WO2002088292A1 - Radical initiator composition - Google Patents
Radical initiator composition Download PDFInfo
- Publication number
- WO2002088292A1 WO2002088292A1 PCT/EP2002/003846 EP0203846W WO02088292A1 WO 2002088292 A1 WO2002088292 A1 WO 2002088292A1 EP 0203846 W EP0203846 W EP 0203846W WO 02088292 A1 WO02088292 A1 WO 02088292A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- radical
- initiator
- composition according
- builder
- fabric
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 102
- 239000003999 initiator Substances 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000004094 surface-active agent Substances 0.000 claims abstract description 20
- 238000010504 bond cleavage reaction Methods 0.000 claims abstract description 9
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 8
- 239000004744 fabric Substances 0.000 claims description 40
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 25
- 239000010457 zeolite Substances 0.000 claims description 22
- 229910021536 Zeolite Inorganic materials 0.000 claims description 19
- 238000005406 washing Methods 0.000 claims description 17
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 231100000489 sensitizer Toxicity 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 235000015113 tomato pastes and purées Nutrition 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
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
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
-
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
- C11D11/0088—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads the liquefied ingredients being sprayed or adsorbed onto solid particles
-
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0034—Fixed on a solid conventional detergent ingredient
-
- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2072—Aldehydes-ketones
-
- 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
-
- 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
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- 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
- C11D3/36—Organic compounds containing phosphorus
- C11D3/361—Phosphonates, phosphinates or phosphonites
Definitions
- radical initiators in some liquid compositions, incorporation in solid or semi- solid forms such as bars, powders, tablets and granules has led to practical difficulties requiring the use of special mixing methods or commercially unfavourable levels of materials. For laundry powder or tablet production these modified processes are time-consuming and add extra cost to the incorporation of the radical-initiator.
- the present invention aims to provide effective and reproducible stain treatment compositions which contain radical initiators.
- Solid washing products e.g. powders, bars, tablets
- Solid washing products give excellent bleaching effects on stains with little colour damage. This can be accomplished with low levels of initiator.
- the radical-initiator/bleach granules of the present invention are particularly advantageous in formulations that cannot contain peroxygen bleaches (as other ingredients are present which would react with the peroxygen bleach on storage) or which cannot withstand the high pH of typical peroxygen bleach formulation (e.g. certain dye transfer polymers) .
- the granules as described herein may also be used to easily deliver radical initiators to polluted water for bleaching.
- radical initiators of the present invention will act on stains without the need for agitation. This has the advantage that they can be used in simple application methods. Furthermore, mechanical damage to fabrics (such as fibrillation) can be avoided by reduction of agitation.
- the preferred radical photo- initiators of the present invention have the advantage that they are stable in solution if kept in the substantial absence of light. It is found that they do not degrade spontaneously on storage .
- radical initiators are selected from hydrogen abstraction radical photoinitiators, bond-cleavage radical photoinitiators and mixtures thereof.
- Suitable examples of hydrogen abstraction radical photoinitiators X include benzophenones, acetophenones, pyrazines, quinones and benzils.
- alpha amino ketones particularly those containing a benzoyl moiety, otherwise called alpha-amino acetophenones, for example 2-methyl 1- [4 -phenyl] -2- morpholinopropan-1-one (Irgacure 907, trade mark), (2- benzyl-2 -dimethyl ' amino- 1- (4-morpholinophenyl) -butan-1- one (Irgacure 369, trade mark);
- alphahydroxy ketones particularly alpha-hydroxy acetophenones, eg (1- [4- (2-hydroxyethoxy) -phenyl] -2- hydroxy-2 -methyl-1-propan-l-one) (Irgacure 2959, trade mark), 1 -hydroxy-cyclohexyl-phenyl-ketone (Irgacure 184, trade mark), oligo [2 -hydroxy 2-methyl-l- [4 (1- methyl) phenyl] propanone (Esacure KIP 150, trade mark);
- Suitable radical photoinitiators are disclosed in WO 9607662 (trisacyl phosphine oxides) , US 5399782 (phosphine sulphides), US 5410060, EP-A-57474, EP-A-73413 (phosphine oxides), EP-A-088050, EP-A-0117233 , EP-A-0138754 , EP-A-0446175 and US 4559371.
