EP1478724A1 - Prozess zum behandeln von textilen fasermaterialien - Google Patents

Prozess zum behandeln von textilen fasermaterialien

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Publication number
EP1478724A1
EP1478724A1 EP03706527A EP03706527A EP1478724A1 EP 1478724 A1 EP1478724 A1 EP 1478724A1 EP 03706527 A EP03706527 A EP 03706527A EP 03706527 A EP03706527 A EP 03706527A EP 1478724 A1 EP1478724 A1 EP 1478724A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
substituted
unsubstituted
peroxide
formula
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
EP03706527A
Other languages
English (en)
French (fr)
Other versions
EP1478724B1 (de
Inventor
Jürgen Kaschig
Robert Hochberg
Oliver Becherer
Georges Metzger
Claude Eckhardt
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to EP06118810A priority Critical patent/EP1724333A1/de
Priority to EP03706527A priority patent/EP1478724B1/de
Publication of EP1478724A1 publication Critical patent/EP1478724A1/de
Application granted granted Critical
Publication of EP1478724B1 publication Critical patent/EP1478724B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D3/42—Brightening agents ; Blueing agents
    • 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3932—Inorganic compounds or complexes

Definitions

  • the present invention is directed to detergent formulations containing certain fluorescent whitening agents and a peroxide, a peroxide activator and/or a bleaching catalyst.
  • the present invention provides, as a first aspect, a detergent composition comprising at least one compound of formula wherein
  • R, and R are, independently of each other, hydrogen or unsubstituted or substituted d-C ⁇ alkyl
  • X X 2 , X3 and X are, independently of each other, -N(R 3 )R 4 or -OR 5 , wherein R 3 and R 4 are hydrogen; cyano; d-C 8 alkyl which is unsubstituted or substituted by hydroxy, carboxy, cyano, -CONH 2 or phenyl and wherein the d-C 8 alkyl group is uninterrupted or interrupted by
  • R 5 is d-C 6 alkyl which is unsubstituted or substituted by hydroxy
  • M is hydrogen or a cation, and wherein the detergent contains a peroxide, a peroxide activator and/or a bleaching catalyst.
  • CrC 8 alkyl may be methyl, ethyl, n- or isopropyl, n-, sec- or t-butyl, or linear or branched pentyl, hexyl, heptyl or octyl.
  • Preferred are d-C 4 alkyl groups.
  • the alkyl groups given for R ⁇ and R 2 are substituted examples of possible substituents are hydroxyl, halogen, like fluorine, chlorine or bromine, sulfo, sulfato, carboxy and d-C 4 alkoxy, like methoxy and ethoxy.
  • substituents of such alkyl groups are, for example, cyano, -CONH 2 and phenyl.
  • Preferred substituents are hydroxy, carboxy, cyano, - CONH 2 and phenyl, especially hydroxy and carboxy.
  • highly preferred substituents are hydroxy and d-C 4 alkoxy, especially hydroxy.
  • the alkyl groups can also be uninterrupted or interrupted by -O- (in case of alkyl groups containing two or more carbon atoms).
  • C 5 -C 7 cycloalkyl groups are cyclopentyl and especially cyclohexyl. These groups can be substituted by d-C 4 -alkyl, like methyl. Preferred are the corresponding unsubstituted cycloalkyl groups.
  • d-C 4 alkyl may be methyl, ethyl, n- or isopropyl, n-, sec- or t-butyl, especially methyl.
  • piperidine or pyrrolidine ring such a ring system can be unsubstituted or substituted by d-C 4 alkyl, especially methyl. Preferred are the unsubstituted ring systems.
  • the cation M is preferably an alkali metal atom, an alkaline earth metal atom, ammonium or a cation formed from an amine.
  • Preferred are Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-d-Ctalkylammonium, mono-, di- or tri-C 2 -C 4 -hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C r C -alkyl and C 2 -C 4 -hydroxyalkyl groups.
  • Highly preferred is sodium.
  • Ri and R 2 are preferably hydrogen or d-C alkyl, especially hydrogen.
