WO2001044210A1 - Derives allyl- et diallylaminotriazinylaminostilbene et leur utilisation en tant qu'azureur optique - Google Patents

Derives allyl- et diallylaminotriazinylaminostilbene et leur utilisation en tant qu'azureur optique Download PDF

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Publication number
WO2001044210A1
WO2001044210A1 PCT/EP2000/012200 EP0012200W WO0144210A1 WO 2001044210 A1 WO2001044210 A1 WO 2001044210A1 EP 0012200 W EP0012200 W EP 0012200W WO 0144210 A1 WO0144210 A1 WO 0144210A1
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WIPO (PCT)
Prior art keywords
alkyl
formula
compound
substituted
phenylamino
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PCT/EP2000/012200
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English (en)
Inventor
Bernd Wockenfuss
Hans Kramer
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Ciba Specialty Chemicals Holding Inc.
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.)
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Publication date
Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.
Priority to AU30062/01A priority Critical patent/AU3006201A/en
Publication of WO2001044210A1 publication Critical patent/WO2001044210A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/68—Triazinylamino stilbenes

Definitions

  • the present invention relates to new allyl- and diallylaminotriazinylaminostilbene derivatives which are useful as optical brightening agents for synthetic or natural organic materials.
  • novel salts of allyl- and diallyiaminotriazinylamino- stilbenes are useful as optical brightening agents for paper, textile and detergent applications, possessing superior properties with regard to, for example, solubility, light- fastness and degree of whiteness.
  • Ri represents, independently, an allyl- or diallylamino residue
  • R represents, independently, phenylamino which is unsubstituted or substituted by one or more C,-C 4 -aikyl, halogen, cyano, S0 3 M, -S0 2 NH 2 , S0 2 NHC ⁇ -C 4 -alkyl, -C0 2 M, -C0 2 C 1 -C4-al yl, -CONH 2 , -CONHd-C-4-alkyl, or -NHCOCrC 4 -alkyl groups, with the proviso that the phenylamino group is not substituted by two S0 3 Na groups; or an allyl- or diallylamino residue and M is an alkali or alkaline-earth metal atom, ammonium or a cation formed from an amine.
  • both of the R , groups and the R 2 groups are preferably identical.
  • Preferred compounds of formula (1) are those in which R 2 represents phenylamino, optionally substituted by a C ⁇ -C 4 -alkyl, halogen, cyano, S0 3 M, -SO 2 NH 2 , SO 2 NHC 1 -C 4 -alkyl, -C0 2 M, -C0 2 Ci-C 4 -alkyl, -CONH 2 , -CONHC ⁇ -C 4 -alkyl, or -NHCOd-C 4 -alkyl group, especially such in which R 2 represents phenylamino which may be substituted by S0 3 M, M being as previously defined.
  • R ⁇ and R 2 both, independently, represent an allyl- or diallylamino residue.
  • the cation M within the scope of formula (1), is, preferably, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-Crdalkylammonium, mono-, di- or tri-C 2 -C -hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C C 4 -alkyl and C 2 -C 4 -hydroxyalkyl groups.
  • Especially preferred compounds of formula (1) are those in which R ⁇ is allylamino, R 2 is phenylamino which may be unsubstituted or substituted by S0 3 Na and M is Na , as well as those, in which R ⁇ is diallylamino, R 2 is phenylamino which may be unsubstituted or substituted by S0 3 Na, whereby M is Na and, additionally, those in which Ri and R 2 are both allylamino or diallylamino and M is Na.
  • C ⁇ -C 4 alkyl may be methyl, ethyl, n- or isopropyl or n-, sec- or t-butyl and C 2 -C 4 -hydroxyalkyl may be hydroxyethyl, hydroxypropyl or hydroxybutyl, whilst halogen may be fluorine, chlorine, bromine or iodine, preferrably chlorine.
  • the 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, an amino compound capable of introducing a group group R 2 in which R 2 has its previous significance, and a compound capable of introducing a group R ⁇ , in which Ri has its previous significance i.e. allyl- or diallylamine
  • cyanuric chloride Preferably, 2 moles of cyanuric chloride are initially reacted with 1 mole of 4,4'-diaminostilbene-2,2'- disulfonic acid, then with an amino compound capable of introducing a group R 2 in which R 2 has its previous significance, and, finally, with allyl- or diallylamine.
  • the starting materials are known compounds which are readily available.
  • a further aspect of the invention is a composition for whitening synthetic or natural organic materials, which contains water, a fluorescent whitening agent of formula (1) and, optionally, auxiliaries.
  • such brightener compositions contain water and, in each case based on the weight of the formulation, from 3 to 25% by weight, preferably from 5 to 15% by weight of the above defined fluorescent whitening agent mixture and also 0 to 60%, preferably 5 to 50% by weight, of auxiliaries.
  • auxiliaries include, for example, anionic or non-ionic dispersants from the class of ethylene oxide adducts with fatty alcohols, higher fatty acids or alkyl phenols or ethylenediamine ethylene oxide-propylene oxide adducts, copolymers of N-vinylpyrrolidone with 3-vinylpropionic acid, water retention aids, such as ethylene glycol, glycerol orsorbitol, or biocides.
