EP1105366A1 - Derives d'acide divinylstilbenesulfonique - Google Patents

Derives d'acide divinylstilbenesulfonique

Info

Publication number
EP1105366A1
EP1105366A1 EP99938372A EP99938372A EP1105366A1 EP 1105366 A1 EP1105366 A1 EP 1105366A1 EP 99938372 A EP99938372 A EP 99938372A EP 99938372 A EP99938372 A EP 99938372A EP 1105366 A1 EP1105366 A1 EP 1105366A1
Authority
EP
European Patent Office
Prior art keywords
formula
compound
alkyl
hydrogen
cyano
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.)
Ceased
Application number
EP99938372A
Other languages
German (de)
English (en)
Inventor
Victor Paul Eliu
Peter Rohringer
Julia Hauser
Hans Kramer
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 EP99938372A priority Critical patent/EP1105366A1/fr
Publication of EP1105366A1 publication Critical patent/EP1105366A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
    • C07C309/32—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings containing at least two non-condensed six-membered aromatic rings in the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C07C309/58—Carboxylic acid groups or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C07C309/59—Nitrogen analogues of carboxyl groups
    • 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
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
    • 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
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3427—Organic compounds containing sulfur containing thiol, mercapto or sulfide groups, e.g. thioethers or mercaptales
    • 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
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • 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

