WO1996000220A1 - Derives de s-triazinylaminostilbene et leur utilisation en tant qu'agents d'azurage optique - Google Patents

Derives de s-triazinylaminostilbene et leur utilisation en tant qu'agents d'azurage optique Download PDF

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Publication number
WO1996000220A1
WO1996000220A1 PCT/GB1995/001428 GB9501428W WO9600220A1 WO 1996000220 A1 WO1996000220 A1 WO 1996000220A1 GB 9501428 W GB9501428 W GB 9501428W WO 9600220 A1 WO9600220 A1 WO 9600220A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
alkyl
phenyl
halogen
substituted
Prior art date
Application number
PCT/GB1995/001428
Other languages
English (en)
Inventor
John Dennis Thompson
Original Assignee
Hickson International Plc
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 Hickson International Plc filed Critical Hickson International Plc
Priority to EP95922602A priority Critical patent/EP0766677A1/fr
Publication of WO1996000220A1 publication Critical patent/WO1996000220A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
    • D06P1/382—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group directly attached to heterocyclic group
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching

Definitions

  • the present invention relates to novel s-triazinylaminostilbene derivatives, processes and intermediates for their preparation and their use as optical whitening agents (OWAs) for whitening natural, synthetic and semi-synthetic polymers.
  • OWAs optical whitening agents
  • s-triazinylaminostilbene OWAs The area of use covered by s-triazinylaminostilbene OWAs is very broad, but of particular interest is the whitening of paper and textile substrates by the class of triazinylaminostilbene derivatives known as the "hexasulphonated" compounds resulting from the use of aniline-2,5-disulphonic acid as one of the substituents.
  • OWA to cellulose for example is generally a function of the number of solubilising groups (particularly sulphonic acids) present.
  • the disulphonic acid derivatives such as 4,4'-bis(6"-phenylamino-4 ,1 -morpholino- l",3 ,5"-triazin-2"-yl)aminostilbene-2,2'-disulphonic acid
  • the tetrasulphonic acid derivatives such as 4,4'-bis[6"-(4'"-suIphophenylamino)- 4 " - morpholino-1 " ,3" ,5"-triazin-2"-yl]aminostilbene-2,2'-disulphonic acid
  • the hexasulphonic acid derivatives such as 4,4'-bis[6"-
  • tetrasulphonic acids are thus especially useful for application to paper either alone, or in combination with other optical whitening agents, dyestuffs, pigments or other additives by size press or other surface application methods, and to textiles by padding, either alone or in combination with other typical textile finishing additives e.g. acid resins, crease- and water-proofmg agents, or specialist finishes, or during laundering processes as part of detergent or fabric conditioner compositions.
  • typical textile finishing additives e.g. acid resins, crease- and water-proofmg agents, or specialist finishes, or during laundering processes as part of detergent or fabric conditioner compositions.
  • novel s-triazinylaminostilbene derivatives according to the invention are compounds of formula (1)
  • Y is halogen (e.g. fluoro, chloro or bromo), alkoxy (e.g. C alkoxy) or -NR 2 R 3 [ where R 2 and R 3 are the same or different and are H, alkyl (e.g. C alkyl), hydroxy ⁇ alkyl (e.g. C M hydroxyalkyl), or aryl (e.g. phenyl, optionally substituted), or together with the nitrogen atom form a substituted or unsubstituted cyclic amino group having 5-7 ring members, e.g. morpholino or piperidino],
  • R 2 and R 3 are the same or different and are H, alkyl (e.g. C alkyl), hydroxy ⁇ alkyl (e.g. C M hydroxyalkyl), or aryl (e.g. phenyl, optionally substituted), or together with the nitrogen atom form a substituted or unsubstituted cyclic amino group having 5-7 ring members,
  • R is H, aryl (e.g. phenyl), which is unsubstituted or substituted (e.g. by one or more electron releasing groups such as C alkyl and/or C M alkoxy),
  • R 1 is H or alkyl (e.g. C M alkyI, optionally substituted),
  • Z is an electron-withdrawing group (e.g. CN, -SO ⁇ ),
  • x 2 or 3
  • M is H, a metal cation (e.g. alkali metal, such as Na, K or Li) or -N + R R 5 R 6 R 7 (where R 4 -R 7 are the same or different and are H, alkyl (e.g. C M alkyl), aralkyl (e.g. phenyl(C j . 6 )-alkyl) or hydroxyalkyl (e.g. C M hydroxyalkyl)).
  • Y is preferably bis(2-hydroxyethyl)amino or morpholino.
  • R is preferably phenyl or substituted phenyl, e.g.
  • R 1 is preferably H or -CH 3 and Z is preferably -S0 3 M (particularly where M is an alkali metal cation such as Na) or CN.
  • a compound of particular importance is the compound in which Y is bis(2- hydroxyethyl)amino, R is phenyl, R 1 is H and Z is -S0 3 Na.
  • the compounds of formula (1) can be prepared by reacting a compound of formula (2)
  • X is halogen (e.g. fluoro, chloro or bromo)