- Suitable photoinitiators are disclosed for example in EP-A-0003002 in the name of Ciba Geigy, EP-A-0446175 in the name of Ciba Geigy, GB 2259704 in the name of Ciba Geigy (alkyl bisacyl phosphine oxides) , US 4792632 (bisacyl phosphine oxides) , US 5554663 in the name of Ciba Geigy (alpha amino acetophenones) , US 5767169 (alkoxy phenyl substituted bisacyl phosphine oxides) and US 4719297 (acylphosphine compounds) .
- Radical photoinitiators are discussed in general in A.F. Cunningham, V. Desorby, K. Dietliker, R. Husler and D.G. Leppard, Chemia 48 (1994) 423-426. They are discussed in H. F. Gruber Prog. Polym. Sci. 17(1992) 953-1044.
- radical photoinitiators all react through their excited triplet state, to reduce the influence of the cage effect.
- the radical photoinitiator suitably undergoes one of the reactions set out above when excited by radiation falling generally in the range 290-800 nm.
- natural sunlight which comprises light in this region, will be suitable for causing the radical photoinitiator to undergo one of the reactions described above.
- the radical photo initiator has a maximum extinction coefficient in the ultraviolet range (290-400 nm) which is greater than
- the granule to the powder/tablet/bar should occur in the absence of significant levels of UV light to prevent photo-degradation of the product. Additionally the product container should not allow light below 440 nm to penetrate. This may be achieved by use of suitable optical barriers including plastics, sunscreens or dyes
- zeolite MAP having a silicon to aluminium ratio not exceeding 1.07, more preferably about 1.00.
- the calcium binding capacity of zeolite MAP is generally at least 150 mg CaO per g of anhydrous material.
- Organic builders that may also be present include: polycarboxylate polymers such as: polyacrylates, acrylic/maleic copolymers, and acrylic phosphinates; monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di- and tri-succinates, carboyxmethyloxysuccinates, carboxy ethyloxymalonates , dipicolinates , hydroyxethyliminodiacetates , alkyl- and alkenyl-malonates and succinates, and, sulphonated fatty acid salts. This list is not intended to be exhaustive.
- polycarboxylate polymers such as: polyacrylates, acrylic/maleic copolymers, and acrylic phosphinates
- monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di- and tri-succinates, carboyxmethyloxysucc
- Radical terminators may optionally be present in the compositions of the present invention.
- the non-reactive products can, for example, be relatively stable (and relatively unreactive) radicals or non-radical molecules or ions .
- Mixtures of nonionic surfactant may be used.
- Such variant methods include extended exposure to light prior to a final rinsing step, or a pre- treatment of stains with a composition according to the invention. Where a composition of the present invention is intended for use in one of these variant methods, it will typically be packaged together with instructions relating to that method.
- a granule was created by slowly adding 10% weight of Lucirin TPO-L to the zeolite DoucilTM A24 with vigorous mixing.
- the organic builder Sokalam CP5 (ex BASF) , a maleic Anhydride and acrylic acid copolymer, was then added till a good granule was created.
- the resulting granule had the following weight composition:
- Esacure KIP150 was cooled to 0 C and then pulverised by hammer. The resulting powder was mixed with dry ice to obtain a cold mixture. This mixture was mixed with powdered sodium sulphate and then granulated with Sokalam CP5 and warmed to room temperature. The granules were then dried at
- the granule composition was:
- examples 1,2 & 4-6 were added to Persil Colour Care Powder to give 0.1% weight initiator in the powder.
- the powders were used to wash the tomato stains of example 1, (30 mins, 40 C wash, 5g/l powder, 2 rinses, a liquor to cloth ratio of 10:1 and wash only contained stained cloth) and then irradiated in a WeatherometerTM ('WOM') for 12 minutes. The results are given in table 2.