Definitions

  • the present invention relates to divinylstilbenesulfonic acid derivatives, to a process for the preparation of these compounds and to their use as fluorescent whitening agents.
  • the divinylstilbenesulfonic acid derivatives of this invention correspond to formula
  • Yi and Y 2 are each independently of the other hydrogen or -SO 3 " M + ; at least one Y, or Y 2 being -SO 3 " M + ;
  • Ri is hydrogen; C C 18 alkyl or C -C 18 alkenyl which is unsubstituted or substituted by cyano, -SH, d-Csalkylthio, C C 5 alkoxy, amino, d-dmonoalkylamino, C C 5 dialkyl- amino or carboxy; mono-, di- or trihydroxy-d-C 5 alkyl; a radical of formula
  • phenyl-C ⁇ -C 3 alkyl which is unsubstituted or substituted by one or several C r C 5 alkyl, d-C 5 alkoxy, hydroxy, cyano, sulfo or halogen;
  • R 2 and R 3 are each independently of the other hydrogen; C C 5 alkyl which is unsubstituted or substituted by cyano, -SH, CrC 5 alkylthio, C C 5 alkoxy or carboxy; hydroxy-CrC 5 alkyl; mono- or di-d-Csalkylamino-d-Csalkyl; phenyl or phenyl-d-C 3 alkyl which is unsubstituted or substituted by one or several C C 5 alkyl, C dalkoxy,hydroxy, cyano, sulfo or halogen; or
  • R 2 and R 3 together with the linking nitrogen atom, are a five- or six-membered heterocyclic radical
  • FU is hydrogen, d-C 5 alkyl, Ci-Csalkoxy, hydroxy, cyano, sulfo or halogen
  • M is hydrogen; an alkali metal cation or alkaline earth metal cation; or a cation formed from an amine
  • mi is a number from 1 to 5
  • n ! is a number from 1 to 3.
  • d-d ⁇ Alkyl is a straight-chain or branched radical, for example methyl, ethyl, n-propyl, iso- propyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl.
  • d-CsAlkyloxy or C ⁇ -C 5 alkylthio is a straight-chain or branched radical, for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy or methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio or amylthio.
  • C 2 -Ci 8 Alkenyl is, for example, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n- penta-2,4-dienyl, 3-methylbut-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-dodec-2- enyl or n-octadec-4-enyl.
  • Examples of d-C 5 monoalkylamino or Ci-Csdialkylamino are methylamino, ethylamino, pro- pylamino, butylamino, tert-butylamino or dimethylamino, diethylamino, methylethylamino, dipropylamino, dibutylamino or di-tert-butylamino.
  • substituent pair (R 2 and R 3 ), together with the linking nitrogen atom is a heterocyclic radical
  • this radical is, for example, pyrrolidino, piperidino, pipecolino, morpholino, thio- morpholino, piperazino, N-alkylpiperazino, such as N-methylpiperazino, N-phenylp ' perazino or N-alkylimidazolino.
  • Preferred saturated heterocyclic radicals used for -NR 2 R 3 are pyrrolidino, piperidino or morpholino.
  • Suitable compounds of formula (1 ) are preferably those, wherein
  • Ri is hydrogen; hydroxy; C C 5 alkyl; d-C 5 hydroxyalkyl; amino or a radical of formula (1 a); particularly preferably compounds of formula (1), wherein Ri is d-C 3 alkyl and, very particularly, methyl or ethyl.
  • Ri is a radical of formula -O-(CH 2 ) 2 -O-(CH 2 ) 2 -O-(CH 2 )2-OH.
  • R 2 and R 3 are each independently of the other hydrogen; mono- or di-C r C 5 alkylamino-C ⁇ -
  • R 2 and R 3 together with the linking nitrogen atom, are a mo ⁇ holino radical.
  • the inventive divinylstilbenesulfonic acid derivatives are prepared in a manner known per se by diazotising the corresponding aminostilbene compound of formula
  • X, Yi, Y 2 are as defined for formula (1).
  • X ' is a counterion.
  • Suitable diazotisation reagents are alkyl nitrite, nitrosylsulfuric acid and, preferably, sodium nitrite.
  • the temperature in this reaction step is in the range from 0 to 90°C, preferably from 10 to 40°C.
  • the diazotisation is preferably carried out in the presence of a mineral acid, for example sulfuric acid, methanesulfonic acid or tetrafluoroboric acid.
  • a mineral acid for example sulfuric acid, methanesulfonic acid or tetrafluoroboric acid.
  • the diazonium compound so obtained e.g. sodium acetate, sodium bicarbonate or sodium carbonate is used as a base.
  • the reaction of the diazonium compound with the acryl compound of formula (15) is preferably carried out in the presence of a catalyst.
  • the reaction can be carried out in aqueous or anhydrous medium.
  • Suitable non-aqueous solvents are alcohols, for example pentyl alcohol, acetic acid, dimethylformamide, N-methyl- pyrrolidone, dimethylacetamide, glycol ether, acetonitrile or DMSO.
  • the reaction can also be carried out in two-phase systems, for example mixtures consisting of water and halogenated hydrocarbons and dichloromethane or pentyl alcohol and phase transfer catalysts.
  • the inventive divinylstilbenesulfonic acid derivatives are usually used to optically brighten synthetic or natural organic materials.
  • textile fibres such as those consisting of synthetic poly- amides or of natural fibres of animal or vegetable origin based on cellulose or protein, for example cotton, wool, linen, silk or paper.
  • the textile materials can be in different forms of presentation and are preferably piece goods, such as wovens or knitgoods, or yarn on cheeses, warp beams, and the like.
  • the divinylstilbenesulfonic acid derivatives of this invention can be inco ⁇ orated for optical brightening in liquid and solid detergents, application liquors or paper coating compositions.
  • the formulations so obtained can additionally contain the conventional formulation assistants, such as dispersants, builders, protective colloids, stabilisers, preservatives, perfumes, pigments, enzymes and sequestrants.
  • conventional formulation assistants such as dispersants, builders, protective colloids, stabilisers, preservatives, perfumes, pigments, enzymes and sequestrants.
  • Dispersants used are preferably nonionic dispersants, e.g. fatty alcohols, ethoxylation products of fatty alcohols or fatty acids, or anionic dispersants, such as the condensates of aromatic sulfonic acids with formaldehyde, for example those based on ditolyl ether sulfonic acids, naphthalene sulfonates or lignin sulfonates.
  • nonionic dispersants e.g. fatty alcohols, ethoxylation products of fatty alcohols or fatty acids
  • anionic dispersants such as the condensates of aromatic sulfonic acids with formaldehyde, for example those based on ditolyl ether sulfonic acids, naphthalene sulfonates or lignin sulfonates.
  • Suitable builders or protective colloids are, for example, modified polysaccharides which are derived from cellulose, or heteropolysaccharides, such as xanthan, ca ⁇ oxymethylcellulose and also aluminium silicates or magnesium silicates. Additional stabilisation assistants which may be added are, for example, ethylene glycol, propylene glycol and further dispersants.