  • Y is halogen (e.g. fluoro, chloro or bromo) or alkoxy (e.g. C ⁇ alkoxy) and N(R)CHR f Z is as defined above) with 4,4'- diaminostilbene-2,2'-disulphonic acid.
  • the reaction can be carried out at any convenient temperature (e.g. 20-60°C or to reflux) in a suitable solvent (e.g. water or aqueous acetone), preferably in the presence of an acid binding agent such as sodium bicarbonate or carbonate.
  • a suitable solvent e.g. water or aqueous acetone
  • the compounds of formula (2) which also form part of the invention, may be prepared by reacting a cyanuric halide of formula (3)
  • the amines (4) may be prepared by reacting an amine RNH 2 with an alcohol HOCHR'Z, for example in a neutral aqueous or aqueous alcoholic medium at 20- 60°C.
  • a soluble cyanide e.g. NaCN, KCN
  • me compounds of formula (1) lie in the optical whitening of paper and textiles under conditions normally used for me "hexasulphonic acid derivatives" referred to above.
  • diey may also be used to treat any other cellulosic or otfier natural, synmetic or semi- syndietic materials to which optical brightening is relevant.
  • Tetra-sodium 4.4'bis ⁇ 6"-N-phenyl-N-sulphonatomethylamino-4''-bis( ' 2" , - hydroxyethyl)amino-l".3".5"-triazin-2"-yl]aminostilbene-2.2'-disulphonate To a solution of sodium N-phenyl-N-(2,4-dichloro-l,3,5-triazin-6-yl)aminomemane sulphonate (37.5g, 0.105g.
  • the starting material is prepared as follows:
  • a solution of cyanuric chloride (19.4g, 0.105. mol.) in acetone (200ml) containing sodium bicarbonate (8.8g, 0.105g.mol.) is cooled to -10°C, and an ice-cold solution of sodium ⁇ -anilinomethane sulphonate (23.0g, OJlOg.mol.) in water (175ml) is added as rapidly as possible and me mixture is allowed to warm up to room temperature.
  • the reaction may be followed by means of HPLC using detection at 265nm to enable visualisation of all me starting products and final products, (including any by-products) to be observed.
  • the resulting solution of me title compound may then be used for further condensations wim nucleophiles, e.g. 4,4'- diaminostilbene-2,2'-disulphonic acid and other amines as required.
  • the solution of sodium ⁇ -anilinomethane sulphonate is prepared as follows. Aniline (10.2g, 0.110 g.mol) is added to a stirred solution of the sodium salt of the formaldehyde bisulphite addition complex (15.4g, 0.115 g.mol) in water (100ml) at 25-30°C. Formation of the sodium phenylaminomethane sulphonate is complete within 90 minutes (less at higher temperatures) and the solution may then be diluted and cooled and used as described above.
  • Tetra-sodium 4.4 ' -b isf ⁇ " -N-phenyl-N-sulphonatomethylamino-4 " -morpholino- 1 " .3 ⁇ 5"-triazin-2 w -yl1aminostilbene-2.2'-disulphonate
  • the above compound is prepared by me method of Example 1 except that the diethanolamine is replaced witii morpholine (lO.Og, 0.115g. mol.) to give the corresponding morpholine derivative.
  • the product may be isolated by salting followed by filtration.
  • aniline used in the preparation of the starting material in Examples 1 and 2 may be replaced by p-toluidine (11.8g, O.llOg.mol.) or p-anisidine (13.5g, O.llOg.mol.) to give the corresponding derivatives.
  • Cyanuric chloride (18.5g) is added all at once to a stirred, ice-cold slurry of phenylaminoacetonitrile (13.9g) in water (150ml) containing sodium bicarbonate (8.4g) and the mixture is allowed to warm up to room temperature.
  • the resulting slurry of the title compound may then be used for further condensations wim nucleophiles, e.g. 4,4'-diaminostilbene-2,2'-disulphonic acid and other amines as required.
  • the slurry of phenylaminoacetonitrile is prepared as follows. Aniline (9.8g) is added to a stirred solution of glycolonitrile (55% aqueous solution, 11.5g) in water (100ml) at 20°C, warmed up to 60°C and maintained at mat temperature until the reaction is complete (ca. 1 hour). The resulting oily dispersion may then be cooled and diluted and used as described above.
  • Blank handsheets (comprised of 27.2% bleached kraft softwood, 52.8% bleached kraft hardwood and 20% calcium carbonate filler internally sized wim alkyl ketene dimer) are passed through 9% clear starch solution at pH 6 containing 30, 40 and 50 g/1 of OWA (optical strength (E ll ⁇ t )62) and then fed through a size press to squeeze out me excess liquor.
  • OWA optical strength
  • Patterns of 80 x 80 bleached cotton fabric are passed through solutions of OWAs containing 5,10,15 and 20 g/1 of OWA of optical strength (E ⁇ ) adjusted to 65, and men fed tiirough a padding mangle at constant pressure to give 100% wt/wt pick-up of liquor.
  • the padding solutions contain (in addition to the OWA) 100 g/1 Fixapret 00 CPN and 10 g/1 magnesium chloride.
  • the OWAs used are (i) that of Example 2 and (ii) a "hexa-sulpho" OWA based on aniline- 2,5-disulphonic acid and morpholine. The patterns are dried for 5 minutes at 140°C