  • R 3 and R 4 are preferably hydrogen; cyano; d-C 8 alkyl which is unsubstituted or substituted by hydroxy, carboxy, cyano, -CONH 2 or phenyl, especially by hydroxy or carboxy, and wherein the d-C 8 alkyl group is uninterrupted or interrupted by -O-; unsubstituted or d-dalkyl- substituted C 5 -C 7 cycloalkyl, especially cyclohexyl; or R 3 and R 4 , together with the nitrogen atom linking them, form an unsubstituted or d-C 4 alkyl-substituted morpholino, piperidine or pyrrolidine ring.
  • R 3 and R are hydrogen, unsubstituted or hydroxy-substituted C C 8 alkyl, unsubstituted or C ⁇ -C 4 alkyl-substituted C 5 -C 7 cycloalkyl, or R 3 and R , together with the nitrogen atom linking them, form an unsubstituted or d-C 4 alkyl-substituted morpholino, piperidine or pyrrolidine ring.
  • R 3 and R 4 are hydrogen, unsubstituted or hydroxy-substituted d-C 8 alkyl, or R 3 and R 4 , together with the nitrogen atom linking them, form an unsubstituted or d-dalkyl-substituted morpholino, piperidine or pyrrolidine ring.
  • R 3 and R 4 are hydrogen, unsubstituted or hydroxy-substituted d-C 8 alkyl, or R 3 and R 4 , together with the nitrogen atom linking them, form an unsubstituted or d-dalkyl-substituted morpholino, piperidine or pyrrolidine ring.
  • Most preferred are unsubstituted or d-C 4 alkyl-substituted morpholino, piperidine or pyrrolidine rings, especially morpholino, formed by R 3 and R 4 together with the nitrogen atom linking them.
  • Examples of -N(R 3 )R 4 groups are -NH 2> -NHCH 3 , -NHC 2 H 5 , -NH(n-C 3 H 7 ), -NH(i-C 3 H 7 ), -NH(i-C 4 H 9 ), -N(CH 3 ) 2 , -N(C 2 H 5 ) 2 , -N(i-C 3 H 7 ) 2 , -NH(CH 2 CH 2 OH), -N(CH 2 CH 2 OH) 2 , -N(CH 2 CH(OH)CH 3 ) 2 , -N(CH 3 )(CH 2 CH 2 OH), -N(C 2 H 5 )(CH 2 CH 2 OH), -N(i-C3H 7 )(CH 2 CH 2 CH 2 OH), -NH(CH 2 CH(OH)CH3), -N(C 2 H 5 )(CH 2 CH(OH)CH 3 ), -NH(CH 2 CH 2 OCH 3
  • R 5 is preferably d-C ⁇ alkyl, especially d-dalkyl, which is unsubstituted or substituted by hydroxy. Highly preferred for R 5 is methyl or ethyl, especially methyl.
  • X L X 2 , X 3 and X 4 are preferably a radical of formula -N(R 3 )R 4 .
  • X T and X 3 have preferably the same meanings.
  • X 2 and X 4 have preferably the same meanings.
  • the four radicals X ⁇ X 2 , X 3 and X 4 do not have identical meanings.
  • Ri and R 2 are hydrogen or d-dalkyl
  • R 3 and R 4 are hydrogen; cyano; d-C 8 alkyl which is unsubstituted or substituted by hydroxy, carboxy, cyano, -CONH 2 or phenyl and wherein the d-C 8 alkyl group is uninterrupted or interrupted by -O-; unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 7 cycloalkyl; or R 3 and R 4) together with the nitrogen atom linking them, form an unsubstituted or d-C 4 alkyl-substituted morpholino, piperidine or pyrrolidine ring; and
  • R 5 is d-C 8 alkyl which is unsubstituted or substituted by hydroxy.
  • Xi and X 3 are amino, and
  • X 2 and X 4 are a radical of formula -N(R 3 )R 4 , wherein R 3 and R 4 are hydrogen; cyano; d-
  • C 8 alkyl group is uninterrupted or interrupted by -O-; unsubstituted or d-C 4 alkyl-substituted cyclohexyl; or R 3 and R 4 , together with the nitrogen atom linking them, form an unsubstituted or d-C 4 alkyl-substituted morpholino, piperidine or pyrrolidine ring.
  • R 3 and R 4 the above preferences apply.
  • Xi and X 3 are amino
  • X 2 and X 4 are a radical of formula -N(R 3 )R 4
  • R 3 and R are hydrogen, unsubstituted or hydroxy-substituted d-C 8 alkyl, unsubstituted or d-C 4 alkyl-substituted cyclopentyl or cyclohexyl, or R 3 and R 4 , together with the nitrogen atom linking them, form an unsubstituted or d-C 4 alkyl-substituted morpholino, piperidine or pyrrolidine ring.
  • the compounds of formula (1) are known or can be prepared in analogy to known processes.
  • Compounds of formula (1) may be produced by reacting, under known reaction conditions, cyanuric chloride, successively, in any desired sequence, with each of 4,4'-diaminostilbene-2,2'- disulfonic acid, and amino compounds capable of introducing the groups Xi, X 2 , X 3 and X 4 .