  • Preservatives used are, for example, compounds such as 1 ,2-benzisothiazolin-3-one, formaldehyde or chloroacetamide.
  • this invention also relates to a process for improving the SPF-value of textile fibre materials.
  • This process comprises treating the fibre material with 0.05 to 3 % by weight, based on the weight of the fibre material, of one or several of the compounds of formula (1).
  • the fibre material treated by the inventive process preferably has a density of less than 200 g/cm 2 and is as a rule dyed in pastel shades before treatment.
  • reaction mixture is separated by suction filtration, about 66 g of filter product being obtained.
  • This filter product is then dried under vacuum and recrystallised from water, resulting in 24.5 g of the compound of formula (101).
  • acetic anhydride 60 g are added dropwise to reduce the water concentration, the temperature being kept below 20°C by cooling. After stirring the mixture for 20 minutes, 16.8 g of sodium hydrogencarbonate are slowly added, the foam formation being controlled. 0.3 g of palladium dibenzylacetone and 8.0 g of acrylamide are stirred in. The reaction starts immediately with vigorous degassing. The temperature rises to 40°C over about 2 to 3 hours. If the diazo component test is negative, the mixture is worked up using the conventional methods.
  • reaction mixture is separated by suction filtration, about 50 g of filter product being obtained.
  • This filter product is dried under vacuum and recrystallised from water, resulting in 21.5 g of the compound of formula (102).
  • acetic anhydride 50 g of acetic anhydride are added dropwise to reduce the water concentration, the temperature being kept below 20°C by cooling. After stirring the mixture for 20 minutes, 10.8 g of sodium carbonate are slowly added, the foam formation being controlled. 0.3 g of palladium dibenzylacetone and 10.0 g of methyl acrylate are stirred in. The reaction starts immediately with vigorous degassing. The temperature rises to 35°C over about 2 to 3 hours. If the diazo component test is negative, the mixture is worked up using the conventional methods.
  • reaction mixture is separated by suction filtration, about 70 g of filter product being obtained.
  • This filter product is dried under vacuum and recrystallised from water, resulting in 18.5 g of the compound of formula (103).
  • acetic anhydride 60 g are added dropwise to reduce the water concentration, the temperature being kept below 20°C by cooling. After stirring the mixture for 20 minutes, 16.8 g of sodium hydrogencarbonate are slowly added, the foam formation being controlled. 0.3 g of palladium chloride solution, about 20% in hydrochloric acid, and 12.2 g of hydroxyethyl acrylate are stirred in. The reaction starts immediately with vigorous degassing. The temperature rises to 50°C over about 2 to 3 hours. If the diazo component test is negative, the mixture is worked up by the conventional methods.
  • reaction mixture is separated by suction filtration, about 110 g of filter product being obtained.
  • This filter product is dried under vacuum, about 36 g of crude product remaining, and recrystallised from water and sodium chloride, resulting in 20.0 g of the compound of formula (104).
  • acetic anhydride 60 g are added dropwise to reduce the water concentration, the temperature being kept below 20°C with cooling. After stirring the mixture for 20 minutes, 16.8 g of sodium hydrogencarbonate are slowly added, the foam formation being controlled. 0.3 g of palladium dibenzylacetone and 8.0 g of acrylic acid are stirred in. The reaction starts immediately with vigorous degassing. The temperature rises to 40°C over about 2 to 3 hours. If the diazo component test is negative, the mixture is worked up using the conventional methods.
  • the starting material used for this compound is the ethyl ester prepared according to Example 1 (compound of formula (101)).24.5 g of the dry, ground compound are suspended in 150 g of triethylene glycol and then 1 g of sodium ethoxide is added and the mixture is stirred for six hours at 80-90°C and 20 mbar, the resulting ethanol being removed by distillation. This gives a clear solution containing 34 g of the triethylene glycol ester of formula (105).
  • the starting material used for this compound is the ethyl ester prepared according to Example 1 (compound of formula (101)). 24.5 g of the dry compound are suspended in 150 g of diethanolamine and then 1 g of sodium ethoxide is added and the mixture is stirred for eight hours at 100°C and 20 mbar, the resulting ethanol being removed by distillation. This gives a clear solution containing 30 g of diethanolamide of formula (107).
  • the starting material used for this compound is the ethyl ester prepared according to Example 1 (compound of formula (101)).
  • 24.5 g of the dry, ground compound are suspended in 250 g of mo ⁇ holine and then 1 g of sodium ethoxide is added and the mixture is stirred for six hours at 100°C and 200 mbar, the resulting ethanol being removed by distillation.
  • the mo ⁇ holine is removed by distillation under a vacuum of 40 mbar, 34 g of bis-morpholinamide of formula (108) being obtained.
  • the starting material used for this compound is the ethyl ester prepared according to Example 1 (compound of formula (101)).
  • 24.5 g of the dry, ground compound are suspended in 250 g of diethylaminoethylamine.
  • 1 g of sodium ethoxide is added and the mixture is stirred for 10 hours at 100°C and 200 mbar, the resulting ethanol being removed by distillation.
  • the diethylaminoethylamine is removed by distillation under a vacuum of 40 mbar, affording 30 g of bis-diethylaminoethylamide of formula (109).
  • the starting material used for this compound is the free acid prepared according to Example 5 (compound of formula (105)). 18.0 g of the dry, ground compound are suspended in 150 g of thionyl chloride and the suspension is reacted, with stirring, at 70°C. After abundant degassing, the reaction mixture is concentrated by evaporation. The mixture is then suspended in 250 g of DMSO and then 17.5 g of orthanilic acid sodium salt and 10 g of sodium carbonate are added. This mixture is stirred for 4 hours at 60°C.
  • the starting material used for this compound is the amide prepared according to Example 2 (compound of formula (102)). 21.5 g of dry, ground material are suspended in 150 g of phosphorus oxychloride and the suspension is stirred for 3 hours at 70°C. After the reaction is complete, the mixture is separated by removing the acid chloride by distillation. The distillation residue is slurried in ice water, separated by filtration and dried, resulting in 17 g of the nitrile of formula (111).