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Paper (AREA)

Abstract

Dérivés de s-triazinylaminostilbène représentés par la formule (1) dans laquelle Y représente halogène, alcoxy ou-NR?2R3 (R2 et R3¿ étant semblables ou différents et représentant H, hydroxyalkyle ou aryle ou, avec l'atome d'azote, constituant un groupe amino cyclique substitué ou insubstitué possédant 5-7 éléments), R représente H, aryle substitué ou insubstitué (par exemple, par un ou plusieurs groupes de libération d'électrons, tels que alkyle C¿1-4? et/ou alcoxy C1-4), R?1¿ représente H ou alkyle, Z représente un groupe de retrait d'électrons (par exemple, CN, -SO¿x?M), x est 2 ou 3 et M représente -H, un cation de métal ou N?+R4R5R6R7 (R4-R7¿ étant semblables ou différents et représentant H, alkyle, aralkyle ou hydroxyalkyle). Ces composés sont efficaces en tant qu'agents d'azurage optique pour du papier ou des textiles.
PCT/GB1995/001428 1994-06-24 1995-06-19 Derives de s-triazinylaminostilbene et leur utilisation en tant qu'agents d'azurage optique WO1996000220A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP95922602A EP0766677A1 (fr) 1994-06-24 1995-06-19 Derives de s-triazinylaminostilbene et leur utilisation en tant qu'agents d'azurage optique

