EP1153011A1 - Bis-styrylbiphenyl compounds - Google Patents

Bis-styrylbiphenyl compounds

Info

Publication number
EP1153011A1
EP1153011A1 EP00904986A EP00904986A EP1153011A1 EP 1153011 A1 EP1153011 A1 EP 1153011A1 EP 00904986 A EP00904986 A EP 00904986A EP 00904986 A EP00904986 A EP 00904986A EP 1153011 A1 EP1153011 A1 EP 1153011A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
hydrogen
compound
alkoxy
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.)
Withdrawn
Application number
EP00904986A
Other languages
German (de)
English (en)
French (fr)
Inventor
Stefan Ohren
Dieter Reinehr
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 EP00904986A priority Critical patent/EP1153011A1/en
Publication of EP1153011A1 publication Critical patent/EP1153011A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
    • 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
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds

Definitions

  • the present invention relates to novel asymmetrical bis-styrylbiphenyl compounds, to a process for their preparation and to their use as optical brighteners, in particular for polyester spinning melts.
  • Bis-styrylbiphenyl compounds which are suitable as optical brighteners are already known, e.g. from GB-A-1 , 247,934 which also discloses processes for their preparation. However, those processes provide almost exclusively symmetrical compounds, i.e. compounds which carry the same substituents in the same positions at the terminal phenyl radicals.
  • the preparation of asymmetrical bis-styrylbiphenyl compounds is described only in admixture with symmetrical compounds from which they must be separated by elaborate measures, e.g. by recrystallisation. Naturally, the resulting yield of asymmetrical compounds is unsatisfactory.
  • this invention relates to asymmetrical bis-styrylbiphenyl compounds of formula
  • R, and R 2 are each independently of the other hydrogen, cyano, halogen, hydroxy, alkyl, cycloalkyl, alkoxy, carboxy, alkoxycarbonyl, alkylcarbonyioxy, aryl oraralkyl, wherein R, and
  • R are not both hydrogen at the same time and which substituents are different if they are in the same position of the phenyl ring, and
  • R 3 , R , R5 and R 6 are each independently of one another hydrogen, halogen, alkyl, cycloalkyl or alkoxy.
  • Ri and R 2 are each independently of the other hydrogen, cyano, halogen, hydroxy, alkyl, cycloalkyl, alkoxy, carboxy, alkoxycarbonyl, alkylcarbonyloxy, aryl or aralkyl, at least one of which substituents is not hydrogen, and
  • R3, R , s and R 6 are each independently of one another hydrogen, halogen, alkyl or alkoxy.
  • R1 and R 2 are independently of each other cyano, chloro, hydroxy, C C 4 alkyl, C C 4 alkoxy or phenyl.
  • R 3 to R 6 are preferably each independently of one another hydrogen, chloro, C C 4 alkyl or C r C 4 alkoxy. In particularly preferred compounds of formula (1) or (2), all of these substituents are hydrogen.
  • Halogen is fluoro, bromo, iodo or, preferably, chloro.
  • alkyl groups in the alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy and aralkyl radicals contain, for example, 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms and, most preferably, 1 to 4 carbon atoms.
  • alkyl is preferably C C alkyl, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl.
  • Cycloalkyl is preferably Cs-C ⁇ ycloalkyl, more preferably cyclohexyl.
  • Alkoxy preferably means C C 4 alkoxy, for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and tert-butoxy.
  • Aryl is, for example, naphthyl or, preferably, phenyl, and these radicals can be substituted, for example by alkyl, alkoxy, sulfo, carboxy, halogen or alkoxycarbonyl.
  • Aralkyl preferably means C C 4 alkylenephenyl, more preferably benzyl.
  • R is hydrogen, cyano, halogen, hydroxy, alkyl, alkoxy, carboxy, alkoxycarbonyl, alkylcarbonyloxy, aryl or aralkyl.
  • Rt is C 1 -C 2 alkyl, CrC-salkoxy, cyano or phenyl.
  • the compounds of formula (1 ) are prepared, for example, by reacting 1 mole of a dialdehyde of formula
  • R 3 , R . Rs and R 6 are each independently of one another hydrogen, halogen, alkyl or alkoxy, with 1 mole of a compound of formula
  • R T is hydrogen, cyano, halogen, hydroxy, alkyl, cycloalkyl, alkoxy, carboxy, alkoxycarbonyl, alkylcarbonyloxy, aryl or aralkyl, and
  • R 7 and R 8 are alkyl, cycloalkyl, aryl or aralkyl, to give an intermediate of formula
  • R 2 is hydrogen, cyano, halogen, hydroxy, alkyl, cycloalkyl, alkoxy, carboxy, alkoxycarbonyl, alkylcarbonyloxy, aryl or aralkyl, and
  • R 7 and R 8 are alkyl, cycloalkyl, aryl or aralkyl, wherein Ri and R 2 are not both hydrogen at the same time and which substituents are different if they are in the same position of the phenyl ring, to give a compound of formula (1).
  • R 7 and R 8 are preferably C ⁇ -C 4 alkyl, phenyl or benzyl. In particularly preferred compounds of formula (5) and (7) these substituents are d-Caalkyl.