  • anionic or non-ionic dispersants from the class of ethylene oxide adducts with fatty alcohols, higher fatty acids or alkyl phenols or ethylenediamine ethylene oxide-propylene oxide adducts, copolymers of N-vinylpyrrolidone with 3-vinylpropionic acid, water retention aids, such as ethylene glycol, glycerol orsorbitol, or biocides.
  • Most of the compounds of formula (1) are excellent fluorescent whitening agents for substrates such as textiles and for paper and for the addition to detergent compositions.
  • the present invention further provides a method for the fluorescent whitening of a substrate comprising contacting the substrate with a compound having the formula (1).
  • the compound of formula (1) according to the present invention may be applied to the paper substrate in the form of a paper coating composition, or directly in the size press.
  • the present invention provides a method for the fluorescent whitening of a paper surface, comprising contacting the paper surface with a coating composition comprising a white pigment; a binder dispersion; optionally a water-soluble co-binder; and sufficient of a fluorescent whitening agent having the formula (1) according to the present invention, to ensure that the treated paper contains 0.01 to 1 % by weight, based on the white pigment, of a fluorescent whitening agent having the formula (1 ).
  • the white pigment component of the paper coating composition used according to the method of the present invention there are preferred inorganic pigments, e.g., aluminium or magnesium silicates, such as China clay and kaolin and, further, barium sulfate, satin white, titanium dioxide , calcium carbonate (chalk) or talcum; as well as white organic pigments.
  • inorganic pigments e.g., aluminium or magnesium silicates, such as China clay and kaolin and, further, barium sulfate, satin white, titanium dioxide , calcium carbonate (chalk) or talcum; as well as white organic pigments.
  • the paper coating compositions used according to the method of the present invention may contain, as binder, inter alia, plastics dispersions based on copolymers of butadiene/styrene, acrylonitrile/butadiene/styrene, acrylic acid esters, acrylic acid esters/styrene/acrylonitrile, ethylene/vinyl chloride and ethylene/vinyl acetate; or homopolymers, such as polyvinyl chloride, polyvinylidene chloride, polyethylene and polyvinyl acetate or polyurethanes.
  • plastics dispersions based on copolymers of butadiene/styrene, acrylonitrile/butadiene/styrene, acrylic acid esters, acrylic acid esters/styrene/acrylonitrile, ethylene/vinyl chloride and ethylene/vinyl acetate; or homopolymers, such as polyvinyl chloride, polyvinylidene chloride,
  • a preferred binder consists of styrene/butyl acrylate or styrene/butadiene/ acrylic acid copolymers or styrene/butadiene rubbers.
  • Other polymer latices are described, for example, in U.S.Patent Specifications 3,265,654, 3,657,174, 3,547,899 and 3,240,740.
  • the optional water-soluble protective colloid may be, e.g., soya protein, casein, carboxymethylcellulose, natural or modified starch, chitosan or a derivative thereof or, especially, polyvinyl alcohol.
  • the preferred polyvinyl alcohol protective colloid component may have a wide range of saponification levels and molecular weights; e.g. a saponification level ranging from 40 to 100; and an average molecular weight ranging from 10,000 to 100,000. Recipes for coating compositions for paper are described, for example, in J.P. Casey "Pulp and Paper”; Chemistry and Chemical Technology, 2nd edition, Volume III, pagesl 684-1649 and in "Pulp and Paper Manufacture", 2nd and 5th edition, Volume II, page497 (McGraw-Hill).
  • the paper coating compositions used according to the method of the present invention preferably contain 10 to 70% by weight of a white pigment.
  • the binder is preferably used in an amount which is sufficient to make the dry content of polymeric compound up to 1 to 30% by weight, preferably 5 to 25% by weight, of the white pigment.
  • the amount of fluorescent brightener preparation used according to the invention is calculated so that the fluorescent brightener is preferably present in amounts of 0.01 to 1 % by weight, more preferably 0.05 to 1% by weight, and especially 0.05 to 0.6% by weight, based on the white pigment.
  • the paper coating composition used in the method according to the invention can be prepared by mixing the components in any desired sequence at temperature from 10 to 100°C, preferably 20 to 80°C.
  • the components here also include the customary auxiliaries which can be added to regulate the rheological properties, such as viscosity or water retention capacity, of the coating compositions.
  • auxiliaries are, for example, natural binders, such as starch, casein, protein or gelatin, cellulose ethers, such as carboxyalkylcellulose or hydroxyalkylcellulose, alginic acid, alginates, polyethylene oxide or polyethylene oxide alkyl ethers, copolymers of ethylene oxide and propylene oxide, polyvinyl alcohol, water-soluble condensation products of formaldehyde with urea or melamine, polyphosphates or polyacrylic acid salts.
  • natural binders such as starch, casein, protein or gelatin