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9412756A GB9412756D0 (en) 1994-06-24 1994-06-24 Chemical compounds
GB9412756.0 1994-06-24

Publications (1)

Publication Number Publication Date
WO1996000220A1 true WO1996000220A1 (fr) 1996-01-04

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EP (1) EP0766677A1 (fr)
GB (1) GB9412756D0 (fr)
IL (1) IL114228A0 (fr)
WO (1) WO1996000220A1 (fr)
ZA (1) ZA955278B (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0860437A1 (fr) * 1997-02-18 1998-08-26 Bayer Ag Procédé de préparation des acides 4,4'-diaministilbènes-2,2'-disulfoniques substitués
WO2001019804A1 (fr) * 1999-09-10 2001-03-22 Ciba Specialty Chemicals Holding Inc. Derives de triazinylaminostilbene tenant lieu d'agents eclaircissants fluorescents
WO2004005617A1 (fr) * 2002-07-05 2004-01-15 Ciba Specialty Chemicals Holding Inc. Melanges d'acides disulphoniques triazinylaminostilbene
WO2009150182A1 (fr) * 2008-06-11 2009-12-17 Kemira Germany Gmbh Compositions d’agent de blanchiment fluorescent
EP1674616A3 (fr) * 2002-11-19 2010-02-03 Basf Se Agents de blanchiment fluorescents amphotères
KR20100135845A (ko) * 2008-03-26 2010-12-27 클라리언트 파이넌스 (비브이아이)리미티드 개선된 형광 증백 조성물
US8740997B2 (en) 2010-05-18 2014-06-03 Milliken & Company Optical brighteners and compositions comprising the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2124079A1 (de) * 1970-05-18 1971-12-02 Imperial Chemical Industries Ltd., London Optische Aufheller
JPS4910216A (fr) * 1972-05-26 1974-01-29
JPS4932923A (fr) * 1972-07-27 1974-03-26
JPH0221014A (ja) * 1988-07-08 1990-01-24 Osaka Gas Co Ltd ねじ

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2124079A1 (de) * 1970-05-18 1971-12-02 Imperial Chemical Industries Ltd., London Optische Aufheller
JPS4910216A (fr) * 1972-05-26 1974-01-29
JPS4932923A (fr) * 1972-07-27 1974-03-26
JPH0221014A (ja) * 1988-07-08 1990-01-24 Osaka Gas Co Ltd ねじ