  • the compounds (4), (5) and (7) are known or can be prepared in a manner known per se.
  • the reaction of a compound of formula (4) with a compound of formula (5) and the reaction of an intermediate of formula (6) with a compound of formula (7) are carried out in the presence of a strongly basic compound.
  • a strongly basic compound are for example: alkali metal hydroxides, alkali metal amides, alkali metal carbonates, alkali metal hydrogen- carbonates or alkali metal alcoholates, in particular the lithium, potassium or sodium compounds.
  • the potassium or sodium alcoholates of aliphatic C 1 -C 4 alcohols are particularly preferred.
  • the solvent used for the reaction of a compound of formula (4) with a compound of formula (6) is a solvent which is inert towards the reactants, preferably an aliphatic alcohol and, more preferably, a CrC 6 alcohol.
  • Suitable are, for example, methanol, ethanol, n-propanol, isopro- panol, butan-1-ol, butan-2-ol, tert-butanol, pentan-1-ol and hexan-1-ol. Of these, methanol is preferred.
  • the reaction temperature is usually in the range from room temperature to the boiling temperature of the solvent. It is preferred to work at about 20 to 80° C, more preferably at 30 to 70° C.
  • the reaction time depends, inter alia, on the kind of reactants used and on the reaction temperature.
  • the temperature is usually in the range from 2 to 48 hours.
  • Ri is hydrogen, cyano, halogen, hydroxy, alkyl, cycloalkyl, alkoxy, carboxy, alkoxycarbonyl, alkylcarbonyloxy, aryl or aralkyl, and
  • R3, R 4 , R 5 and R 6 are each independently of one another hydrogen, halogen, alkyl or alkoxy, at least one of the substituents R 3 , R 4 , R5 and R 6 not being hydrogen, are novel and are also an object of this invention.
  • an aprotic solvent is used which is inert towards the reactants and in which the compound of formula (6) is at least partially soluble. It is possible to use e.g. dimethylformamide, diethylformamide, di- methylacetamide, dimethylsulfoxide and N-methylpyrrolidone.
  • the reaction temperature is usually in the range from room temperature to the boiling temperature of the solvent. It is preferred to work at about 20 to 80° C, more preferably at 20 to 40° C.
  • the reaction time depends, inter alia, on the kind of reactants used and on the reaction temperature and is generally in the range from 2 to 48 hours.
  • the reaction mixture is worked up in customary manner and the compound of formula (1) is isolated, e.g. by evaporation or by filtration if it is insoluble in the solvent used.
  • the compounds of formula (1) have marked fluorescence in the dissolved or finely divided state. They can thus be used for optically brightening a range of materials, in particular organic materials.
  • This invention thus also relates to the use of the compounds of formula (1 ) for optically brightening organic materials, and to organic materials comprising at least one compound of formula (1), as well as to a process for optically brightening organic materials, which process comprises incorporating into, or applying to, these materials at least one compound of formula (1).
  • the organic materials which can be brightened according to this invention by means of compounds of formula (1) include synthetic, semi-synthetic or natural, especially polymeric, materials.
  • Suitable materials are, for example, a) polymerisation products based on organic compounds containing at least one polyme- risable carbon-carbon double bond, for example polymers based on unsaturated carboxylic acids or derivatives thereof (such as acryl esters, acrylic acids, acrylonitrile and their derivatives), on olefin hydrocarbons (such as ethylene, propylene, styrene) or on vinyl compounds or vinylidene compounds (such as vinyl chloride, vinyl alcohol, vinylidene chloride); b) polymerisation products which are obtainable by ring-opening, for example polyamides of the caprolactam type, and also polymers which are obtainable both via polyaddition and via polycondensation, such as polyethers or polyacetals; c) polycondensates, such as polyesters, polyamides, melamine
  • novel compounds are particularly preferably used for optically brightening polyesters, in particular polyethylene glycol terephthalate, in the spinning melt, since they do not decompose at the required temperatures.
  • novel asymmetrical compounds of formula (1) have a higher degree of whiteness on the cited materials than the corresponding symmetrical compounds. They are furthermore distinguished by particularly good fastness to sublimation.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP00904986A 1999-02-11 2000-01-31 Bis-styrylbiphenyl compounds Withdrawn EP1153011A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP00904986A EP1153011A1 (en) 1999-02-11 2000-01-31 Bis-styrylbiphenyl compounds