  • cyanuric chloride a compound capable of introducing the groups Xi, X 2 , X 3 and X 4 .
  • 2 moles of cyanuric chloride are initially reacted with 1 mole of 4,4'-diaminostilbene-2,2'- disulfonic acid and then reacting the intermediate obtained in any order with amino compounds capable of introducing the groups Xi, X 2 , X 3 and X 4 .
  • Compounds of formula (1 ) containing a radical of formula -OR 5 can for example be prepared by first reacting cyanuric chloride with the correponding alcohol HOR 5 , reacting the product obtained with 4,4'-diaminostilbene-2,2'- disulfonic acid and then reacting the intermediate with further compounds capable of introducing the remaining groups of X , X 2 , X 3 and X 4 . The last reaction is preferably carried out with the corresponding amines.
  • the detergent compositions used preferably comprise i) 1-70% of an anionic surfactant and/or a nonionic surfactant; ii) 0-75% of a builder; iii) 0.5-30% of a peroxide; iv) 0.5-10% of a peroxide activator and/or 0.1-2% of a bleaching catalyst ; v) 0.001-5% of a compound of formula (1); and vi) 0-5% of at least one enzyme selected from the group consisting of cellulase, protease, amylase and lipase.
  • the detergent compositions used comprise i) 5-70% of an anionic surfactant and/or a nonionic surfactant; ii) 5-70% of a builder; iii) 0.5-30% of a peroxide; iv) 0.5-10% of a peroxide activator and/or 0.1-2% of a bleaching catalyst; v) 0.01-5% of a compound of formula (1); and vi) 0.05-5% of at least one enzyme selected from the group consisting of cellulase, protease, amylase and lipase.
  • an amount of compounds of formula (1) of 0.001-5%, especially an amount of 0.01-5% is used. Highly preferred is an amount of 0.05-5%, especially 0.05 to 2%.
  • amounts given in percent are to be understood as being percent by weight, based on the total weight, unless otherwise stated.
  • the detergent may be formulated as a solid, as an aqueous liquid comprising, e.g., 5-50, preferably 10-35% water or as a non-aqueous liquid detergent, containing not more than 5, preferably 0-1 wt.% of water, and based on a suspension of a builder in a non-ionic surfactant, as described, e.g., in GB-A-2158454.
  • the anionic surfactant component may be, e.g., an alkylbenzenesulfonate, an alkylsulfate, an alkylethersulfate, an olefinsulfonate, an alkanesulfonate, a fatty acid salt, an alkyl or alkenyl ether carboxylate or an ⁇ -sulfofatty acid salt or an ester thereof.
  • alkylbenzenesulfonates having 10 to 20 carbon atoms in the alkyl group
  • alkylsulfates having 8 to 18 carbon atoms
  • alkylethersulfates having 8 to 18 carbon atoms
  • fatty acid salts being derived from palm oil or tallow and having 8 to 18 carbon atoms.
  • the average molar number of ethylene oxide added in the alkylethersulfate is preferably 1 to 20, preferably 1 to 10.
  • the salts are preferably derived from an alkaline metal like sodium and potassium, especially sodium.
  • alkali metal sarcosinates of formula R-CO(R 1 )CH 2 COOM 1 in which R is alkyl or alkenyl having 9-17 carbon atoms in the alkyl or alkenyl radical, R 1 is d-C 4 alkyl and M 1 is alkali metal, especially sodium.
  • the nonionic surfactant component may be, e.g., primary and secondary alcohol ethoxylates, especially the C 8 -C 20 aliphatic alcohols ethoxylated with an average of from 1 to 20 moles of ethylene oxide per mole of alcohol, and more especially the C 10 -C 15 primary and secondary aliphatic alcohols ethoxylated with an average of from 1 to 10 moles of ethylene oxide per mole of alcohol.
  • Non-ethoxylated nonionic surfactants include alkylpolyglycosides, glycerol monoethers, and polyhydroxyamides (glucamide).
  • the total amount of anionic surfactant and nonionic surfactant is preferably 5-50% by weight, preferably 5-40% by weight and more preferably 5-30% by weight. As to these surfactants it is preferred that the lower limit is 10% by weight.