  • IR abso ⁇ tion at 1670 cm '1 , the carbonyl group disappears and an IR band appears at 2105 cm "1 which can be assigned to the nitrile group.
  • acetic anhydride 60 g of acetic anhydride are added dropwise to reduce the water concentration, the temperature being kept below 20°C by cooling. After stirring the mixture for 20 minutes, 16.8 g of sodium hydrogencarbonate are slowly added, the foam formation being controlled. 0.3 g of palladium chloride solution (c. 20%) in hydrochloric acid and 14.2 g of butyl acrylate are stirred in. The reaction starts immediately with vigorous degassing. The temperature rises to 50°C over about 2 to 3 hours. If the diazo component test is negative, the mixture is worked up.
  • reaction mixture is separated by suction filtration, resulting in about 110 g of filter product.
  • This filter product is dried under vacuum, about 38 g of crude product remaining, and is recrystallised from water and sodium chloride, resulting in 28.0 g of the compound of formula (112).
  • acetic anhydride 60 g of acetic anhydride are added dropwise to reduce the water concentration, the temperature being kept below 20°C by cooling. After stirring the mixture for 20 minutes, 16.8 g of sodium hydrogencarbonate are slowly added, the foam formation being controlled. 0.3 g of palladium chloride solution (c. 20%) in hydrochloric acid and 29.4 g of lauryl acrylate are then stirred in. The reaction starts immediately with vigorous degassing. The temperature rises to 50°C over about 4 to 5 hours. If the diazo component test is negative, the mixture is worked up.
  • reaction mixture is separated by suction filtration, about 140 g of filter product being obtained.
  • This filter product is dried under vacuum, about 50 g of crude product remaining, and is recrystallised from water and sodium chloride, resulting in 30.0 g of the compound of formula (113).
  • the starting material used for this compound is the ethyl ester prepared according to Example 1 (compound of formula (101)).
  • 24.5 g of the dry, ground compound are suspended in 500 g of allyl alcohol and then 1 g of sodium ethoxide is added and the mixture stirred for 10 hours at 90-98°C under normal pressure, the resulting ethanol being removed by distillation by means of a rectification column.
  • the suspension of transesterified product is separated by filtration and dried, resulting in 34 g of allyl diester of formula (114).
  • the yellow reaction mixture is separated by suction filtration, about 300 g of filter product being obtained.
  • This filter product is dried under vacuum and recrystallised from methanol, resulting in 120 g of the compound of formula (115).
  • the compounds listed in Table 1 are dissolved in deionised water and are added to the paper pulp at a consistency of 2.2 %. The subsequent exhaustion time is 15 minutes. The retention agent is added shortly before sheet forming and the paper samples are dried under vacuum at 80°C (System Rapid Koethen).
  • a Spectroflash 500 is used to measure the brightness (ISO) and to calculate the difference between the brightness of a specimen with and without treatment. The results are listed as fluorescence (ISO) in Table 1:
  • Example 17 Use in a size press
  • the compounds listed in Table 3 are admixed in a concentration of 0.1% to a commercially available liquid detergent without fluorescent whitening agent and containing the following ingredients in accordance with EG recommendation: ⁇ 5% phosphonates, cationic surfactants
  • a washing liquor is prepared consisting of 0.4 g of the above detergent in 50 ml of drinking water.
  • the whiteness of the fabric is then determined by means of a DCI/SF 500 spectrophoto- meter by the Ganz method:
  • the mixture is applied to 5 g of bleached cotton and 5 g of polyamide by the pad-batch process (liquor uptake 70%).
  • the fabric samples are dried at 60 °C and are then thermofixed for 3 minutes at 160 °C.
  • the whiteness of the fabric is then determined by means of a DCI/SF 500 spectrophoto- meter by the Ganz method: Table 4
  • Example 20 Use in textile application; exhaust process
  • the compounds listed in Table 5 are dissolved and applied to cotton and polyamide by the pad-batch process as described in Example 19.
  • the cotton fabric samples are then immediately placed in 200 ml of a liquor comprising 10 g/l of sodium sulfate.
  • the polyamide fabric samples are placed in 200 ml of a liquor which is buffered at pH 7 by means of a phosphate buffer.
  • the two liquors are heated from 25 °C to 100 °C over 35 minutes and are kept at 100°C for 30 minutes. Subsequently, the liquors are cooled to room temperature. The fabric samples are rinsed, spin-dried and ironed at 160°C.
  • the whiteness of the fabric is determined by means of a DCI/SF 500 spectrophotometer by the Ganz method:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Dérivés d'acide divinylstilbènesulfonique représentés par la formule (1) dans laquelle X est (a); (b); -CN; ou (c); Y1 et Y2 représentent chacun indépendamment hydrogène ou -SO3-M+; au moins un Y¿1? ou Y2 représentant -SO3?-M+; R¿1 représente hydrogène; alkyle C1-C18 ou alkényle C2-C18 non substitué ou substitué par cyano, -SH, alkythio C1-C5, alkoxy C1-C5, amino, monoalkylamino C1-C5, dialkylamino C1-C5 ou carboxy; mono-, di- ou trihydroxyalkyle C1-C5; un radical représenté par la formule (1a), amino; monoalkylamino C1-C5; dialkylamino C1-C5; phényle ou phénylalkyle C1-C3 non substitué ou substitué par un ou plusieurs alkyle C1-C5, alkoxy C1-C5, hydroxy, cyano, sulfo ou halogène; R2 et R3 représentent chacun indépendamment hydrogène, alkyle C1-C5 non substitué ou substitué par cyano, -SH, alkylthio C1-C5, alkoxy C1-C5 ou carboxy; hydroxyalkyle C1-C5; mono- ou dialkylamino C1-C5 alkyle C1-C5; phényl ou phénylalkyle C1-C3 non substitué ou substitué par un ou plusieurs alkyle C1-C5, alkoxy C1-C5, hydroxy, cyano, sulfo ou halogène; ou R2 et R3 avec l'atome d'azote de liaison, représentent un radical hétérocyclique à cinq ou six éléments; R4 représente hydrogène, alkyle C1-C5, alkoxy C1-C5, hydroxy, cyano, sulfo ou halogène; M représente hydrogène; un cation de métal alcalin ou un cation de métal terreux alcalin; ou un cation constitué à partir d'une amine; m1 est un nombre de 1 à 5; et n1 est un nombre de 1 à 3. On utilise ces composés afin d'amplifier la brillance optique de matériaux organiques synthétiques ou naturels.
EP99938372A 1998-08-10 1999-07-29 Derives d'acide divinylstilbenesulfonique Ceased EP1105366A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP99938372A EP1105366A1 (fr) 1998-08-10 1999-07-29 Derives d'acide divinylstilbenesulfonique