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 68, no. 20, 13 May 1968, Columbus, Ohio, US; abstract no. 88211g, OKUBO I. ET AL.: "Stilbene fluorescent brightening agents" page 8524; column 2; *
CHEMICAL ABSTRACTS, vol. 69, no. 7, 12 August 1968, Columbus, Ohio, US; abstract no. 27392r, TEMKINA V.Y. ET AL.: "New fluorescent complexons in the bis(triazinyl-amino)stilbene series" page 2555; column 2; *
CHEMICAL ABSTRACTS, vol. 80, no. 18, 6 May 1974, Columbus, Ohio, US; abstract no. 97352d, PIRKL J.: "Fluorescent whiteners" page 77; column 2; *
CHEMICAL ABSTRACTS, vol. 81, no. 22, 2 December 1974, Columbus, Ohio, US; abstract no. 137605t, OHTAKI E. ET AL.: "Fluorescent whiteners" page 76; column 2; *
CHEMICAL ABSTRACTS, vol. 81, no. 8, 26 August 1974, Columbus, Ohio, US; abstract no. 38963b, MATSUO M. ET AL.: "Stilbenedisulfonic acid fluorescent whiteners" page 91; column 2; *
TR. VSES. NAUCH.-ISSLED. INST. KHIM. REAKTIVOV OSOBO CHIST. KHIM. VESHCHESTV, no. 30, pages 131 - 144 *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6025490A (en) * 1997-02-18 2000-02-15 Bayer Aktiengesellschaft Process for the preparation of substituted 4,4'-diaminostilbene-2,2'-disulphonic acids
EP0860437A1 (fr) * 1997-02-18 1998-08-26 Bayer Ag Procédé de préparation des acides 4,4'-diaministilbènes-2,2'-disulfoniques substitués
US6723846B1 (en) 1999-09-10 2004-04-20 Ciba Specialty Chemicals Corporation Triazinylaminostilbene derivative as fluorescent whitening agents
WO2001019804A1 (fr) * 1999-09-10 2001-03-22 Ciba Specialty Chemicals Holding Inc. Derives de triazinylaminostilbene tenant lieu d'agents eclaircissants fluorescents
WO2004005617A1 (fr) * 2002-07-05 2004-01-15 Ciba Specialty Chemicals Holding Inc. Melanges d'acides disulphoniques triazinylaminostilbene
US7270771B2 (en) 2002-07-05 2007-09-18 Ciba Specialty Chemicals Corporation Triazinylaminostilbene disulphonic acid mixtures
EP2292837A1 (fr) * 2002-07-05 2011-03-09 Basf Se Mélanges d'acides disulphoniques de triazinylstilbene
EP1674616A3 (fr) * 2002-11-19 2010-02-03 Basf Se Agents de blanchiment fluorescents amphotères
US8821688B2 (en) 2008-03-26 2014-09-02 Clariant Finance (Bvi) Limited Optical brightening compositions
USRE46913E1 (en) 2008-03-26 2018-06-26 Archroma Ip Gmbh Optical brightening compositions
KR101631871B1 (ko) 2008-03-26 2016-06-20 아르크로마 아이피 게엠베하 개선된 형광 증백 조성물
KR20100135845A (ko) * 2008-03-26 2010-12-27 클라리언트 파이넌스 (비브이아이)리미티드 개선된 형광 증백 조성물
JP2011515547A (ja) * 2008-03-26 2011-05-19 クラリアント・ファイナンス・（ビーブイアイ）・リミテッド 改善された光学的増白組成物
WO2009150182A1 (fr) * 2008-06-11 2009-12-17 Kemira Germany Gmbh Compositions d’agent de blanchiment fluorescent
US8354041B2 (en) 2008-06-11 2013-01-15 Blankophor Gmbh & Co. Kg Composition and process for whitening paper
AU2009256609B2 (en) * 2008-06-11 2013-08-22 Blankophor Gmbh & Co. Kg Composition and process for whitening paper
TWI418684B (zh) * 2008-06-11 2013-12-11 Blankophor Gmbh & Co Kg 螢光增白劑組成物
US8608907B2 (en) 2008-06-11 2013-12-17 Blankophor Gmbh & Co. Kg Fluorescent whitening agent compositions
RU2502838C2 (ru) * 2008-06-11 2013-12-27 БЛАНКОФОР ГмбХ & Ко. КГ Композиции флуоресцентного отбеливающего агента
RU2505636C2 (ru) * 2008-06-11 2014-01-27 БЛАНКОФОР ГмбХ & Ко. КГ Композиция и способ для отбеливания бумаги
JP2011522971A (ja) * 2008-06-11 2011-08-04 ブランコファー ゲーエムベーハー ウント コー．カーゲー 紙を増白するための組成物及びプロセス
EP2135997A1 (fr) * 2008-06-11 2009-12-23 Kemira Germany GmbH Composition et processus pour papier blanchi
WO2009150180A1 (fr) * 2008-06-11 2009-12-17 Kemira Germany Gmbh Composition et processus de blanchiment de papier
US8740997B2 (en) 2010-05-18 2014-06-03 Milliken & Company Optical brighteners and compositions comprising the same

Also Published As

Publication number Publication date
IL114228A0 (en) 1995-10-31
GB9412756D0 (en) 1994-08-17
EP0766677A1 (fr) 1997-04-09
ZA955278B (en) 1996-12-27

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