  • the builder component may be an alkali metal phosphate, especially a tripolyphosphate; a carbonate or bicarbonate, especially the sodium salts thereof; a silicate or disilicate; an aluminosilicate; a polycarboxylate; a polycarboxylic acid; an organic phosphonate; or an aminoalkylene poly (alkylene phosphonate); or a mixture of these.
  • Preferred silicates are crystalline layered sodium silicates of the formula NaHSi m O 2m+ ⁇ -pH 2 O or Na 2 Si m O 2m+1 .pH 2 O in which m is a number from 1.9 to 4 and p is 0 to 20.
  • Preferred aluminosilicates are the commercially-available synthetic materials designated as
  • Zeolites A, B, X, and HS or mixtures of these. Zeolite A is preferred.
  • Preferred polycarboxylates include hydroxypolycarboxylates, in particular citrates, polyacrylates and their copolymers with maleic anhydride.
  • Preferred polycarboxylic acids include nitrilotriacetic acid and ethylene diamine tetra-acetic acid.
  • Preferred organic phosphonates or aminoalkylene poly (alkylene phosphonates) are alkali metal ethane 1 -hydroxy diphosphonates, nitrilo trimethylene phosphonates, ethylene diamine tetra methylene phosphonates and diethylene triamine penta methylene phosphonates.
  • the amount of builders is preferably 5-70% by weight, preferably 5-60% by weight and more preferably 10-60% by weight. As to the builders it is preferred that the lower limit is 15% by weight, especially 20% by weight.
  • Suitable peroxide components include, for example, the organic and inorganic peroxides (like sodium peroxides) known in the literature and available commercially that bleach textile materials at conventional washing temperatures, for example at from 5 to 95°C.
  • the organic peroxides are, for example, monoperoxides or polyperoxides having alkyl chains of at least 3, preferably 6 to 20, carbon atoms; in particular diperoxydicarboxylates having 6 to 12 C atoms, such as diperoxyperazelates, diperoxypersebacates, diperoxyphthalates and/or diperoxydodecanedioates, especially their corresponding free acids, are of interest.
  • very active inorganic peroxides such as persulphate, perborate and/or percarbonate. It is, of course, also possible to employ mixtures of organic and/or inorganic peroxides.
  • the amount of peroxide is preferably 0.5-30% by weight, preferably 1 -20% by weight and more preferably 1-15% by weight.
  • the lower limit is preferably 2% by weight, especially 5% by weight.
  • the peroxides are preferably activated by the inclusion of a bleach activator.
  • a bleach activator Preferred are such compounds that, under perhydrolysis conditions, yield unsubstituted or substituted perbenzo- and/or peroxo-carboxylic acids having from 1 to 10 carbon atoms, especially from 2 to 4 carbon atoms.
  • Suitable compounds include those that carry O- and/or N-acyl groups having the said number of carbon atoms and/or unsubstituted or substituted benzoyl groups.
  • polyacylated alkylenediamines especially tetraacetylethylenediamine (TAED), acylated glycolurils, especially tetraacetylglycoluril (TAGU), N,N-diacetyl-N,N-dimethyl-urea (DDU), acylated triazine derivatives, especially 1 ,5-diacetyl-2,4-dioxohexahydro-1 ,3,5-triazine (DADHT), compounds of formula wherein R is a sulfonate group, a carboxylic acid group or a carboxylate group, and wherein R' is linear or branched (C 7 -C 15 )alkyl; also activators that are known under the names SNOBS, SLOBS, NOBS and DOBA, acylated polyhydric alcohols, especially triacetin, ethylene glycol diacetate and 2,5-diacetoxy-2,5-di
  • the amount of bleach activator is preferably 0-10% by weight, preferably 0-8% by weight.
  • the lower limit is preferably 0.5% by weight, especially 1% by weight.
  • Bleaching catalysts which may be added, include, e.g., enzymatic peroxide precursors and/or metal complexes.
  • Preferred metal complexes are manganese, cobalt or iron complexes such as manganese or iron phthalocyanines or the complexes described in EP-A- 0509787.