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP98810763 1998-08-10
EP98810763 1998-08-10
PCT/EP1999/005431 WO2000009471A1 (fr) 1998-08-10 1999-07-29 Derives d'acide divinylstilbenesulfonique
EP99938372A EP1105366A1 (fr) 1998-08-10 1999-07-29 Derives d'acide divinylstilbenesulfonique

Publications (1)

Publication Number Publication Date
EP1105366A1 true EP1105366A1 (fr) 2001-06-13

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EP (1) EP1105366A1 (fr)
AU (1) AU5289299A (fr)
WO (1) WO2000009471A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001092217A2 (fr) * 2000-05-30 2001-12-06 Ciba Specialty Chemicals Holding Inc. Procede pour la preparation de composes d'acide amidostyrylstilbene-disulphonique
WO2002055488A1 (fr) * 2001-01-12 2002-07-18 Ciba Specialty Chemicals Holdings Inc. Acides divinylstilbene-sulphoniques asymetriques
KR101408026B1 (ko) * 2005-12-02 2014-06-20 사켐,인코포레이티드 음이온-교환 치환 크로마토그래피 공정 및 음이온-교환치환 크로마토그래피 공정에서 디스플레이서 화합물들로서사용하기 위한 음이온성 유기 화합물들
CN110922531B (zh) * 2019-12-06 2022-06-24 陕西科技大学 一种淀粉接枝荧光共聚乳液及其制备方法与应用

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