- the nonionic surfactant Synperionic A20 is a waxy solid at room temperature. It was melted by heating and the semi- solid photo-initiator Esacure KIP 150 was added to give a 50:50 (weight) mixture. This was allowed to cool, and when the mixture became viscous, the zeolite Doucil A24 was added and the mixture mixed with a pestle and mortar. This produced granules which contained 12.5% weight photoinitiator. The granules were added to Persil Colour Care washing powder so that the powder contained 0.2% Esacure KIP 150.
- Lucirin TPO-L granules were made according to example 1. Following their creation the granules were separated into different sizes by sieving. To see the effect of granule size in performance the granules added to Persil Powder and used to wash cotton stained with Palm oil in a manner analogous to example 8. A wash was also conducted without initiator added and with initiator added directly to the wash liquor. The results are given in table 3 below:
- Granules were made according to examples 2, 5 and 7 and added to Persil Colour Care washing powder to give 0.2% of radical photoinitiator on weight of formulation.
- the powders were stored in an open container at 28 C and 70% relative humidity for 20 weeks. The performance of the powders was then tested by washing then irradiating oily tomato stains and comparing to a control that had also been stored but without photoinitiator present.
- the 3 powders which contained initiator gave excellent bleaching of the stain, compared to the control, showing that the granules store well .
- Granules were made according to example 2 and stored in 2 washing powders which had zeolite and phosphate as the predominate builders respectively and percarbonate and perborate as a hydrogen peroxide source respectively. Bleach wash tests on tomato stains after 1 weeks storage at 37 C and 70% humidity in closed cardboard boxes showed that photo-bleaching due to the presence of Esacure KIP still occurred.
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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)
- Detergent Compositions (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0110414A GB0110414D0 (en) | 2001-04-27 | 2001-04-27 | Radical initiator composition |
GB0110414.0 | 2001-04-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002088292A1 true WO2002088292A1 (en) | 2002-11-07 |
WO2002088292A8 WO2002088292A8 (en) | 2003-02-27 |
Family
ID=9913629
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/003846 WO2002088292A1 (en) | 2001-04-27 | 2002-04-08 | Radical initiator composition |
Country Status (3)
Country | Link |
---|---|
AR (1) | AR033477A1 (en) |
GB (1) | GB0110414D0 (en) |
WO (1) | WO2002088292A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010099997A1 (en) * | 2009-03-05 | 2010-09-10 | Unilever Plc | Dye radical initiators |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0437988A2 (en) * | 1989-12-08 | 1991-07-24 | Rhone-Poulenc Chimie | Detergent additive based on polyphosphate and an active optical agent, method of its production and its use in detergent composition |
WO1999051714A2 (en) * | 1998-04-07 | 1999-10-14 | Unilever Plc | Coloured granular composition for use in particulate detergent compositions |
WO2001007549A1 (en) * | 1999-07-23 | 2001-02-01 | Unilever Plc | Fabric care treatment composition and a method of treating fabric |
-
2001
- 2001-04-27 GB GB0110414A patent/GB0110414D0/en not_active Ceased
-
2002
- 2002-04-08 WO PCT/EP2002/003846 patent/WO2002088292A1/en not_active Application Discontinuation
- 2002-04-26 AR ARP020101523A patent/AR033477A1/en not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0437988A2 (en) * | 1989-12-08 | 1991-07-24 | Rhone-Poulenc Chimie | Detergent additive based on polyphosphate and an active optical agent, method of its production and its use in detergent composition |
WO1999051714A2 (en) * | 1998-04-07 | 1999-10-14 | Unilever Plc | Coloured granular composition for use in particulate detergent compositions |
WO2001007549A1 (en) * | 1999-07-23 | 2001-02-01 | Unilever Plc | Fabric care treatment composition and a method of treating fabric |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010099997A1 (en) * | 2009-03-05 | 2010-09-10 | Unilever Plc | Dye radical initiators |
Also Published As
Publication number | Publication date |
---|---|
WO2002088292A8 (en) | 2003-02-27 |
GB0110414D0 (en) | 2001-06-20 |
AR033477A1 (en) | 2003-12-17 |
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