  • the amount is preferably 0.005 to 2% by weight, more preferably 0.01 to 2% by weight, especially 0.05 to 2% by weight. Highly preferred is an amount of 0.1-2% by weight.
  • bleaching catalysts As examples for bleaching catalysts the following are mentioned:
  • the detergent can optionally contain enzymes. Enzymes can be added to detergents for stain removal.
  • the enzymes usually improve the performance on stains that are either protein- or starch-based, such as those caused by blood, milk, grass or fruit juices.
  • Preferred enzymes are cellulases, proteases, amylases and lipases.
  • Preferred enzymes are cellulases and proteases, especially proteases.
  • Cellulases are enzymes which act on cellulose and its derivatives and hydrolyze them into glucose, cellobiose, cellooligosaccharide. Cellulases remove dirt and have the effect of mitigating the roughness to the touch.
  • enzymes to be used include, but are by no means limited to, the following: proteases as given in US-B-6,242,405, column 14, lines 21 to 32; lipases as given in US-B-6,242,405, column 14, lines 33 to 46; amylases as given in US-B-6, 242,405, column 14, lines 47 to 56; and cellulases as given in US-B-6,242,405, column 14, lines 57 to 64.
  • the enzymes can optionally be present in the detergent.
  • the enzymes are usually present in an amount of 0.01 -5% by weight, preferably 0.05-5% and more preferably 0.1-4% by weight, based on the total weight of the detergent.
  • Further preferred additives for the detergents according to the invention are polymers that, during the washing of textiles, inhibit staining caused by dyes in the washing liquor that have been released from the textiles under the washing conditions (dye fixing agents, dye transfer inhibitors).
  • Such polymers are preferably polyvinylpyrrolidones, polyvinylimidazoles or polyvinylpyridine N-oxides which may have been modified by the incorporation of anionic or cationic substituents, especially those having a molecular weight in the range from 5000 to 60 000, more especially from 10 000 to 50 000.
  • Such polymers are usually used in an amount of from 0.01 to 5 %, preferably 0.05 to 5 % by weight, especially 0.1 to 2 % by weight, based on the total weight of the detergent.
  • Preferred polymers are those given in WO-A-02/02865 (see especially page 1 , last paragraph and page 2, first paragraph).
  • the detergents used will usually contain one or more auxiliaries such as soil suspending agents, for example sodium carboxymethylcellulose; salts for adjusting the pH, for example alkali or alkaline earth metal silicates; foam regulators, for example soap; salts for adjusting the spray drying and granulating properties, for example sodium sulphate; perfumes; and also, if appropriate, antistatic and softening agents; such as smectite clays; photobleaching agents; pigments; and/or shading agents.
  • auxiliaries can be present in an amount of, for example, 0.1 to 20% by weight, preferably 0.5 to 10 % by weight, especially 0.5 to 5 % by weight, based on the total weight of the detergent.
  • the detergent compositions can take a variety of physical forms including powder, granular, tablet and liquid forms. Examples thereof are conventional powder heavy-duty detergents, compact and supercompact heavy-duty detergents and tablets, like heavy-duty detergent tablets.
  • One important physical form is the so-called concentrated granular form adapted to be added to a washing machine.
  • compact detergents Of importance are also the so-called compact (or supercompact) detergents.
  • compact detergents In the field of detergent manufacture, a trend has developed recently towards the production of compact detergents which contain increased amounts of active substance. In order to minimize energy expenditure during the washing process, the compact detergents are required to operate efficiently at temperatures as low as 40°C, or even at room temperatures, e.g. at 25°C.