  • cellulose ethers such as carboxyalkylcellulose or hydroxyalkylcellulose
  • alginic acid alginates
  • polyethylene oxide or polyethylene oxide alkyl ethers copolymers of ethylene oxide and propylene oxide
  • polyvinyl alcohol water-soluble condensation products of formaldehyde with urea or melamine
  • polyphosphates or polyacrylic acid salts such as sodium binders, sodium bicarbonate, sodium
  • the coating composition used according to the method of the present invention is preferably used to produce coated printed or writing paper, or special papers such as cardboard or photographic papers.
  • the coating composition used according to the method of the invention can be applied to the substrate by any conventional process, for example with an air blade, a coating blade, a roller, a doctor blade or a rod, or in the size press, after which the coatings are dried at paper surface temperatures in the range from 70 to 200°C, preferably 90 to 130°C, to a residual moisture content of 3-8%, for example with infra-red driers and/or hot-air driers. Comparably high degrees of whiteness are thus achieved even at low drying temperatures.
  • the coatings obtained are distinguished by optimum distribution of the dispersion fluorescent brightener over the entire surface and by an increase in the level of whiteness thereby achieved, by a high fastness to light and to elevated temperature (e.g. stability for 24 hours at 60-100°C.) and excellent bleed-fastness to water.
  • the present invention provides a method for the fluorescent whitening of a paper surface comprising contacting the paper in the size press with an aqueous solution containing a size, optionally an inorganic or organic pigment and 0.1 to 20g/l of a fluorescent whitening agent having the formula (1).
  • the size is starch, a starch derivative or a synthetic sizing agent, especially a water-soluble copolymer.
  • the brighteners defined above are of particular importance for the treatment of textile fabrics.
  • the treatment of textile substrates is advantageously carried out in an aqueous medium in which the particular optical brighteners are present in a finely divided form (suspensions, so-called microdispersions and in some cases solutions).
  • Dispersing agents, stabilisers, wetting agents and further auxiliaries can optionally be added during the treatment.
  • the treatment is usually carried out at temperatures of from about 20° to 140°C, for example at the boiling point of the bath, or in the region thereof (about 90°C).
  • solutions or emulsions in organic solvents as are used in dyeing practice in so-called solvent dyeing (pad-thermofix method and the exhaustion dyeing process in dyeing machines).
  • optical brighteners which can be used according to the present invention can also be employed, for example, in the following use forms: (a) In mixtures with so-called “carriers”, wetting agents, softeners, swelling agents, antioxidants, light stabilisers, heat stabilisers and chemical bleaching agents (chlorite bleach and bleaching bath additives).
  • carriers wetting agents, softeners, swelling agents, antioxidants, light stabilisers, heat stabilisers and chemical bleaching agents (chlorite bleach and bleaching bath additives).
  • the combined treatment can in many cases advantageously be effected with the aid of corresponding stable formulations which contain the compounds having an optical brightening action in a concentration such that the desired brightening effect is obtained.
  • the full effect of the brightener is achieved by an after-treatment.
  • This can be, for example, a chemical treatment (for example acid treatment), a thermal treatment (for example heat) or a combined chemical/heat treatment.
  • optical brighteners to be used according to the invention can vary within wide limits. A distinct and durable effect can already be achieved with vary small amounts and in certain cases, for example, with amounts of 0.03% by weight. However amounts of up to about 0.5% by weight can also be used. For most cases of interest in practice, amounts of between 0.05 and 0.5% by weight relative to the material to be brightened, are preferably of interest.
  • the optical brighteners are also especially suitable as additives for washing baths or to industrial and household washing agents and they can be added in various ways. They are appropriately added to washing baths in the form of their solutions in water or organic solvents or also in a state of fine division as aqueous dispersions or slurries. They, or their components, are advantageously added to household or industrial washing agents at any phase of the manufacturing process of the washing agent, for example to the so-called "slurry" prior to spray-drying of the washing powder or during the preparation of liquid washing agent combinations.
  • the compounds can be added both in the form of a solution or dispersion in water or other solvents and also without auxiliaries in the form of a dry brightener powder. However, they can also be sprayed, in the dissolved or pre-dispersed form, onto the finished washing agent.
