EP0379312A1 - Photobleiche-Zusammensetzungen und Verfahren zu ihrer Herstellung - Google Patents
Photobleiche-Zusammensetzungen und Verfahren zu ihrer Herstellung Download PDFInfo
- Publication number
- EP0379312A1 EP0379312A1 EP90300349A EP90300349A EP0379312A1 EP 0379312 A1 EP0379312 A1 EP 0379312A1 EP 90300349 A EP90300349 A EP 90300349A EP 90300349 A EP90300349 A EP 90300349A EP 0379312 A1 EP0379312 A1 EP 0379312A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- photobleach
- water
- soluble
- insoluble
- quaternary nitrogen
- 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.)
- Withdrawn
Links
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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0063—Photo- activating compounds
-
- 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/28—Heterocyclic compounds containing nitrogen in the ring
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/50—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs by irradiation or ozonisation
Definitions
- the present invention relates to photobleach compositions.
- Photobleaches are materials included in detergent laundry compositions intended for use in parts of the world with high incident sunlight. They produce a bleaching effect on laundry on being exposed to sunlight when the laundry is dried in the open air.
- GB1 372 035 discloses a bleaching process in which textiles are treated with a detergent composition containing photoactivators and exposed to light.
- photactivators are porphyrins and phthalocyanines with anionic substituents, which may be zinc phthalocyanines.
- GB 1 408 144 discloses a similar process in which a peroxy compound is used to provide a source of oxygen additional to that provided by oxygen from the atmosphere.
- US 4 033 718 discloses a textile bleaching process which is similar to those described above, but which uses a specific mixture of sulphonated zinc phthalocyanines.
- US 4 166 718 discloses a process for bleaching textiles by oxygen in the presence of light using a photactivator which is a water-soluble aluminium phthalocyanine.
- a photactivator which is a water-soluble aluminium phthalocyanine.
- the specification indicates that water-solubility is necessary for a photoactivator.
- US 4 648 992 discloses novel water-soluble phthalocyanine compounds which may be used as photobleaching agents. Various elements are listed among the central atoms which may be present.
- Conventional photobleaching compositions contain compounds which are closely related to substances which are used as fabric dyes. This does not cause problems when the compositions are used in normal wash liquids (i.e. the dilute aqueous medium in which clothes are washed).
- normal wash liquids i.e. the dilute aqueous medium in which clothes are washed.
- persons washing laundry with localised stains or dirt (spots) are often in the habit of applying a concentrated solution of detergent to the spots before the main wash. This application of a concentrated solution to a spot is particularly likely to occur if the detergent composition is supplied to the user as a liquid detergent concentrate rather than a powder. If concentrated solutions of conventional photobleaches are applied to textiles then staining of the textiles is likely to result. This staining is not removed by the subsequent washing step in the dilute wash liquid.
- a photobleach which is a substantially water-insoluble photobleach substantially free of water-soluble photobleach.
- a laundry detergent composition comprises a photobleach consisting of a substantially water-insoluble photobleach substantially free of water-soluble photobleach.
- novel photobleach material of the present invention is water-insoluble in the sense that it is substantially free of constituents which are soluble in pure water and which can thus produce undesirable staining. Nevertheless the material is dispersible in the dilute wash liquid in which the main washing action takes place.
- the substantially water-insoluble photobleach is preferably an insoluble quaternary nitrogen salt of a water-soluble photobleach.
- the insoluble quaternary nitrogen salt is formed from a relatively high molecular weight quaternary nitrogen compound which is sufficiently soluble in water to allow it to be dissolved to give an aqueous reactant solution but which reacts with the other component to give an insoluble precipitate.
- the solubility of the water-soluble quaternary salt will be affected by the counter anion and a preferred counter anion is the chloride ion. Among other counterions which can be used are the methylsulphate ion.
- the quaternary nitrogen compound may be a quaternary ammonium compound or may be a quaternary imidazolidinium compound. Examples of suitable quaternary nitrogen compounds are the quaternary nitrogen compounds containing one or two long chain alkyl groups (e.g. from C10 to C22). A specific compound which can be used is di(hydrogenated tallow) dimethylammonium chloride.
- the other component which forms the water-insoluble ammonium salt is a water-soluble photobleach.
