of treating a fabric
EP3088503A1 (en) 2015-04-29 2016-11-02 The Procter and Gamble Company Method of treating a fabric
EP3088502A1 (en) 2015-04-29 2016-11-02 The Procter and Gamble Company Method of treating a fabric
WO2016176240A1 (en) 2015-04-29 2016-11-03 The Procter & Gamble Company Method of treating a fabric
WO2016176241A1 (en) 2015-04-29 2016-11-03 The Procter & Gamble Company Detergent composition
EP3088506A1 (en) 2015-04-29 2016-11-02 The Procter and Gamble Company Detergent composition
WO2016176280A1 (en) 2015-04-29 2016-11-03 The Procter & Gamble Company Method of treating a fabric
WO2016176296A1 (en) 2015-04-29 2016-11-03 The Procter & Gamble Company Method of laundering a fabric
EP3674387A1 (en) 2015-04-29 2020-07-01 The Procter & Gamble Company Method of treating a fabric
WO2017091674A1 (en) 2015-11-26 2017-06-01 The Procter & Gamble Company Liquid detergent compositions comprising protease and encapsulated lipase
EP3173467A1 (en) 2015-11-26 2017-05-31 The Procter & Gamble Company Cleaning compositions comprising enzymes
EP4112707A1 (en) 2021-06-30 2023-01-04 The Procter & Gamble Company Fabric treatment
WO2023278970A1 (en) 2021-06-30 2023-01-05 The Procter & Gamble Company Fabric treatment

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DE602005005702T2 (en) 2009-04-09
ES2301042T3 (en) 2008-06-16
ATE390476T1 (en) 2008-04-15
DE602005005702D1 (en) 2008-05-08
BRPI0515066A (en) 2008-07-01
CN100577787C (en) 2010-01-06
WO2006027086A1 (en) 2006-03-16
AR053967A1 (en) 2007-05-30
ZA200701947B (en) 2008-07-30
CN101056971A (en) 2007-10-17
GB0420203D0 (en) 2004-10-13
EP1794274B1 (en) 2008-03-26
EP1794274B2 (en) 2019-12-18

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