  • Washing agents which can be used are the known mixtures of detergent substances, such as, for example, soap in the form of chips and powders, synthetic products, soluble salts of sulphonic acid half-esters of higher fatty alcohols, arylsulphonic acids, which are substituted by higher alkyl and /or polysubstituted by alkyl, carboxylic acid esters with alcohols of medium to higher molecular weight, fatty acid acylaminoalkyl- or aminoaryl-glycerol- sulphonates, phosphoric acid esters of fatty alcohols and the like.
  • detergent substances such as, for example, soap in the form of chips and powders, synthetic products, soluble salts of sulphonic acid half-esters of higher fatty alcohols, arylsulphonic acids, which are substituted by higher alkyl and /or polysubstituted by alkyl, carboxylic acid esters with alcohols of medium to higher molecular weight, fatty acid acylaminoalkyl
  • washers which can be used are, for example, alkali metal polyphosphates and alkali metal polymeta- phosphates, alkali metal pyrophosphates, alkali metal salts of carboxyethylcellulose and other "soil redeposition inhibitors", and also alkali metal silicates, alkali metal carbonates, alkali metal borates, alkali metal perborates, nitrilotriacetic acid, ethylenediamine-tetraacetic acid and foam stabilisers, such as alkanolamides of higher fatty acids.
  • the washing agents can contain, for example: antistatic agents, superfatting skin protection agents, such as lanolin, enzymes, antimicrobial agents, perfumes and dyestuffs.
  • the brighteners have the particular 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. Also in the presence of perborate or peracids and activators, for example tetraacetylglycoluril or ethylenediamine-tetraacetic acid are the new brighteners very stable both in pulverulent washing agent and in washing baths.
  • 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 new brighteners very stable both in pulverulent washing agent and in washing baths.
  • the brighteners according to the invention are added in amounts of 0.005 to 2% or more and preferably of 0.03 to 0.5%, relative to the weight of the liquid or pulverulent ready-to-use washing agent.
  • wash liquors which contain the indicated amounts of the optical brighteners according to the invention impart a brilliant appearance in daylight.
  • the washing treatment is carried out, for example, as follows:
  • the indicated textiles are treated for 1 to 30 minutes at 5° to 100°C and preferably at 25° to 100°C in a wash bath which contains 1 to 10 g kg of a composite washing agent containing builders and 0.05 to 1% relative to the weight of the washing agent, of the brighteners claimed.
  • the liquor ratio can be 1 :3 to 1 :50.
  • the wash bath can contain, as a bleach additive, 0.2 g/l of active chlorine (for example in the form of hypochlorite) or 0.1 to 2 g/l of sodium perborate.
  • the brighteners according to the invention can also be applied from a rinsing bath with a "carrier".
  • the brightener is incorporated in a soft rinsing agent or in another rinsing agent, which contains, as the "carrier", for example, polyvinyl alcohol, starch, copolymers on an acrylic basis or formaldehyde/urea or ethylene-urea or propylene-urea derivatives, in amounts of 0.005 to 5% or more and preferably of 0.2 to 2%, relative to the rinsing agent.
  • rinsing agents of this type When used in amounts of 1 to 100 ml, and preferably of 2 to 25 ml, per litre of rinsing bath, rinsing agents of this type, which contain the brighteners according to the invention, impart brilliant brightening effects to very diverse types of treated textiles.
  • the compounds described in Table 2 are firstly applied to cotton and polyamide fabric samples using the pad-batch process as described in a) above. Subsequently, the cotton sample is added to 200ml. of a liquor containing 10g/l. of sodium sulphate, whilst the polyamide sample is introduced into a bath which was buffered at pH 7 with the aid of a phosphate buffer.
  • the 2 baths are then heated from 25 to 100°C over 35 minutes, held at 100°C for a further 30 minutes and then cooled to room temperature.
  • the samples are then rinsed, spin-dried and ironed at 160°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne de nouveaux composés représentés par la formule (1) dans laquelle chaque R1 représente indépendamment, un résidu alkyl- ou diallylamino, chaque R2 représente indépendamment, un groupe phénylamino substitué ou non par un ou plusieurs groupes alkyle C1-C4, atomes d'halogène, de cyano, groupes SO3M, -SO2NH2, alkyle SO2NHC1-C4, -CO2M, alkyle CO2C1-C4, -CONH2, alkyle -CONHC1-C4-, ou groupes alkyle NHCOC1-C4, à condition que le groupe phénylamino ne soit pas substitué par deux groupes SO3Na, ou un résidu allyl- ou diallylamino et M représente un atome de métal alcalin ou un atome de métal terreux alcalin, un ammonium ou un cation formé à partir d'une amine et leur utilisation en tant qu'azureur optique pour des matières organiques naturelles ou synthétiques, notamment du coton et du polyamide.
PCT/EP2000/012200 1999-12-14 2000-12-05 Derives allyl- et diallylaminotriazinylaminostilbene et leur utilisation en tant qu'azureur optique WO2001044210A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU30062/01A AU3006201A (en) 1999-12-14 2000-12-05 Allyl- and diallylaminotriazinylaminostilbene derivatives and their use as optical brightening