  • Such detergents usually contain only low amounts of fillers or processing aids, like sodium sulfate or sodium chloride.
  • the amount of such fillers is usually 0-10% by weight, preferably 0-5 % by weight, especially 0-1 % by weight, based on the total weight of the detergent.
  • Such detergents usually have a bulk density of 650-1000 g/l, preferably 700- 1000 g/l and especially 750-1000 g/l.
  • the detergents can also be present in the form of tablets. Relevant characteristics of tablets are ease of dispensing and convenience in handling. Tablets are the most compact delivery of solid detergents and have a bulk density of, for example, 0.9 to 1.3 kg/litre. To enable fast disintegration laundry detergent tablets generally contain special disintegrants:
  • the tablets can also contain combinations of any of the above disintegrants.
  • the detergent may also be formulated as a an aqueous liquid comprising 5-50, preferably 10-35% water or as a non-aqueous liquid detergent, containing not more than 5, preferably 0-1 wt.% of water.
  • Non-aqueous liiquid detergent compositions can contain other solvents as carriers.
  • Low molecular weight primary or secondary alcohols exemplified by methanol, ethanol, propanol, and isopropanol are suitable.
  • Monohydric alcohols are preferred for solubilizing surfactant, but polyols such as those containing from 2 to about 6 carbon atoms and from 2 to about 6 hydroxy groups (e.g., 1 ,3-propanediol, ethylene glycol, glycerine, and 1 ,2-propanediol) can also be used.
  • the compositions may contain from 5% to 90%, typically 10% to 50% of such carriers.
  • the detergents can also be present as the so-called "unit liquid dose" form.
  • This detergent treatment of textiles can be conducted as a domestic treatment in normal washing machines.
  • the textile fibres treated may be natural or synthetic fibres or mixtures thereof.
  • natural fibres include vegetable fibres such as cotton, viscose, flax, rayon or linen, preferably cotton and animal fibres such as wool, mohair, cashmere, angora and silk, preferably wool.
  • Synthetic fibres include polyester, polyamide and polyacrylonitrile fibres.
  • Preferred textile fibres are cotton, polyamide and wool fibres, especially cotton fibres.
  • textile fibres treated according to the method of the present invention have a density of less than 200 g/m 2 .
  • the process is usually conducted in the temperature range of from 5 to 100°C, especially 5 to 60°C.
  • Preferred is a temperature range of 5 to 40°C, especially 5 to 35°C and more preferably 5 to 30°C.
  • the detergent compositions herein will preferably be formulated such that, during use in aqueous cleaning operations, the wash water will have a pH of between about 6.5 and about 11 , preferably between about 7.5 and 11. Laundry products are typically at pH 9-11. Techniques for controlling pH at recommended usage levels include the use of buffers, alkalis, acids, etc., and are well known to those skilled in the art.
  • Machine laundry methods herein typically comprise treating soiled laundry with an aqueous wash solution in a washing machine having dissolved or dispensed therein an effective amount of a machine laundry detergent composition in accordance with the invention.
  • an effective amount of the detergent composition it is meant, e.g., from 20 g to 300 g of product dissolved or dispersed in a wash solution of volume from 5 to 85 litres, as are typical product dosages and wash solution volumes commonly employed in conventional machine laundry methods. Examples are
  • the liquor ratio is preferably 1 :4 to 1 :40, especially 1 :4 to 1 :15. Highly preferred is a liquor ratio of 1 :4 to 1 :10, especially 1 :5 to 1 :9.