- photobleaches are well-known. Photobleaches are selected so as not to have a high affinity ("substantivity") for textile fibres which can cause colouration when photobleach is used at low dilutions.
- a preferred class of water-soluble photobleaches is constituted by the anionically-substituted porphines.
- the porphine may be metallated for example with Zn(II), Al(III), Ca(II), Cd(II), Mg(II), Sc(III), Sn(IV), or Fe(II).
- the porphines may be defined by the formula: in which
- the preferred porphine compounds are the tetraaza tetrabenzo derivatives, namely the phthalocyanines i.e. those compounds in which X is N in formula (I) above and adjacent pairs of R are joined together to form benzene rings.
- the substantially water-insoluble salt may be formed by the reaction of aqueous solutions of the starting materials.
- the precipitated product may be sufficiently free of water-soluble fabric substantive materials capable of causing staining to be used in detergent compositions without further treatment. However, it may be free of soluble coloured components. It may be desirable to subject the precipitate to a solvent extraction step with a hydrophobic solvent (e.g. carbon tetrachloride) to recover a solution of the desired material before removing the solvent and carrying out a water washing step.
- a hydrophobic solvent e.g. carbon tetrachloride
- the photobleach material of the present invention may be incorporated into laundry detergents, but is particularly suitable for incorporation into liquid laundry detergents.
- photobleach material to a liquid laundry detergent in the form of a pre-dispersion in a non-ionic surfactant, for example a C12-C15 alkyl ethoxylate.
- a non-ionic surfactant for example a C12-C15 alkyl ethoxylate.
- the quantities of photobleach which may be incorporated into detergent compositions may for example be in the range 0.01 to 0.5% wt based on the weight of the powder or liquid sold to the consumer.
- Tinolux BBS Tinolux BBS
- Tinolux BBS a tetrabenzotetraaza porphine believed to be an A1 salt of a water-soluble phthalocyanine made in accordance with US 4 166 718.
- a water insoluble quaternary ammonium salt of the phthalocyanine was extracted into carbon tetrachloride.
- the carbon tetrachloride solution was washed with water, dried, and the carbon tetrachloride was removed by evaporation.
- the solid product recovered from the carbon tetrachloride was added to water (1 l) and stirred vigorously with a high speed mixer for several minutes. This removed any residual water soluble material which might have been carried over from the starting material. The solid product was recovered by filtration and the washing step was continued until the filtrate was colourless.
- a pre-dispersion of the water-insoluble photobleach was made up by dispersing the required amount of photobleach in a micellar solution of an alkyl ethoxylate of HLB in the range 11-14.
- a liquid laundry detergent containing the photobleach material prepared above was prepared by agitating sufficient of the pre-dispersion with a conventional heavy duty laundry liquid composition containing anionic and non-ionic surfactants to give a concentration of 0.05 %wt.
- a liquid laundry detergent was prepared having the same composition as that prepared in Example 1 except that it did not contain the novel photobleach but contained 0.05% wt of the water-soluble phthalocyanine photobleach ("Tinolux BBS”) used as starting material in Example 1.
- Tinolux BBS water-soluble phthalocyanine photobleach
- a liquid laundry detergent was prepared having the same composition as that prepared in Example 1 except that it did not contain any photobleach.
- Example 1 1 ml of the liquid detergent prepared as in Example 1 was applied to a piece of white cotton cloth. Sufficient time was allowed for the liquid detergent to soak into the cloth. The detergent was rinsed off under a stream of cold water, and the cloth was then dried. No blue stain attributable to the photobleach could be seen on the cloth.
- Example 1 2.5g of the liquid detergent composition of Example 1 was added to 500ml of water at 60°C.
- Two standard cotton cloth swatches stained with red wine (each 100mm X 100mm)(EMPA) were added to the liquid. After 15 minutes the swatches were removed and rinsed with cold water.
- One of the swatches was dried while illuminated with a 50 W quartz-halogen lamp mounted at 150mm from the cloth swatch (to simulate the effect of sunlight). The cloth was rewetted from time to time with distilled water. The other cloth was allowed to dry in normal ambient laboratory lighting.