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP99811157.9 1999-12-14
EP99811157 1999-12-14

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WO2001044210A1 true WO2001044210A1 (fr) 2001-06-21

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007145577A1 (fr) 2006-06-15 2007-12-21 Holmen Aktiebolag Procédé de stabilisation de la blancheur d'un ou de plusieurs agents d'azurage optique (fwa) compris dans une sauce de collage/couchage pour le traitement de surface de papiers et des couches de traitement de surface formées à partir de celles-ci
US8740997B2 (en) 2010-05-18 2014-06-03 Milliken & Company Optical brighteners and compositions comprising the same
CN112334615A (zh) * 2018-05-18 2021-02-05 斯道拉恩索公司 用于纸和纸板的涂料组合物
CN112352078A (zh) * 2018-05-18 2021-02-09 斯道拉恩索公司 用于纸和纸板的涂料组合物
CN114381073A (zh) * 2021-12-15 2022-04-22 楷模居品（江苏）有限公司 一种抗紫外老化的壳聚糖-聚氯乙烯木塑板及制备方法

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JPS5278235A (en) * 1975-12-25 1977-07-01 Showa Kagaku Kougiyou Kk Process for manufacture of 4*4**bistriazinylaminoo stilbenee2*22disulfonic acid derivatives
EP0922699A1 (fr) * 1997-12-13 1999-06-16 Ciba SC Holding AG Composés stilbéniques asymétriques utilisables comme agents antisolaire

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EP0922699A1 (fr) * 1997-12-13 1999-06-16 Ciba SC Holding AG Composés stilbéniques asymétriques utilisables comme agents antisolaire

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007145577A1 (fr) 2006-06-15 2007-12-21 Holmen Aktiebolag Procédé de stabilisation de la blancheur d'un ou de plusieurs agents d'azurage optique (fwa) compris dans une sauce de collage/couchage pour le traitement de surface de papiers et des couches de traitement de surface formées à partir de celles-ci
EP2027336A1 (fr) * 2006-06-15 2009-02-25 Holmen Aktiebolag Procédé de stabilisation de la blancheur d'un ou de plusieurs agents d'azurage optique (fwa) compris dans une sauce de collage/couchage pour le traitement de surface de papiers et des couches de traitement de surface formées à partir de celles-ci
EP2027336A4 (fr) * 2006-06-15 2012-09-12 Holmen Aktiebolag Procédé de stabilisation de la blancheur d'un ou de plusieurs agents d'azurage optique (fwa) compris dans une sauce de collage/couchage pour le traitement de surface de papiers et des couches de traitement de surface formées à partir de celles-ci
US9493913B2 (en) 2006-06-15 2016-11-15 Holmen Ab Method for stabilizing the whiteness of fluorescent whitening agent(s)(FWA) included in surface-treatment size/coating slip for paper and of surface-treatment layers formed thereof
US8740997B2 (en) 2010-05-18 2014-06-03 Milliken & Company Optical brighteners and compositions comprising the same
CN112334615A (zh) * 2018-05-18 2021-02-05 斯道拉恩索公司 用于纸和纸板的涂料组合物
CN112352078A (zh) * 2018-05-18 2021-02-09 斯道拉恩索公司 用于纸和纸板的涂料组合物
CN114381073A (zh) * 2021-12-15 2022-04-22 楷模居品（江苏）有限公司 一种抗紫外老化的壳聚糖-聚氯乙烯木塑板及制备方法
CN114381073B (zh) * 2021-12-15 2023-09-29 珠海市睿住建筑科技有限公司 一种抗紫外老化的壳聚糖-聚氯乙烯木塑板及制备方法

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AU3006201A (en) 2001-06-25

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