  • a further object of the present invention is to provide a process for the domestic washing treatment of a textile fibre material wherein the textile fibre material is contacted with an aqueous solution of a detergent comprising a compound of formula (1) as defined above, and wherein the detergent contains a peroxide, a peroxide activator and/or a bleaching catalyst, and wherein the temperature of the solution is between 5°C and 40°C, preferably between
  • the definitions and preferences given above apply.
  • the compounds used according to the present invention are particularly advantageous in that they exhibit not only extremely high whitening ability, but, in addition, in many cases highly desirable water solubilities and also possess excellent white aspects in the solid state.
  • a further advantage of the present invention is that the detergent composition delivers improved whiteness performance and fabric feel. Furthermore the compounds show very good results with respect to exhaustion properties.
  • the compounds have the advantage that they are also effective in the presence of active chlorine donors, such as, for example, hypochlorite and can be used without substantial loss of the effects in washing baths with non-ionic washing agents, for example alkylphenol polyglycol ethers.
  • active chlorine donors such as, for example, hypochlorite
  • non-ionic washing agents for example alkylphenol polyglycol ethers.
  • perborate or peracids and activators for example tetraacetylglycoluril or ethylenediamine-tetraacetic acid are the compounds stable both in pulverulent washing agent and in washing baths. In addition, they impart a brilliant appearance in daylight.
  • Na + are mixed with 600ml of water and heated to a temperature of 60°C. Then 9.2g of 2- ethylaminoethanol are added and the reaction mixture is heated to a temperature of 98°C; during heating the pH is maintained at a value between 8.5 and 9 by addition of a 4-molar aqueous solution of sodium hydroxide. The reaction mixture is cooled to 50°C and the pH is adjusted to a value of 4.5 by addition a 6-molar aqueous solution of hydrochloric acid. The precipitate is filtered off, washed with 100ml of a 10% aqueous sodium chloride solution and dried in vacuum. In this way, there are obtained 30.5g of a yellowish product.
  • Na + can be prepared in analogy to the process given in Preparation Example 1 , by replacing 9.2 g of 2-ethylaminoethanol with an equimolar amount of the corresponding amine.
  • X is as defined in the following Table 1. Compounds which precipitate after cooling to 50°C are isolated directly as sodium salts without addition of hydrochloric acid and then dried in vaccuum.
  • Na can be prepared in analogy to the process given in Preparation Example 16, by replacing 9.5 g of morpholine with an equimolar amount of the corresponding amine.
  • X is as defined in the following Table 2.
  • Compounds having high solubility are treated with a 6-molar aqueous solution of hydrochloric acid in order to adjusted the pH to a value of 4.5 before cooling to 50°C.
  • Table 2
  • the compound of formula (107) can be prepared in analogy to the process given in Preparation Example 21 , by replacing 15 g of an aqueous solution of ethylamine (70%) with a corresponding solution containing an equimolar amount of diethylamine.
  • a wash liquor is prepared by dissolving 0.8 g of a washing powder in 200 ml of tap water. 10 g of bleached cotton fabric is added to the bath and washed at 40°C over 15 minutes and then rinsed, spin-dried and ironed at 160°C.
  • washing powders A and B are used (amounts given in the following Tables 3a and 3b are in g):
  • a wash liquor is prepared by dissolving 0.8 g of a washing powder in 200 ml of tap water. 10 g of bleached cotton fabric is added to the bath and washed at 30°C over 15 minutes and then rinsed, spin-dried and ironed at 160°C.
  • washing powders are used (amounts given in the following Tables 4a and 4b are percent by weight, based on the total weight of the detergent):