- the amount of stain removl was estimated by measuring the reflectance of the fabric before and after washing. Drying conditions % stain removal ambient lighting 21 quartz-halogen 41
- Example 1 A comparison of the result for Example 1 and comparative Test A clearly shows the improved spotting performance of the photobleach of the invention.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898900807A GB8900807D0 (en) | 1989-01-14 | 1989-01-14 | Bleach compositions |
GB8900807 | 1989-01-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0379312A1 true EP0379312A1 (de) | 1990-07-25 |
Family
ID=10650032
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90300349A Withdrawn EP0379312A1 (de) | 1989-01-14 | 1990-01-11 | Photobleiche-Zusammensetzungen und Verfahren zu ihrer Herstellung |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0379312A1 (de) |
GB (1) | GB8900807D0 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997043394A2 (en) * | 1996-05-17 | 1997-11-20 | The Procter & Gamble Company | Detergent composition |
WO1997043393A2 (en) * | 1996-05-17 | 1997-11-20 | The Procter & Gamble Company | Detergent composition |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2150741A (en) * | 1935-06-04 | 1939-03-14 | Ici Ltd | Manufacture of phthalocyanine coloring matters soluble in organic media |
US4166718A (en) * | 1977-03-25 | 1979-09-04 | Ciba-Geigy Corporation | Process for bleaching textiles |
EP0035470A1 (de) * | 1980-02-29 | 1981-09-09 | Ciba-Geigy Ag | Textilbehandlungsmittel |
EP0054992A1 (de) * | 1980-12-22 | 1982-06-30 | Unilever N.V. | Einen Photoaktivator enthaltende Zusammensetzung mit verbesserter Bleichwirkung |
EP0087833A1 (de) * | 1982-02-19 | 1983-09-07 | Unilever N.V. | Photobleichmittelsystem, Zusammensetzung und Verfahren |
DE3410611A1 (de) * | 1983-03-25 | 1984-10-04 | Ciba-Geigy Ag, Basel | Verfahren zur herstellung von festen photoaktivatorpraeparaten |
-
1989
- 1989-01-14 GB GB898900807A patent/GB8900807D0/en active Pending
-
1990
- 1990-01-11 EP EP90300349A patent/EP0379312A1/de not_active Withdrawn
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2150741A (en) * | 1935-06-04 | 1939-03-14 | Ici Ltd | Manufacture of phthalocyanine coloring matters soluble in organic media |
US4166718A (en) * | 1977-03-25 | 1979-09-04 | Ciba-Geigy Corporation | Process for bleaching textiles |
EP0035470A1 (de) * | 1980-02-29 | 1981-09-09 | Ciba-Geigy Ag | Textilbehandlungsmittel |
EP0054992A1 (de) * | 1980-12-22 | 1982-06-30 | Unilever N.V. | Einen Photoaktivator enthaltende Zusammensetzung mit verbesserter Bleichwirkung |
EP0087833A1 (de) * | 1982-02-19 | 1983-09-07 | Unilever N.V. | Photobleichmittelsystem, Zusammensetzung und Verfahren |
DE3410611A1 (de) * | 1983-03-25 | 1984-10-04 | Ciba-Geigy Ag, Basel | Verfahren zur herstellung von festen photoaktivatorpraeparaten |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997043394A2 (en) * | 1996-05-17 | 1997-11-20 | The Procter & Gamble Company | Detergent composition |
WO1997043393A2 (en) * | 1996-05-17 | 1997-11-20 | The Procter & Gamble Company | Detergent composition |
WO1997043394A3 (en) * | 1996-05-17 | 1997-12-24 | Procter & Gamble | Detergent composition |
WO1997043393A3 (en) * | 1996-05-17 | 1997-12-31 | Procter & Gamble | Detergent composition |
US6136769A (en) * | 1996-05-17 | 2000-10-24 | The Procter & Gamble Company | Alkoxylated cationic detergency ingredients |
Also Published As
Publication number | Publication date |
---|---|
GB8900807D0 (en) | 1989-03-08 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): ES GB GR IT |
|
17P | Request for examination filed |
Effective date: 19910103 |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: THE BRITISH PETROLEUM COMPANY P.L.C. |
|
17Q | First examination report despatched |
Effective date: 19930820 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 19940301 |