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP99810119 1999-02-11
EP99810119 1999-02-11
PCT/EP2000/000726 WO2000047550A1 (en) 1999-02-11 2000-01-31 Bis-styrylbiphenyl compounds
EP00904986A EP1153011A1 (en) 1999-02-11 2000-01-31 Bis-styrylbiphenyl compounds

Publications (1)

Publication Number Publication Date
EP1153011A1 true EP1153011A1 (en) 2001-11-14

Family

ID=8242673

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00904986A Withdrawn EP1153011A1 (en) 1999-02-11 2000-01-31 Bis-styrylbiphenyl compounds

Country Status (7)

Country Link
EP (1) EP1153011A1 (ko)
JP (1) JP2002536506A (ko)
KR (1) KR20010101802A (ko)
CN (1) CN1364154A (ko)
AU (1) AU2668000A (ko)
ID (1) ID29984A (ko)
WO (1) WO2000047550A1 (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6800274B2 (en) 2002-09-17 2004-10-05 The C.P. Hall Company Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
CN102911509A (zh) * 2012-10-26 2013-02-06 山西青山化工有限公司 一种二苯乙烯基联苯型荧光增白剂的环保制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH582134A5 (ko) * 1973-11-19 1976-11-30 Ciba Geigy Ag
DE3001065A1 (de) * 1980-01-12 1981-07-16 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von optischen aufhellern
DE3176183D1 (en) * 1980-12-12 1987-06-19 Ciba Geigy Ag 4-styryl-4'-vinylbifenyls, methods for their preparation and their use as optical whiteners
US4666627A (en) * 1983-05-08 1987-05-19 Ciba-Geigy Corporation 4-Heterocyclylvinyl-4-'styryl-biphenyls
DE4330968A1 (de) * 1993-09-13 1995-03-16 Basf Ag Aufhellermischungen auf Basis von Bisstyrylverbindungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0047550A1 *

Also Published As

Publication number Publication date
CN1364154A (zh) 2002-08-14
AU2668000A (en) 2000-08-29
KR20010101802A (ko) 2001-11-14
WO2000047550A1 (en) 2000-08-17
ID29984A (id) 2001-10-25
JP2002536506A (ja) 2002-10-29

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