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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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cleaning By Liquid Or Steam (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP03706527A 2002-02-25 2003-02-18 Prozess zum behandeln von textilen fasermaterialien Expired - Lifetime EP1478724B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP06118810A EP1724333A1 (de) 2002-02-25 2003-02-18 Prozess zum Behandeln von textilen Fasermaterialien
EP03706527A EP1478724B1 (de) 2002-02-25 2003-02-18 Prozess zum behandeln von textilen fasermaterialien

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
EP02405136 2002-02-25
EP02405136 2002-02-25
EP02405876 2002-10-11
EP02405876 2002-10-11
PCT/EP2003/001619 WO2003070870A1 (en) 2002-02-25 2003-02-18 Process for the treatment of textile fibre materials
EP03706527A EP1478724B1 (de) 2002-02-25 2003-02-18 Prozess zum behandeln von textilen fasermaterialien

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP06118810A Division EP1724333A1 (de) 2002-02-25 2003-02-18 Prozess zum Behandeln von textilen Fasermaterialien

Publications (2)

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EP1478724A1 true EP1478724A1 (de) 2004-11-24
EP1478724B1 EP1478724B1 (de) 2006-09-20

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EP03702652A Expired - Lifetime EP1485460B1 (de) 2002-02-25 2003-02-18 Prozess zur behandlung von textilen fasermaterialien
EP03706527A Expired - Lifetime EP1478724B1 (de) 2002-02-25 2003-02-18 Prozess zum behandeln von textilen fasermaterialien
EP06118792.8A Expired - Lifetime EP1715029B1 (de) 2002-02-25 2003-02-18 Prozess zur Behandlung von textilen Fasermaterialien
EP06118810A Withdrawn EP1724333A1 (de) 2002-02-25 2003-02-18 Prozess zum Behandeln von textilen Fasermaterialien

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EP06118810A Withdrawn EP1724333A1 (de) 2002-02-25 2003-02-18 Prozess zum Behandeln von textilen Fasermaterialien

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EP (4) EP1485460B1 (de)
JP (2) JP4567976B2 (de)
CN (2) CN1294247C (de)
AR (3) AR038582A1 (de)
AT (2) ATE340242T1 (de)
AU (2) AU2003205777B2 (de)
BR (3) BR0306184B1 (de)
DE (2) DE60308485T2 (de)
ES (3) ES2556971T3 (de)
TW (2) TWI332045B (de)
WO (2) WO2003070870A1 (de)
ZA (2) ZA200402941B (de)

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WO2004085594A1 (en) 2003-03-24 2004-10-07 Ciba Specialty Chemicals Holding Inc. Detergent compositions
CN100478431C (zh) 2004-01-20 2009-04-15 西巴特殊化学品控股有限公司 三嗪基氨基茋二磺酸混合物
WO2005103220A1 (en) * 2004-04-20 2005-11-03 Ciba Specialty Chemicals Holding Inc. Amphoteric fluorescent whitening agents in detergent formulations
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CN109158366B (zh) * 2014-01-26 2021-08-24 艺康美国股份有限公司 原位清洗工艺和原位清洗系统
WO2015113141A1 (en) 2014-01-31 2015-08-06 Goldcorp Inc. Process for separation of at least one metal sulfide compristng arsenic and/or antimony from a mixed sulfide concentrate
CN105001671A (zh) * 2015-06-29 2015-10-28 纳爱斯丽水日化有限公司 一种复合型增白剂及含所述增白剂的洗涤剂组合物
CN107857738A (zh) * 2017-11-28 2018-03-30 贺州学院 十六烷基氨基三嗪衍生物的合成与应用

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EP1485460B1 (de) 2006-09-27
CN1596300A (zh) 2005-03-16
DE60308661D1 (de) 2006-11-09
ES2271529T3 (es) 2007-04-16
BRPI0306187B1 (pt) 2021-01-12
ES2271534T3 (es) 2007-04-16
EP1715029B1 (de) 2015-09-23
AU2003208870A1 (en) 2003-09-09
JP2005517801A (ja) 2005-06-16
AR067835A2 (es) 2009-10-28
EP1715029A2 (de) 2006-10-25
TWI324177B (en) 2010-05-01
ZA200402942B (en) 2005-02-23
AR038583A1 (es) 2005-01-19
TWI332045B (en) 2010-10-21
CN1294248C (zh) 2007-01-10
BR0306184B1 (pt) 2013-08-27
EP1724333A1 (de) 2006-11-22
AR038582A1 (es) 2005-01-19
CN1596299A (zh) 2005-03-16
WO2003070869A1 (en) 2003-08-28
JP4567975B2 (ja) 2010-10-27
ATE340242T1 (de) 2006-10-15
BR0306184A (pt) 2004-10-19
DE60308485D1 (de) 2006-11-02
ZA200402941B (en) 2005-02-23
AU2003208870B2 (en) 2008-05-15
ATE340847T1 (de) 2006-10-15
EP1478724B1 (de) 2006-09-20
AU2003205777A1 (en) 2003-09-09
AU2003205777B2 (en) 2008-01-31
JP4567976B2 (ja) 2010-10-27
TW200303386A (en) 2003-09-01
WO2003070870A1 (en) 2003-08-28
DE60308661T2 (de) 2007-08-09
EP1715029A3 (de) 2009-04-01
EP1485460A1 (de) 2004-12-15
DE60308485T2 (de) 2007-09-06
BR0306187A (pt) 2004-10-19
TW200303358A (en) 2003-09-01
CN1294247C (zh) 2007-01-10
JP2005517800A (ja) 2005-06-16
ES2556971T3 (es) 2016-01-21

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